WO1998039347A3 - Synthesis of l-ribose and 2-deoxy l-ribose - Google Patents
Synthesis of l-ribose and 2-deoxy l-ribose Download PDFInfo
- Publication number
- WO1998039347A3 WO1998039347A3 PCT/US1998/004302 US9804302W WO9839347A3 WO 1998039347 A3 WO1998039347 A3 WO 1998039347A3 US 9804302 W US9804302 W US 9804302W WO 9839347 A3 WO9839347 A3 WO 9839347A3
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- ribose
- deoxy
- yield
- converted
- hydrolysis
- Prior art date
Links
- ASJSAQIRZKANQN-UHNVWZDZSA-N 2-deoxy-L-arabinose Chemical compound OC[C@H](O)[C@H](O)CC=O ASJSAQIRZKANQN-UHNVWZDZSA-N 0.000 title abstract 8
- PYMYPHUHKUWMLA-MROZADKFSA-N aldehydo-L-ribose Chemical compound OC[C@H](O)[C@H](O)[C@H](O)C=O PYMYPHUHKUWMLA-MROZADKFSA-N 0.000 title abstract 7
- 230000015572 biosynthetic process Effects 0.000 title abstract 2
- 238000003786 synthesis reaction Methods 0.000 title abstract 2
- PYMYPHUHKUWMLA-UHFFFAOYSA-N arabinose Natural products OCC(O)C(O)C(O)C=O PYMYPHUHKUWMLA-UHFFFAOYSA-N 0.000 abstract 7
- PYMYPHUHKUWMLA-LMVFSUKVSA-N aldehydo-D-ribose Chemical compound OC[C@@H](O)[C@@H](O)[C@@H](O)C=O PYMYPHUHKUWMLA-LMVFSUKVSA-N 0.000 abstract 5
- HMFHBZSHGGEWLO-UHFFFAOYSA-N alpha-D-Furanose-Ribose Natural products OCC1OC(O)C(O)C1O HMFHBZSHGGEWLO-UHFFFAOYSA-N 0.000 abstract 5
- SRBFZHDQGSBBOR-SOOFDHNKSA-N D-ribopyranose Chemical compound O[C@@H]1COC(O)[C@H](O)[C@@H]1O SRBFZHDQGSBBOR-SOOFDHNKSA-N 0.000 abstract 4
- SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 abstract 4
- 230000007062 hydrolysis Effects 0.000 abstract 4
- 238000006460 hydrolysis reaction Methods 0.000 abstract 4
- 150000001299 aldehydes Chemical class 0.000 abstract 3
- CIHZADLBBUAFTD-ZRBLBEILSA-N (2r,3r,4r)-2,3,4-trihydroxy-5-trityloxypentanal Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(OC[C@@H](O)[C@@H](O)[C@@H](O)C=O)C1=CC=CC=C1 CIHZADLBBUAFTD-ZRBLBEILSA-N 0.000 abstract 2
- HMFHBZSHGGEWLO-SOOFDHNKSA-N D-ribofuranose Chemical compound OC[C@H]1OC(O)[C@H](O)[C@@H]1O HMFHBZSHGGEWLO-SOOFDHNKSA-N 0.000 abstract 2
- 230000002829 reductive effect Effects 0.000 abstract 2
- DBGVGMSCBYYSLD-UHFFFAOYSA-N tributylstannane Chemical compound CCCC[SnH](CCCC)CCCC DBGVGMSCBYYSLD-UHFFFAOYSA-N 0.000 abstract 2
- NPOKZMNZAPKSBT-ZRMNMSDTSA-N (3s,4r,5r)-2-bromooxane-3,4,5-triol Chemical compound O[C@@H]1COC(Br)[C@@H](O)[C@@H]1O NPOKZMNZAPKSBT-ZRMNMSDTSA-N 0.000 abstract 1
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 abstract 1
- OZAIFHULBGXAKX-VAWYXSNFSA-N AIBN Substances N#CC(C)(C)\N=N\C(C)(C)C#N OZAIFHULBGXAKX-VAWYXSNFSA-N 0.000 abstract 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- DJOWTWWHMWQATC-KYHIUUMWSA-N Karpoxanthin Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1(O)C(C)(C)CC(O)CC1(C)O)C=CC=C(/C)C=CC2=C(C)CC(O)CC2(C)C DJOWTWWHMWQATC-KYHIUUMWSA-N 0.000 abstract 1
- 238000006859 Swern oxidation reaction Methods 0.000 abstract 1
- MJOQJPYNENPSSS-XQHKEYJVSA-N [(3r,4s,5r,6s)-4,5,6-triacetyloxyoxan-3-yl] acetate Chemical compound CC(=O)O[C@@H]1CO[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O MJOQJPYNENPSSS-XQHKEYJVSA-N 0.000 abstract 1
- XXFXTBNFFMQVKJ-UHFFFAOYSA-N [diphenyl(trityloxy)methyl]benzene Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(C=1C=CC=CC=1)OC(C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 XXFXTBNFFMQVKJ-UHFFFAOYSA-N 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 230000008707 rearrangement Effects 0.000 abstract 1
- 230000002194 synthesizing effect Effects 0.000 abstract 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H3/00—Compounds containing only hydrogen atoms and saccharide radicals having only carbon, hydrogen, and oxygen atoms
- C07H3/02—Monosaccharides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Saccharide Compounds (AREA)
Abstract
A method for synthesizing L-ribose (1) and 2-deoxy L-ribose (12) from inexpensive D-ribose (2) is provided. The 5-O-trityl ribose (3) (prepared in 70 % yield from D-ribose) is reduced with borohydride to give the tetrol (4), which is then peracetylated to the tetraacetate (5). Hydrolysis of the trityl ether followed by Swern oxidation affords the aldehyde (7) via the alcohol (6). This aldehyde is a protected form of L-ribose, being L-ribose 2,3,4,5,-tetraacetate. Mild basic hydrolysis of the acetate affords L-ribose itself (1), thus ending an efficient six-step synthesis of (1) from (2) which proceeds in 39 % overall yield. In a second aspect of the invention, L-ribose is converted into the β-selenophenyl ribofuranoside (10) via the tetraester (9) in 71 % isolated yield for the four steps. Treatment of (10) with tributylstannane and AIBN furnishes in 84 % yield the tribenzoyl 2-deoxy-L-ribofuranoside (11) which, on basic hydrolysis, gives 2-deoxy L-ribose (12) in high yield. In a third aspect of the invention, L-arabinose (13) is converted into 2-deoxy L-ribose (12) via the arabinopyranosyl bromide (14), via similar reductive rearrangement with tributylstannane to give the 2-deoxy ribopyranose tribenzoate (16). Hydrolysis yields 2-deoxy L-ribose. In a third aspect of the invention, L-arabinose is converted into 2-deoxy L-ribose by an alternate route.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AU66866/98A AU6686698A (en) | 1997-03-05 | 1998-03-05 | Synthesis of l-ribose and 2-deoxy l-ribose |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US4027097P | 1997-03-05 | 1997-03-05 | |
| US60/040,270 | 1997-03-05 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| WO1998039347A2 WO1998039347A2 (en) | 1998-09-11 |
| WO1998039347A3 true WO1998039347A3 (en) | 1998-10-22 |
Family
ID=21910078
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/US1998/004302 WO1998039347A2 (en) | 1997-03-05 | 1998-03-05 | Synthesis of l-ribose and 2-deoxy l-ribose |
Country Status (2)
| Country | Link |
|---|---|
| AU (1) | AU6686698A (en) |
| WO (1) | WO1998039347A2 (en) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100426030B1 (en) * | 2000-07-22 | 2004-04-03 | (주) 한켐 | Chirality conversion method in lactone sugar compounds |
| KR100440461B1 (en) * | 2000-08-19 | 2004-07-15 | (주) 한켐 | Process for the preparation of L-ribose using 1,4-lactone |
| JP3942414B2 (en) * | 2000-11-29 | 2007-07-11 | 三井化学株式会社 | L-type nucleic acid derivative and synthesis method thereof |
| KR100449310B1 (en) * | 2001-11-08 | 2004-09-18 | 주식회사 삼천리제약 | preparation method of 2-deoxy-L-ribose |
| KR100433179B1 (en) * | 2001-11-10 | 2004-05-27 | 주식회사 삼천리제약 | Method for Producing 2-Deoxy-L-ribose |
| KR100446560B1 (en) * | 2002-07-15 | 2004-09-04 | 주식회사 삼천리제약 | Method for Producing 2-Deoxy-L-ribose |
| KR100849979B1 (en) | 2006-12-06 | 2008-08-01 | 주식회사 삼천리제약 | The preparation method of 2-deoxy-L-ribose |
| CN102108089B (en) * | 2009-12-29 | 2013-10-02 | 唐传生物科技（厦门）有限公司 | Preparation method of 2-deoxy-L-ribose |
| CN102153600B (en) * | 2010-02-12 | 2016-09-14 | 何遂庆 | The preparation method of 2-deoxidation-L-ribose |
| NL2007240C2 (en) * | 2011-08-09 | 2013-02-12 | Konink Co Peratie Cosun U A | Sugar-based plasticizers. |
| CN107778334A (en) * | 2016-08-26 | 2018-03-09 | 康普药业股份有限公司 | A kind of preparation method of Sebivo key intermediate |
-
1998
- 1998-03-05 WO PCT/US1998/004302 patent/WO1998039347A2/en active Application Filing
- 1998-03-05 AU AU66866/98A patent/AU6686698A/en not_active Abandoned
Non-Patent Citations (5)
| Title |
|---|
| CHEMICAL ABSTRACTS, vol. 108, no. 19, 9 May 1988, Columbus, Ohio, US; abstract no. 167793w, R.A.GAKHOKIDZE ET AL.: "Synthesis of 2-Deoxyribose." page 684; column 2; XP002066660 * |
| CHEMICAL ABSTRACTS, vol. 119, no. 25, 20 December 1993, Columbus, Ohio, US; abstract no. 271608c, J.KUBALA ET AL.: "Method of Preparing Optically Active 2-Deoxy-L-Ribose." page 1049; column 1; XP002066659 * |
| CHEMICAL ABSTRACTS, vol. 122, no. 5, 30 January 1995, Columbus, Ohio, US; abstract no. 56398r, J.KUBALA ET AL.: "Process for Preparing L-Ribose." page 1231; column 2; XP002066661 * |
| M.E.JUNG ET AL.: "Efficient Synthesis of L-Ribose and 2-Deoxy-L-Ribose from D-Ribose and L-Arabinose.", TETRAHEDRON LETTERS., vol. 38, no. 24, 1997, OXFORD GB, pages 4199 - 4202, XP004074789 * |
| ZH. ORG. KHIM., vol. 23, no. 5, 1987, pages 1126 - 1127 * |
Also Published As
| Publication number | Publication date |
|---|---|
| AU6686698A (en) | 1998-09-22 |
| WO1998039347A2 (en) | 1998-09-11 |
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