CN108373458A - The synthetic method of the fluoro- 2 methyl-D-ribos-gamma lactones of 3,5- dibenzoyl -2- deoxidations -2- - Google Patents
The synthetic method of the fluoro- 2 methyl-D-ribos-gamma lactones of 3,5- dibenzoyl -2- deoxidations -2- Download PDFInfo
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- CN108373458A CN108373458A CN201711227952.7A CN201711227952A CN108373458A CN 108373458 A CN108373458 A CN 108373458A CN 201711227952 A CN201711227952 A CN 201711227952A CN 108373458 A CN108373458 A CN 108373458A
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- methyl
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/26—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D307/30—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/32—Oxygen atoms
- C07D307/33—Oxygen atoms in position 2, the oxygen atom being in its keto or unsubstituted enol form
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/07—Optical isomers
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- Saccharide Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The present invention relates to the intermediates of Suo Feibuwei synthesis, and in particular to 3,5 dibenzoyls 2 deoxygenate 2 fluorine, 2 methyl D ribose gamma lactones.For the present invention using glucose, N methylbenzylamines, chlorobenzoyl chloride, trifluoromethanesulfanhydride anhydride as primary raw material, 3,5 dibenzoyl 2 of chemical synthesis deoxygenates 2 fluorine, 2 methyl D ribose gamma lactones.Technical solution of the present invention reaction raw materials are cheap and easy to get, intermediate flux important can be reused, into excessively simple re-distillation processing, you can input reaction, it is one of our company major product that intermediate flux ethyl alcohol, acetone, dichloromethane etc., which have recuperability, important source material trifluoromethanesulfonic acid,.Molar yield is improved from original 57% to 73%.
Description
Technical field
The present invention relates to the intermediates of Suo Feibuwei synthesis, and in particular to 3,5- fluoro- 2 first of dibenzoyl -2- deoxidations -2-
Base-D- ribose-gamma lactone.
Background technology
State's hepatitis C neopathy number is just in ascendant trend year by year, and the World Health Organization (WHO) claims, global hepatitis C
For viral (HCV) carrier up to 1.7 hundred million people, this disease leads to every year that there are about 350,000 people death.But hepatitis C (Hepatitis
C) new drug development comes into fast traffic lane.The report issued according to company Datamonitor Healthcare are independently analyzed,
9 years following, the hepatitis C market (Hepatitis C) is estimated by long 230%, and reaches 15,500,000,000 dollars in 2022.Lucky moral
(Gilead) the drug PSI-7977 (Suo Feibuwei) that company receives expectation is somebody's turn to do as the significant contributor in hepatitis C market
Medicine shows gratifying result in clinical test.
The key that the fluoro- 2 methyl-D-ribos-gamma lactones of 3,5- dibenzoyl -2- deoxidations -2- are synthesized as Suo Feibuwei
Intermediate has the great market space and market forces.
Invention content
For the above situation, a kind of cost of present invention offer is less expensive, effectively improves the chemical synthesis 3 of yield, 5- hexichol
The method of the fluoro- 2 methyl-D-ribos-gamma lactones of formoxyl -2- deoxidations -2-.
Using glucose, N- methylbenzylamines, chlorobenzoyl chloride, trifluoromethanesulfanhydride anhydride as primary raw material, specific synthetic technology
Scheme is as follows：
The reached advantageous effect of the present invention is：Reaction raw materials are cheap and easy to get, and intermediate flux important can be reused, into excessively simple
Single re-distillation processing, you can input reaction, intermediate flux ethyl alcohol, acetone, dichloromethane etc. have recuperability, important source material
Trifluoromethanesulfonic acid is one of our company major product.
Furthermore operation process is simple, and the effective optimize technique of the technical solution, production operation process is simple and safe, instead
Mild condition is answered, and is convenient for middle control.
Furthermore the project technique effectively improves yield, and molar yield is improved from original 57% to 73%.And by simple weight
Crystallization processes, you can obtain the sterling of high quality.
Specific implementation mode
Below in conjunction with the embodiment of the present invention, technical scheme of the present invention is clearly and completely described, it is clear that institute
The embodiment of description is only a part of the embodiment of the present invention, instead of all the embodiments.Based on the embodiments of the present invention,
Every other embodiment obtained by those of ordinary skill in the art without making creative efforts, belongs to this hair
The range of bright protection.
Clear, complete description, certainly, described embodiment are carried out to the technical solution in patent of invention example below
The only a part of embodiment of the present invention, instead of all the embodiments.Based on embodiment in the present invention, ordinary skill
Personnel do not make the every other embodiment obtained under the premise of creative work, belong to the scope of the present invention.
The chemical synthesis process of the fluoro- 2 methyl-D-ribos-gamma lactones of 3,5- dibenzoyl -2- deoxidations -2-.
Using glucose, N- methylbenzylamines, chlorobenzoyl chloride, trifluoromethanesulfanhydride anhydride as primary raw material, specific synthetic technology
Scheme is as follows：
Molar yield is improved from original 57% to 73%.
It although an embodiment of the present invention has been shown and described, for the ordinary skill in the art, can be with
Understanding without departing from the principles and spirit of the present invention can carry out these embodiments a variety of variations, modification, replace
And modification, the scope of the present invention is defined by the appended.
Claims (1)
1. one kind 3, the synthetic method of the fluoro- 2 methyl-D-ribos-gamma lactones of 5- dibenzoyl -2- deoxidations -2-, feature exist
In using glucose, N- methylbenzylamines, chlorobenzoyl chloride, trifluoromethanesulfanhydride anhydride as primary raw material, specific synthetic technology scheme is such as
Under：
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201711227952.7A CN108373458A (en) | 2017-11-29 | 2017-11-29 | The synthetic method of the fluoro- 2 methyl-D-ribos-gamma lactones of 3,5- dibenzoyl -2- deoxidations -2- |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201711227952.7A CN108373458A (en) | 2017-11-29 | 2017-11-29 | The synthetic method of the fluoro- 2 methyl-D-ribos-gamma lactones of 3,5- dibenzoyl -2- deoxidations -2- |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN108373458A true CN108373458A (en) | 2018-08-07 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201711227952.7A Pending CN108373458A (en) | 2017-11-29 | 2017-11-29 | The synthetic method of the fluoro- 2 methyl-D-ribos-gamma lactones of 3,5- dibenzoyl -2- deoxidations -2- |
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| CN (1) | CN108373458A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112430224A (en) * | 2020-11-17 | 2021-03-02 | 江西国化实业有限公司 | Preparation process of 5-dibenzoyl-2-deoxy-2-fluoro-2 methyl-D-ribose-r-lactone |
| CN115448896A (en) * | 2022-10-24 | 2022-12-09 | 江苏阿尔法药业股份有限公司 | Preparation method of sofosbuvir intermediate |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105693661A (en) * | 2014-12-15 | 2016-06-22 | 苏州旺山旺水生物医药有限公司 | Preparation method and intermediate body of (2S, 3R, 4R)-3,5-bis-sustituted-2-deoxy-2-hydroxy-2-methyl-D-ribose-gamma-lactone |
-
2017
- 2017-11-29 CN CN201711227952.7A patent/CN108373458A/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105693661A (en) * | 2014-12-15 | 2016-06-22 | 苏州旺山旺水生物医药有限公司 | Preparation method and intermediate body of (2S, 3R, 4R)-3,5-bis-sustituted-2-deoxy-2-hydroxy-2-methyl-D-ribose-gamma-lactone |
Non-Patent Citations (2)
| Title |
|---|
| DAVID J. HOTCHKISS，等: "Amadori ketoses with calcium hydroxide and the Kiliani reaction on 1-deoxy ketoses: two approaches to the synthesis of saccharinic acids", 《TETRAHEDRON LETTERS》 * |
| YUANCHAO XIE，等: "A neighboring group participation strategy: facile synthesis of 3,5-di-O-benzoyl-2-C-methyl-D-arabino-r-lactone", 《TETRAHEDRON LETTERS》 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112430224A (en) * | 2020-11-17 | 2021-03-02 | 江西国化实业有限公司 | Preparation process of 5-dibenzoyl-2-deoxy-2-fluoro-2 methyl-D-ribose-r-lactone |
| CN115448896A (en) * | 2022-10-24 | 2022-12-09 | 江苏阿尔法药业股份有限公司 | Preparation method of sofosbuvir intermediate |
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| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| RJ01 | Rejection of invention patent application after publication |
Application publication date: 20180807 |
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| RJ01 | Rejection of invention patent application after publication |