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US4384998A
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Synthesis of thienamycin from D-glucose
Assignee: Merck and Co Inc
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Filing: 1981-03-30
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Granted: 1983-05-24
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Expires: 2001-03-30
Abstract
Abstract Disclosed is a chiral, total synthesis of thienamycin from D-glucose which proceeds via intermediates I, II and III to known aldehyde IV which is known to be useful in the total synthesis of thienamycin (V): ##STR1## wherein: R is lower alkyl having 1-6 carbon atoms or bi-valent alkyl having 2-6 carbon atoms which joins the two sulfur atoms; R 1 is lower alkyl or aralkyl, such as benzyl and the like; and R 2 is hydrogen or a removable protecting group, such as triorganosilyl wherein the organo groups are independently selected from lower alkyl, phenyl and phenylloweralkyl.
Inventors
- 👤 Philippe L. Durette
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-04 06:42
CPC Classifications
C; C07; C07H; C07H19/00; C07H19/02; C07H19/04; C07D; C07D205/00; C07D205/02; C07D205/06; C07D205/08; C07D477/00; C07D477/02; C07D477/04; C07H9/00; Y; Y02; Y02P; Y02P20/00; Y02P20/50; Y02P20/55
Claims Analysis
Total Claims: 3
Claim 1
Independent Claim
159 words
A process for preparing: ##STR14## comprising the steps of: treating: ##STR15## with mineral acid and an alkanethiol, a phenylalkanethiol, or a alkanedithiol to yield: ##STR16## followed by alcoholysis with the alcohol R 1 OH to yield ##STR17## wherein R 1 is alkyl having 1-6 carbon atoms; followed by treating with hydrogen and a hydrogenation catalyst to yield: ##STR18## followed by treating with a triorganosilyl chloride and cyclization in the presence of a Grignard reagent selected from ethylmagnesiumbromide, methyl magnesiumiodide and t-butylmagnesiumchloride, to yield ##STR19## followed by treating in a solvent selected from aqueous tetrahydrofuran, aqueous acetone, aqueous acetonitrite and aqueous p-dioxane with a Lewis acid selected from mercuric oxide, mercuric chloride, boron trifluoride etherate, thallium trinitrate and silver tetrafluorobovate wherein R 4 and R 5 are independently selected from alkyl having 1-6 carbon atoms, phenylalkyl; or wherein the SR 4 and SR 5 groups taken together with the carbon atom to which they are attached form a dithiacycloalkyl group.
Claim 2
Dependent Claim
159 words
A process for preparing: ##STR14## comprising the steps of: treating: ##STR15## with mineral acid and an alkanethiol, a phenylalkanethiol, or a alkanedithiol to yield: ##STR16## followed by alcoholysis with the alcohol R 1 OH to yield ##STR17## wherein R 1 is alkyl having 1-6 carbon atoms; followed by treating with hydrogen and a hydrogenation catalyst to yield: ##STR18## followed by treating with a triorganosilyl chloride and cyclization in the presence of a Grignard reagent selected from ethylmagnesiumbromide, methyl magnesiumiodide and t-butylmagnesiumchloride, to yield ##STR19## followed by treating in a solvent selected from aqueous tetrahydrofuran, aqueous acetone, aqueous acetonitrite and aqueous p-dioxane with a Lewis acid selected from mercuric oxide, mercuric chloride, boron trifluoride etherate, thallium trinitrate and silver tetrafluorobovate wherein R 4 and R 5 are independently selected from alkyl having 1-6 carbon atoms, phenylalkyl; or wherein the SR 4 and SR 5 groups taken together with the carbon atom to which they are attached form a dithiacycloalkyl group.
Claim 3
Dependent Claim
21 words
A process according to claim 1, wherein SR 4 and SR 5 are joined to form --S--(CH 2 ) 3 --S--.
References Cited (Backward Citations)
US4234596A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1986-05-23 | 1986-11-22 | 1987-05-24 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1990-05-23 | 1990-11-22 | 1991-05-24 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1994-05-23 | 1994-11-22 | 1995-05-24 | $7700.00 | Window Closed / Lapsed |