(3S,4R,5R)-4-Acetoxy-5-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-cyclohex-1-enecarboxylic acid methyl ester

Base Information

Chemical Name:(3S,4R,5R)-4-Acetoxy-5-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-cyclohex-1-enecarboxylic acid methyl ester
CAS No.:88424-81-1
Molecular Formula:C₁₆H₂₈O₆Si
Molecular Weight:344.48
Hs Code.:

Synonyms:(3S,4R,5R)-4-Acetoxy-5-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-cyclohex-1-enecarboxylic acid methyl ester

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Chemical Property of (3S,4R,5R)-4-Acetoxy-5-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-cyclohex-1-enecarboxylic acid methyl ester

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Technology Process of (3S,4R,5R)-4-Acetoxy-5-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-cyclohex-1-enecarboxylic acid methyl ester

There total 24 articles about (3S,4R,5R)-4-Acetoxy-5-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-cyclohex-1-enecarboxylic acid methyl ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

: 138-59-0
shikimic acid

: 88424-81-1
(3S,4R,5R)-4-Acetoxy-5-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-cyclohex-1-enecarboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 99 percent / methanol; diethyl ether / 15 h / Ambient temperature

2: 90 percent / p-toluenesulfonic acid, Na₂CO₃ / CH₂Cl₂ / 5 °C

3: imidazole / dimethylformamide / 1.75 h

4: 1.) H₂O, AcOH; 2) pyridinium dichromate / 1.) methanol, toluene r.t., 1 h; 2.) DMF, 45 deg C, 1 h

6: sodium borohydride / ethanol / 5 °C

With 1H-imidazole; sodium tetrahydroborate; dipyridinium dichromate; water; sodium carbonate; toluene-4-sulfonic acid; acetic acid; In methanol; diethyl ether; ethanol; dichloromethane; N,N-dimethyl-formamide;

Reference yield:

: 40983-58-2
methyl shikimate

: 88424-81-1
(3S,4R,5R)-4-Acetoxy-5-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-cyclohex-1-enecarboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 90 percent / p-toluenesulfonic acid, Na₂CO₃ / CH₂Cl₂ / 5 °C

2: imidazole / dimethylformamide / 1.75 h

3: 1.) H₂O, AcOH; 2) pyridinium dichromate / 1.) methanol, toluene r.t., 1 h; 2.) DMF, 45 deg C, 1 h

5: sodium borohydride / ethanol / 5 °C

With 1H-imidazole; sodium tetrahydroborate; dipyridinium dichromate; water; sodium carbonate; toluene-4-sulfonic acid; acetic acid; In ethanol; dichloromethane; N,N-dimethyl-formamide;

Reference yield:

: 88400-31-1
(3aR,7R,7aS)-7-Hydroxy-2-methoxy-2-methyl-3a,6,7,7a-tetrahydro-benzo[1,3]dioxole-5-carboxylic acid methyl ester

: 88424-81-1
(3S,4R,5R)-4-Acetoxy-5-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-cyclohex-1-enecarboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: imidazole / dimethylformamide / 1.75 h

2: 1.) H₂O, AcOH; 2) pyridinium dichromate / 1.) methanol, toluene r.t., 1 h; 2.) DMF, 45 deg C, 1 h

4: sodium borohydride / ethanol / 5 °C

With 1H-imidazole; sodium tetrahydroborate; dipyridinium dichromate; water; acetic acid; In ethanol; N,N-dimethyl-formamide;