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

Base Information

Chemical Name:(3R,4R,5R)-3,4-Diacetoxy-5-(tert-butyl-dimethyl-silanyloxy)-cyclohex-1-enecarboxylic acid methyl ester
CAS No.:88400-36-6
Molecular Formula:C₁₈H₃₀O₇Si
Molecular Weight:386.518
Hs Code.:

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

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

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

There total 12 articles about (3R,4R,5R)-3,4-Diacetoxy-5-(tert-butyl-dimethyl-silanyloxy)-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:

: 40983-58-2
methyl shikimate

: 88400-36-6
(3R,4R,5R)-3,4-Diacetoxy-5-(tert-butyl-dimethyl-silanyloxy)-cyclohex-1-enecarboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 3 steps

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

2: imidazole / dimethylformamide / 1.75 h

3: 1.) H₂O, AcOH; 2.) N,N-dimethylolpyridine / 1.) methanol, toluene, r.t., 1 h; 2) ether, 1 h

With 1H-imidazole; N,N-dimethylolpyridine; water; sodium carbonate; toluene-4-sulfonic acid; acetic acid; In 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

: 88400-36-6
(3R,4R,5R)-3,4-Diacetoxy-5-(tert-butyl-dimethyl-silanyloxy)-cyclohex-1-enecarboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: imidazole / dimethylformamide / 1.75 h

2: 1.) H₂O, AcOH; 2.) N,N-dimethylolpyridine / 1.) methanol, toluene, r.t., 1 h; 2) ether, 1 h

With 1H-imidazole; N,N-dimethylolpyridine; water; acetic acid; In N,N-dimethyl-formamide;

Reference yield:

: 88400-32-2
(3aR,7R,7aR)-7-(tert-Butyl-dimethyl-silanyloxy)-2-methoxy-2-methyl-3a,6,7,7a-tetrahydro-benzo[1,3]dioxole-5-carboxylic acid methyl ester

: 88400-36-6
(3R,4R,5R)-3,4-Diacetoxy-5-(tert-butyl-dimethyl-silanyloxy)-cyclohex-1-enecarboxylic acid methyl ester

Guidance literature:: With water; hydrogenchloride; Yield given. Multistep reaction; 1.) methanol, room temp., 1h; 2.) re-acetylation;
DOI:10.1016/S0040-4039(00)85910-9