(3S,4R,5R)-5-{[(tert-butyl)dimethylsilyl]oxy}-3-hydroxy-4-methoxycyclohex-1-ene-1-carboxylic acid methyl ester

Base Information

Chemical Name:(3S,4R,5R)-5-{[(tert-butyl)dimethylsilyl]oxy}-3-hydroxy-4-methoxycyclohex-1-ene-1-carboxylic acid methyl ester
CAS No.:950897-47-9
Molecular Formula:C₁₅H₂₈O₅Si
Molecular Weight:316.47
Hs Code.:

Synonyms:(3S,4R,5R)-5-{[(tert-butyl)dimethylsilyl]oxy}-3-hydroxy-4-methoxycyclohex-1-ene-1-carboxylic acid methyl ester

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Chemical Property of (3S,4R,5R)-5-{[(tert-butyl)dimethylsilyl]oxy}-3-hydroxy-4-methoxycyclohex-1-ene-1-carboxylic acid methyl ester

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Technology Process of (3S,4R,5R)-5-{[(tert-butyl)dimethylsilyl]oxy}-3-hydroxy-4-methoxycyclohex-1-ene-1-carboxylic acid methyl ester

There total 8 articles about (3S,4R,5R)-5-{[(tert-butyl)dimethylsilyl]oxy}-3-hydroxy-4-methoxycyclohex-1-ene-1-carboxylic 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: 85.0%

: 185810-88-2
(4S,5R)-5-{[(tert-butyl)dimethylsilyl]oxy}-4-methoxy-3-oxocyclohex-1-ene-1-carboxylic acid methyl ester

: 950897-47-9
(3S,4R,5R)-5-{[(tert-butyl)dimethylsilyl]oxy}-3-hydroxy-4-methoxycyclohex-1-ene-1-carboxylic acid methyl ester

Guidance literature:: With sodium tetrahydroborate; cerium(III) chloride; In methanol; at -20 ℃; for 0.5h;
DOI:10.1002/hlca.200790138

Reference yield: 20.0%

: 108-05-4,9003-20-7
vinyl acetate

: methyl (3R*,4S*,5S*)-5-(tert-butyldimethyl)silyloxy-3-hydroxy-4-methoxy-1-cyclohexenecarboxylate

: 950897-47-9
(3S,4R,5R)-5-{[(tert-butyl)dimethylsilyl]oxy}-3-hydroxy-4-methoxycyclohex-1-ene-1-carboxylic acid methyl ester

: methyl (3R,4S,5S)-5-(tert-butyldimethyl)silyloxy-3-hydroxy-4-methoxy-1-cyclohexenecarboxylate

: 1257516-64-5
C₁₇H₃₀O₆Si

: C₁₇H₃₀O₆Si

Guidance literature:: With Candida antarctica lipase B (Novozym 435); at 30 ℃; for 24h; optical yield given as %ee; enantioselective reaction; Resolution of racemate; Enzymatic reaction;
DOI:10.1016/j.molcatb.2010.07.009

Reference yield:

: 950897-45-7
(3R,4S,5R)-3,5-bis{[(tert-butyl)dimethylsilyl]oxy}-4-methoxycyclohex-1-ene-1-carboxylic acid methyl ester

: 950897-47-9
(3S,4R,5R)-5-{[(tert-butyl)dimethylsilyl]oxy}-3-hydroxy-4-methoxycyclohex-1-ene-1-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 90 percent / AcOH; water / tetrahydrofuran / 36 h / 40 °C

2: 85 percent / pyridinium dichromate / dimethylformamide / 2 h / 15 °C

3: 90 percent / 1H-imidazole; DMAP / dimethylformamide / 12 h / 0 °C

4: 85 percent / CeCl₃*7H₂O; NaBH₄ / methanol / 0.5 h / -20 °C

With 1H-imidazole; dmap; sodium tetrahydroborate; dipyridinium dichromate; cerium(III) chloride; water; acetic acid; In tetrahydrofuran; methanol; N,N-dimethyl-formamide;
DOI:10.1002/hlca.200790138