(R)-3-(tert-Butyl-dimethyl-silanyloxy)-4-[(2S,3S)-3-(toluene-4-sulfonyloxymethyl)-oxiranyl]-butyric acid methyl ester

Base Information

Chemical Name:(R)-3-(tert-Butyl-dimethyl-silanyloxy)-4-[(2S,3S)-3-(toluene-4-sulfonyloxymethyl)-oxiranyl]-butyric acid methyl ester
CAS No.:159787-31-2
Molecular Formula:C₂₁H₃₄O₇SSi
Molecular Weight:458.648
Hs Code.:

Synonyms:(R)-3-(tert-Butyl-dimethyl-silanyloxy)-4-[(2S,3S)-3-(toluene-4-sulfonyloxymethyl)-oxiranyl]-butyric acid methyl ester

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Chemical Property of (R)-3-(tert-Butyl-dimethyl-silanyloxy)-4-[(2S,3S)-3-(toluene-4-sulfonyloxymethyl)-oxiranyl]-butyric acid methyl ester

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Technology Process of (R)-3-(tert-Butyl-dimethyl-silanyloxy)-4-[(2S,3S)-3-(toluene-4-sulfonyloxymethyl)-oxiranyl]-butyric acid methyl ester

There total 7 articles about (R)-3-(tert-Butyl-dimethyl-silanyloxy)-4-[(2S,3S)-3-(toluene-4-sulfonyloxymethyl)-oxiranyl]-butyric 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: 75.0%

: 98-59-9
p-toluenesulfonyl chloride

: 159787-29-8
(2S,3S,βR)-3-<(tert-butyldimethylsilyl)oxy>-3-<(methoxycarbonyl)propyl>oxiranemethanol

: 159787-31-2
(R)-3-(tert-Butyl-dimethyl-silanyloxy)-4-[(2S,3S)-3-(toluene-4-sulfonyloxymethyl)-oxiranyl]-butyric acid methyl ester

Guidance literature:: With dmap; triethylamine; In dichloromethane; Ambient temperature;
DOI:10.1021/jo00096a017

Reference yield:

: 121980-45-8
(3R)-(-)-methyl 3-<(tert-butyldimethylsilyl)oxy>-4-formylbutanoate

: 159787-31-2
(R)-3-(tert-Butyl-dimethyl-silanyloxy)-4-[(2S,3S)-3-(toluene-4-sulfonyloxymethyl)-oxiranyl]-butyric acid methyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 67 percent / benzene; tetrahydrofuran / Heating

2: 78 percent / NaBH₄ / methanol / -50 °C

3: 40 percent / t-BuO₂H, Ti(Oi-Pr)4 / (+)-DIPT

4: 75 percent / Et₃N, DMAP / CH₂Cl₂ / Ambient temperature

With titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; sodium tetrahydroborate; triethylamine; L-(+)-diisopropyl tartrate; In tetrahydrofuran; methanol; dichloromethane; benzene;
DOI:10.1021/jo00096a017

Reference yield:

: 80959-53-1
3-hydroxypent-4-enoic acid methyl ester

: 159787-31-2
(R)-3-(tert-Butyl-dimethyl-silanyloxy)-4-[(2S,3S)-3-(toluene-4-sulfonyloxymethyl)-oxiranyl]-butyric acid methyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: imidazole / dimethylformamide

2: 1.) (Me₂CHCHMe)2BH, 2.) PCC / 1.) THF, -12 deg C, 2.) CH₂Cl₂, reflux

3: 67 percent / benzene; tetrahydrofuran / Heating

4: 78 percent / NaBH₄ / methanol / -50 °C

5: 40 percent / t-BuO₂H, Ti(Oi-Pr)4 / (+)-DIPT

6: 75 percent / Et₃N, DMAP / CH₂Cl₂ / Ambient temperature

With 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; sodium tetrahydroborate; bis-(1,2-dimethylpropyl)borane; triethylamine; pyridinium chlorochromate; L-(+)-diisopropyl tartrate; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; benzene;
DOI:10.1021/jo00096a017