(2S,3R)-2-[(1S,2R)-1-(tert-Butyl-dimethyl-silanyloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-but-3-enyl]-3-[(S)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-2-methyl-oxirane

Base Information

Chemical Name:(2S,3R)-2-[(1S,2R)-1-(tert-Butyl-dimethyl-silanyloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-but-3-enyl]-3-[(S)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-2-methyl-oxirane
CAS No.:651355-67-8
Molecular Formula:C₃₁H₅₆O₅Si₂
Molecular Weight:564.954
Hs Code.:

(2S,3R)-2-[(1S,2R)-1-(tert-Butyl-dimethyl-silanyloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-but-3-enyl]-3-[(S)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-2-methyl-oxirane

Synonyms:(2S,3R)-2-[(1S,2R)-1-(tert-Butyl-dimethyl-silanyloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-but-3-enyl]-3-[(S)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-2-methyl-oxirane

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Chemical Property of (2S,3R)-2-[(1S,2R)-1-(tert-Butyl-dimethyl-silanyloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-but-3-enyl]-3-[(S)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-2-methyl-oxirane

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Technology Process of (2S,3R)-2-[(1S,2R)-1-(tert-Butyl-dimethyl-silanyloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-but-3-enyl]-3-[(S)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-2-methyl-oxirane

There total 1 articles about (2S,3R)-2-[(1S,2R)-1-(tert-Butyl-dimethyl-silanyloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-but-3-enyl]-3-[(S)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-2-methyl-oxirane 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: 90.0%

: 18162-48-6
tert-butyldimethylsilyl chloride

: 236117-59-2
(R)-2-((S)-(tert-Butyl-dimethyl-silanyloxy)-{(2S,3R)-3-[(S)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-2-methyl-oxiranyl}-methyl)-but-3-en-1-ol

: 651355-67-8
(2S,3R)-2-[(1S,2R)-1-(tert-Butyl-dimethyl-silanyloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-but-3-enyl]-3-[(S)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-2-methyl-oxirane

Guidance literature:: With 1H-imidazole; In dichloromethane; at 23 ℃;
DOI:10.1002/anie.200353313

Reference yield: 72.0%

: 651355-67-8
(2S,3R)-2-[(1S,2R)-1-(tert-Butyl-dimethyl-silanyloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-but-3-enyl]-3-[(S)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-2-methyl-oxirane

: 651355-69-0
(2R,3S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-3-{(2S,3R)-3-[(S)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-2-methyl-oxiranyl}-propionaldehyde

Guidance literature:: (2S,3R)-2-[(1S,2R)-1-(tert-Butyl-dimethyl-silanyloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-but-3-enyl]-3-[(S)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-2-methyl-oxirane; With ozone; In dichloromethane; at -78 ℃; for 0.833333h;

With triphenylphosphine; In dichloromethane; at 20 ℃; for 12h;

Reference yield:

: 651355-67-8
(2S,3R)-2-[(1S,2R)-1-(tert-Butyl-dimethyl-silanyloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-but-3-enyl]-3-[(S)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-2-methyl-oxirane

: 651355-74-7
(3S,4R,5R,6S,7S)-7-(tert-Butyl-dimethyl-silanyloxy)-4,6-bis-(tert-butyl-dimethyl-silanyloxymethyl)-3,5-dihydroxy-7-{(2S,3R)-3-[(S)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-2-methyl-oxiranyl}-heptanoic acid methoxy-methyl-amide

Guidance literature:: Multi-step reaction with 8 steps

1.1: 70 percent / O₃; PPh₃ / CH₂Cl₂ / -78 °C

2.1: Bu₂BOTf; Et₃N / CH₂Cl₂ / -78 °C

2.2: 90 percent / CH₂Cl₂ / -30 °C

3.1: LiBH₄ / tetrahydrofuran; H₂O / 0 - 23 °C

3.2: 95 percent / H₂O₂ / diethyl ether / 0 °C

4.1: 92 percent / imidazole / CH₂Cl₂ / 23 °C

5.1: 82 percent / O₃; PPh₃ / CH₂Cl₂ / -78 °C

6.1: LDA / tetrahydrofuran / -78 °C

7.1: Dess-Martin reagent

8.1: NaBH₄ / methanol

With 1H-imidazole; sodium tetrahydroborate; lithium borohydride; di-n-butylboryl trifluoromethanesulfonate; Dess-Martin periodane; ozone; triethylamine; triphenylphosphine; lithium diisopropyl amide; In tetrahydrofuran; methanol; dichloromethane; water; 6.1: aldol reaction;
DOI:10.1002/anie.200353313