(1S,2S,3R,4S)-1-(tert-Butyl-dimethyl-silanyloxy)-2,4-bis-(tert-butyl-dimethyl-silanyloxymethyl)-1-{(2S,3R)-3-[(S)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-2-methyl-oxiranyl}-hex-5-en-3-ol

Base Information

Chemical Name:(1S,2S,3R,4S)-1-(tert-Butyl-dimethyl-silanyloxy)-2,4-bis-(tert-butyl-dimethyl-silanyloxymethyl)-1-{(2S,3R)-3-[(S)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-2-methyl-oxiranyl}-hex-5-en-3-ol
CAS No.:651355-72-5
Molecular Formula:C₄₀H₇₆O₇Si₃
Molecular Weight:753.296
Hs Code.:

(1S,2S,3R,4S)-1-(tert-Butyl-dimethyl-silanyloxy)-2,4-bis-(tert-butyl-dimethyl-silanyloxymethyl)-1-{(2S,3R)-3-[(S)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-2-methyl-oxiranyl}-hex-5-en-3-ol

Synonyms:(1S,2S,3R,4S)-1-(tert-Butyl-dimethyl-silanyloxy)-2,4-bis-(tert-butyl-dimethyl-silanyloxymethyl)-1-{(2S,3R)-3-[(S)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-2-methyl-oxiranyl}-hex-5-en-3-ol

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Chemical Property of (1S,2S,3R,4S)-1-(tert-Butyl-dimethyl-silanyloxy)-2,4-bis-(tert-butyl-dimethyl-silanyloxymethyl)-1-{(2S,3R)-3-[(S)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-2-methyl-oxiranyl}-hex-5-en-3-ol

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Technology Process of (1S,2S,3R,4S)-1-(tert-Butyl-dimethyl-silanyloxy)-2,4-bis-(tert-butyl-dimethyl-silanyloxymethyl)-1-{(2S,3R)-3-[(S)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-2-methyl-oxiranyl}-hex-5-en-3-ol

There total 6 articles about (1S,2S,3R,4S)-1-(tert-Butyl-dimethyl-silanyloxy)-2,4-bis-(tert-butyl-dimethyl-silanyloxymethyl)-1-{(2S,3R)-3-[(S)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-2-methyl-oxiranyl}-hex-5-en-3-ol 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: 97.0%

: 18162-48-6
tert-butyldimethylsilyl chloride

: 651355-71-4
(2S,3R,4S,5S)-5-(tert-Butyl-dimethyl-silanyloxy)-4-(tert-butyl-dimethyl-silanyloxymethyl)-5-{(2S,3R)-3-[(S)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-2-methyl-oxiranyl}-2-vinyl-pentane-1,3-diol

: 651355-72-5
(1S,2S,3R,4S)-1-(tert-Butyl-dimethyl-silanyloxy)-2,4-bis-(tert-butyl-dimethyl-silanyloxymethyl)-1-{(2S,3R)-3-[(S)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-2-methyl-oxiranyl}-hex-5-en-3-ol

Guidance literature:: With 1H-imidazole; In dichloromethane; at 23 ℃; for 4h;

Reference yield:

: 18162-48-6
tert-butyldimethylsilyl chloride

: 651355-72-5
(1S,2S,3R,4S)-1-(tert-Butyl-dimethyl-silanyloxy)-2,4-bis-(tert-butyl-dimethyl-silanyloxymethyl)-1-{(2S,3R)-3-[(S)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-2-methyl-oxiranyl}-hex-5-en-3-ol

Guidance literature:: Multi-step reaction with 5 steps

1.1: 90 percent / imidazole / CH₂Cl₂ / 23 °C

2.1: 70 percent / O₃; PPh₃ / CH₂Cl₂ / -78 °C

3.1: Bu₂BOTf; Et₃N / CH₂Cl₂ / -78 °C

3.2: 90 percent / CH₂Cl₂ / -30 °C

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

4.2: 95 percent / H₂O₂ / diethyl ether / 0 °C

5.1: 92 percent / imidazole / CH₂Cl₂ / 23 °C

With 1H-imidazole; lithium borohydride; di-n-butylboryl trifluoromethanesulfonate; ozone; triethylamine; triphenylphosphine; In tetrahydrofuran; dichloromethane; water;
DOI:10.1002/anie.200353313

Reference yield:

: 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

: 651355-72-5
(1S,2S,3R,4S)-1-(tert-Butyl-dimethyl-silanyloxy)-2,4-bis-(tert-butyl-dimethyl-silanyloxymethyl)-1-{(2S,3R)-3-[(S)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-2-methyl-oxiranyl}-hex-5-en-3-ol

Guidance literature:: Multi-step reaction with 5 steps

1.1: 90 percent / imidazole / CH₂Cl₂ / 23 °C

2.1: 70 percent / O₃; PPh₃ / CH₂Cl₂ / -78 °C

3.1: Bu₂BOTf; Et₃N / CH₂Cl₂ / -78 °C

3.2: 90 percent / CH₂Cl₂ / -30 °C

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

4.2: 95 percent / H₂O₂ / diethyl ether / 0 °C

5.1: 92 percent / imidazole / CH₂Cl₂ / 23 °C

With 1H-imidazole; lithium borohydride; di-n-butylboryl trifluoromethanesulfonate; ozone; triethylamine; triphenylphosphine; In tetrahydrofuran; dichloromethane; water;
DOI:10.1002/anie.200353313