(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

Base Information

Chemical Name:(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
CAS No.:651355-71-4
Molecular Formula:C₃₄H₆₂O₇Si₂
Molecular Weight:639.033
Hs Code.:

(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

Synonyms:(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

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Chemical Property of (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

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Technology Process of (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

There total 5 articles about (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 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: 95.0%

: 651355-70-3
(R)-3-((2R,3S,4S,5S)-5-(tert-Butyl-dimethyl-silanyloxy)-4-(tert-butyl-dimethyl-silanyloxymethyl)-3-hydroxy-5-{(2S,3R)-3-[(S)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-2-methyl-oxiranyl}-2-vinyl-pentanoyl)-4-isopropyl-oxazolidin-2-one

: 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

Guidance literature:: (R)-3-((2R,3S,4S,5S)-5-(tert-Butyl-dimethyl-silanyloxy)-4-(tert-butyl-dimethyl-silanyloxymethyl)-3-hydroxy-5-{(2S,3R)-3-[(S)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-2-methyl-oxiranyl}-2-vinyl-pentanoyl)-4-isopropyl-oxazolidin-2-one; With lithium borohydride; In tetrahydrofuran; water; at 0 - 23 ℃;

With dihydrogen peroxide; In diethyl ether; at 0 ℃;
DOI:10.1002/anie.200353313

Reference yield:

: 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

Guidance literature:: Multi-step reaction with 4 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

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

: 651355-71-4
(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

Guidance literature:: Multi-step reaction with 4 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

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