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

Base Information

Chemical Name:(2S,3S,4S,5S)-5-(tert-Butyl-dimethyl-silanyloxy)-2,4-bis-(tert-butyl-dimethyl-silanyloxymethyl)-3-hydroxy-5-{(2S,3R)-3-[(S)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-2-methyl-oxiranyl}-pentanal
CAS No.:651355-73-6
Molecular Formula:C₃₉H₇₄O₈Si₃
Molecular Weight:755.268
Hs Code.:

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

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

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

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

There total 7 articles about (2S,3S,4S,5S)-5-(tert-Butyl-dimethyl-silanyloxy)-2,4-bis-(tert-butyl-dimethyl-silanyloxymethyl)-3-hydroxy-5-{(2S,3R)-3-[(S)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-2-methyl-oxiranyl}-pentanal 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: 84.0%

: 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

: 651355-73-6
(2S,3S,4S,5S)-5-(tert-Butyl-dimethyl-silanyloxy)-2,4-bis-(tert-butyl-dimethyl-silanyloxymethyl)-3-hydroxy-5-{(2S,3R)-3-[(S)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-2-methyl-oxiranyl}-pentanal

Guidance literature:: (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; With ozone; In dichloromethane; at -78 ℃; for 0.25h;

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

Reference yield:

: 18162-48-6
tert-butyldimethylsilyl chloride

: 651355-73-6
(2S,3S,4S,5S)-5-(tert-Butyl-dimethyl-silanyloxy)-2,4-bis-(tert-butyl-dimethyl-silanyloxymethyl)-3-hydroxy-5-{(2S,3R)-3-[(S)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-2-methyl-oxiranyl}-pentanal

Guidance literature:: Multi-step reaction with 6 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

6.1: 82 percent / O₃; PPh₃ / CH₂Cl₂ / -78 °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

: 651355-73-6
(2S,3S,4S,5S)-5-(tert-Butyl-dimethyl-silanyloxy)-2,4-bis-(tert-butyl-dimethyl-silanyloxymethyl)-3-hydroxy-5-{(2S,3R)-3-[(S)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-2-methyl-oxiranyl}-pentanal

Guidance literature:: Multi-step reaction with 6 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

6.1: 82 percent / O₃; PPh₃ / CH₂Cl₂ / -78 °C

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