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

Base Information

Chemical Name:(3S,4S,5R,6S,7S)-3,7-Bis-(tert-butyl-dimethyl-silanyloxy)-4,6-bis-(tert-butyl-dimethyl-silanyloxymethyl)-5-hydroxy-7-{(2S,3R)-3-[(S)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-2-methyl-oxiranyl}-heptanoic acid methoxy-methyl-amide
CAS No.:651355-76-9
Molecular Formula:C₄₉H₉₇NO₁₀Si₄
Molecular Weight:972.652
Hs Code.:

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

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

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Chemical Property of (3S,4S,5R,6S,7S)-3,7-Bis-(tert-butyl-dimethyl-silanyloxy)-4,6-bis-(tert-butyl-dimethyl-silanyloxymethyl)-5-hydroxy-7-{(2S,3R)-3-[(S)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-2-methyl-oxiranyl}-heptanoic acid methoxy-methyl-amide

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Technology Process of (3S,4S,5R,6S,7S)-3,7-Bis-(tert-butyl-dimethyl-silanyloxy)-4,6-bis-(tert-butyl-dimethyl-silanyloxymethyl)-5-hydroxy-7-{(2S,3R)-3-[(S)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-2-methyl-oxiranyl}-heptanoic acid methoxy-methyl-amide

There total 11 articles about (3S,4S,5R,6S,7S)-3,7-Bis-(tert-butyl-dimethyl-silanyloxy)-4,6-bis-(tert-butyl-dimethyl-silanyloxymethyl)-5-hydroxy-7-{(2S,3R)-3-[(S)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-2-methyl-oxiranyl}-heptanoic acid methoxy-methyl-amide 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: 81.0%

: 69739-34-0
t-butyldimethylsiyl triflate

: 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

: 651355-76-9
(3S,4S,5R,6S,7S)-3,7-Bis-(tert-butyl-dimethyl-silanyloxy)-4,6-bis-(tert-butyl-dimethyl-silanyloxymethyl)-5-hydroxy-7-{(2S,3R)-3-[(S)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-2-methyl-oxiranyl}-heptanoic acid methoxy-methyl-amide

Guidance literature:: With 2,6-dimethylpyridine; In dichloromethane; at 0 ℃;
DOI:10.1002/anie.200353313

Reference yield:

: 18162-48-6
tert-butyldimethylsilyl chloride

: 651355-76-9
(3S,4S,5R,6S,7S)-3,7-Bis-(tert-butyl-dimethyl-silanyloxy)-4,6-bis-(tert-butyl-dimethyl-silanyloxymethyl)-5-hydroxy-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 10 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

7.1: LDA / tetrahydrofuran / -78 °C

8.1: Dess-Martin reagent

9.1: NaBH₄ / methanol

10.1: 81 percent / 2,6-lutidine / CH₂Cl₂ / 0 °C

With 1H-imidazole; 2,6-dimethylpyridine; sodium tetrahydroborate; lithium borohydride; di-n-butylboryl trifluoromethanesulfonate; Dess-Martin periodane; ozone; triethylamine; triphenylphosphine; lithium diisopropyl amide; In tetrahydrofuran; methanol; dichloromethane; water; 7.1: aldol reaction;
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

: 651355-76-9
(3S,4S,5R,6S,7S)-3,7-Bis-(tert-butyl-dimethyl-silanyloxy)-4,6-bis-(tert-butyl-dimethyl-silanyloxymethyl)-5-hydroxy-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 10 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

7.1: LDA / tetrahydrofuran / -78 °C

8.1: Dess-Martin reagent

9.1: NaBH₄ / methanol

10.1: 81 percent / 2,6-lutidine / CH₂Cl₂ / 0 °C

With 1H-imidazole; 2,6-dimethylpyridine; sodium tetrahydroborate; lithium borohydride; di-n-butylboryl trifluoromethanesulfonate; Dess-Martin periodane; ozone; triethylamine; triphenylphosphine; lithium diisopropyl amide; In tetrahydrofuran; methanol; dichloromethane; water; 7.1: aldol reaction;
DOI:10.1002/anie.200353313