7-benzyloxy-(6S)-6-benzyloxycarbonylamino-(3S,5R)-3,5-bis(tert-butyldimethylsilanyloxy)heptanoic acid methyl ester

Base Information

Chemical Name:7-benzyloxy-(6S)-6-benzyloxycarbonylamino-(3S,5R)-3,5-bis(tert-butyldimethylsilanyloxy)heptanoic acid methyl ester
CAS No.:823235-75-2
Molecular Formula:C₃₅H₅₇NO₇Si₂
Molecular Weight:660.011
Hs Code.:

Synonyms:7-benzyloxy-(6S)-6-benzyloxycarbonylamino-(3S,5R)-3,5-bis(tert-butyldimethylsilanyloxy)heptanoic acid methyl ester

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Chemical Property of 7-benzyloxy-(6S)-6-benzyloxycarbonylamino-(3S,5R)-3,5-bis(tert-butyldimethylsilanyloxy)heptanoic acid methyl ester

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Technology Process of 7-benzyloxy-(6S)-6-benzyloxycarbonylamino-(3S,5R)-3,5-bis(tert-butyldimethylsilanyloxy)heptanoic acid methyl ester

There total 2 articles about 7-benzyloxy-(6S)-6-benzyloxycarbonylamino-(3S,5R)-3,5-bis(tert-butyldimethylsilanyloxy)heptanoic acid methyl ester 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:

: (3S,5R,6S)-7-Benzyloxy-6-benzyloxycarbonylamino-3,5-dihydroxy-heptanoic acid methyl ester

: 69739-34-0
t-butyldimethylsiyl triflate

: 823235-75-2
7-benzyloxy-(6S)-6-benzyloxycarbonylamino-(3S,5R)-3,5-bis(tert-butyldimethylsilanyloxy)heptanoic acid methyl ester

Guidance literature:: With 2,6-dimethylpyridine; In dichloromethane; at -20 ℃; for 3h;
DOI:10.1021/ol048068x DOI:10.1021/jo701402b

Reference yield:

: 752251-13-1
7-benzyloxy-(6S)-6-benzyloxycarbonylamino-(5R)-5-hydroxy-3-oxoheptanoic acid methyl ester

: 823235-75-2
7-benzyloxy-(6S)-6-benzyloxycarbonylamino-(3S,5R)-3,5-bis(tert-butyldimethylsilanyloxy)heptanoic acid methyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: Et₃B; pivalic acid; NaBH₄ / tetrahydrofuran; methanol; hexane / 4 h / -70 °C

2: 395 mg / 2,6-lutidine / CH₂Cl₂ / 3 h / -20 °C

With 2,6-dimethylpyridine; sodium tetrahydroborate; triethyl borane; Trimethylacetic acid; In tetrahydrofuran; methanol; hexane; dichloromethane;
DOI:10.1021/ol048068x

Reference yield:

: 823235-75-2
7-benzyloxy-(6S)-6-benzyloxycarbonylamino-(3S,5R)-3,5-bis(tert-butyldimethylsilanyloxy)heptanoic acid methyl ester

: (3S,5R,6S)-6-(2-Benzyloxy-benzoylamino)-3,5-bis-(tert-butyl-dimethyl-silanyloxy)-7-hydroxy-heptanoic acid methyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: H₂ / Pd/C / methanol / 4 h / 20 °C

2: EDC*HCl; HOBt; NMM / CH₂Cl₂ / 20 h / 20 °C

With 4-methyl-morpholine; hydrogen; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; palladium on activated charcoal; In methanol; dichloromethane;
DOI:10.1021/ol048068x