(3R,5S,6S)-6-benzyloxycarbonylamino-3,5,7-tris-(tert-butyl-dimethyl-silanyloxy)-heptanoic acid methyl ester

Base Information

Chemical Name:(3R,5S,6S)-6-benzyloxycarbonylamino-3,5,7-tris-(tert-butyl-dimethyl-silanyloxy)-heptanoic acid methyl ester
CAS No.:823235-77-4
Molecular Formula:C₃₄H₆₅NO₇Si₃
Molecular Weight:684.149
Hs Code.:

Synonyms:(3R,5S,6S)-6-benzyloxycarbonylamino-3,5,7-tris-(tert-butyl-dimethyl-silanyloxy)-heptanoic acid methyl ester

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Chemical Property of (3R,5S,6S)-6-benzyloxycarbonylamino-3,5,7-tris-(tert-butyl-dimethyl-silanyloxy)-heptanoic acid methyl ester

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Technology Process of (3R,5S,6S)-6-benzyloxycarbonylamino-3,5,7-tris-(tert-butyl-dimethyl-silanyloxy)-heptanoic acid methyl ester

There total 3 articles about (3R,5S,6S)-6-benzyloxycarbonylamino-3,5,7-tris-(tert-butyl-dimethyl-silanyloxy)-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: 75.0%

: 823235-89-8
(3R,5S,6S)-6-benzyloxycarbonylamino-7-(tert-butyl-dimethyl-silanyloxy)-3,5-dihydroxy-heptanoic acid methyl ester

: 69739-34-0
t-butyldimethylsiyl triflate

: 823235-77-4
(3R,5S,6S)-6-benzyloxycarbonylamino-3,5,7-tris-(tert-butyl-dimethyl-silanyloxy)-heptanoic acid methyl ester

Guidance literature:: With 2,6-dimethylpyridine; In dichloromethane; at -20 ℃; for 1.25h;
DOI:10.1021/ol048068x DOI:10.1021/jo701402b

Reference yield:

: 823235-74-1
(5S,6S)-6-benzyloxycarbonylamino-7-(tert-butyl-dimethyl-silanyloxy)-5-hydroxy-3-oxo-heptanoic acid methyl ester

: 823235-77-4
(3R,5S,6S)-6-benzyloxycarbonylamino-3,5,7-tris-(tert-butyl-dimethyl-silanyloxy)-heptanoic acid methyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: Me₄N(OAc)3BH; AcOH / acetonitrile / -35 - 0 °C

2: 75 percent / 2,6-lutidine / CH₂Cl₂ / 1.25 h / -20 °C

With 2,6-dimethylpyridine; acetic acid; tetramethylammonium triacetoxyborohydride; In dichloromethane; acetonitrile;
DOI:10.1021/ol048068x

Reference yield:

: 359455-05-3
[(1S,2S)-1-(tert-butyl-dimethyl-silanyloxymethyl)-3-(2,2-dimethyl-6-oxo-6H-[1,3]dioxin-4-yl)-2-hydroxy-propyl]-carbamic acid benzyl ester

: 823235-77-4
(3R,5S,6S)-6-benzyloxycarbonylamino-3,5,7-tris-(tert-butyl-dimethyl-silanyloxy)-heptanoic acid methyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 85 percent / toluene / 4 h / Heating

2: Me₄N(OAc)3BH; AcOH / acetonitrile / -35 - 0 °C

3: 75 percent / 2,6-lutidine / CH₂Cl₂ / 1.25 h / -20 °C

With 2,6-dimethylpyridine; acetic acid; tetramethylammonium triacetoxyborohydride; In dichloromethane; toluene; acetonitrile;
DOI:10.1021/ol048068x