methyl (3S,5S,6S)-6-(((benzyloxy)carbonyl)amino)-7-((tert-butyldimethylsilyl)oxy)-3,5-dihydroxyheptanoate

Base Information

Chemical Name:methyl (3S,5S,6S)-6-(((benzyloxy)carbonyl)amino)-7-((tert-butyldimethylsilyl)oxy)-3,5-dihydroxyheptanoate
CAS No.:823235-88-7
Molecular Formula:C₂₂H₃₇NO₇Si
Molecular Weight:455.624
Hs Code.:

Synonyms:methyl (3S,5S,6S)-6-(((benzyloxy)carbonyl)amino)-7-((tert-butyldimethylsilyl)oxy)-3,5-dihydroxyheptanoate

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Chemical Property of methyl (3S,5S,6S)-6-(((benzyloxy)carbonyl)amino)-7-((tert-butyldimethylsilyl)oxy)-3,5-dihydroxyheptanoate

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Technology Process of methyl (3S,5S,6S)-6-(((benzyloxy)carbonyl)amino)-7-((tert-butyldimethylsilyl)oxy)-3,5-dihydroxyheptanoate

There total 6 articles about methyl (3S,5S,6S)-6-(((benzyloxy)carbonyl)amino)-7-((tert-butyldimethylsilyl)oxy)-3,5-dihydroxyheptanoate 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:

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

: 823235-88-7
methyl (3S,5S,6S)-6-(((benzyloxy)carbonyl)amino)-7-((tert-butyldimethylsilyl)oxy)-3,5-dihydroxyheptanoate

Guidance literature:: With acetic acid; tetramethylammonium triacetoxyborohydride; In acetonitrile; at -35 ℃; diastereoselective reaction;
DOI:10.1021/jacs.1c09616

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

: 823235-88-7
methyl (3S,5S,6S)-6-(((benzyloxy)carbonyl)amino)-7-((tert-butyldimethylsilyl)oxy)-3,5-dihydroxyheptanoate

Guidance literature:: Multi-step reaction with 2 steps

1: 85 percent / toluene / 4 h / Heating

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

With acetic acid; tetramethylammonium triacetoxyborohydride; In toluene; acetonitrile;
DOI:10.1021/ol048068x

Reference yield:

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

: 823235-88-7
methyl (3S,5S,6S)-6-(((benzyloxy)carbonyl)amino)-7-((tert-butyldimethylsilyl)oxy)-3,5-dihydroxyheptanoate

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

Guidance literature:: With acetic acid; tetramethylammonium triacetoxyborohydride; In acetonitrile; at -35 - 0 ℃; Title compound not separated from byproducts;
DOI:10.1021/ol048068x