(3'S,2'S,2S,3R,6R)-6-[3'-benzyloxycarbonylamino butyric acid methyl ester-2'-yloxy]-2-tert-butyldimethylsilanyloxy-6H-pyran-3-ol

Base Information

Chemical Name:(3'S,2'S,2S,3R,6R)-6-[3'-benzyloxycarbonylamino butyric acid methyl ester-2'-yloxy]-2-tert-butyldimethylsilanyloxy-6H-pyran-3-ol
CAS No.:623157-55-1
Molecular Formula:C₂₅H₃₉NO₈Si
Molecular Weight:509.672
Hs Code.:

Synonyms:(3'S,2'S,2S,3R,6R)-6-[3'-benzyloxycarbonylamino butyric acid methyl ester-2'-yloxy]-2-tert-butyldimethylsilanyloxy-6H-pyran-3-ol

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Chemical Property of (3'S,2'S,2S,3R,6R)-6-[3'-benzyloxycarbonylamino butyric acid methyl ester-2'-yloxy]-2-tert-butyldimethylsilanyloxy-6H-pyran-3-ol

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Technology Process of (3'S,2'S,2S,3R,6R)-6-[3'-benzyloxycarbonylamino butyric acid methyl ester-2'-yloxy]-2-tert-butyldimethylsilanyloxy-6H-pyran-3-ol

There total 4 articles about (3'S,2'S,2S,3R,6R)-6-[3'-benzyloxycarbonylamino butyric acid methyl ester-2'-yloxy]-2-tert-butyldimethylsilanyloxy-6H-pyran-3-ol 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: 91.0%

: 623157-54-0
(3'S,2'S,2S,6R)-6-[3'-benzyloxycarbonylamino butyric acid methyl ester-2'-yloxy]-2-tert-butyldimethylsilanyloxy-6H-pyran-3-one

: 623157-55-1
(3'S,2'S,2S,3R,6R)-6-[3'-benzyloxycarbonylamino butyric acid methyl ester-2'-yloxy]-2-tert-butyldimethylsilanyloxy-6H-pyran-3-ol

Guidance literature:: With sodium tetrahydroborate; In methanol; dichloromethane; at -78 ℃; for 3h;
DOI:10.1021/ja037097k

Reference yield:

: 222986-37-0
(S)-2-((tert-butyldimethylsilyl)oxy)-1-(furan-2-yl)ethan-1-ol

: 623157-55-1
(3'S,2'S,2S,3R,6R)-6-[3'-benzyloxycarbonylamino butyric acid methyl ester-2'-yloxy]-2-tert-butyldimethylsilanyloxy-6H-pyran-3-ol

Guidance literature:: Multi-step reaction with 4 steps

1: 95 percent / aq. NaHCO₃; NaOAc; NBS / tetrahydrofuran / 1 h / 0 °C

2: DMAP / CH₂Cl₂ / 1 h / 0 °C

3: 90 percent / PPh₃; Pd₂(DBA)3*CHCl₃ / CH₂Cl₂ / 3 h / 0 °C

4: 91 percent / NaBH₄ / CH₂Cl₂; methanol / 3 h / -78 °C

With dmap; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; sodium tetrahydroborate; N-Bromosuccinimide; sodium acetate; sodium hydrogencarbonate; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1021/ja037097k

Reference yield:

: 302348-82-9
(2S)-2-(((tert-butyldimethylsilyl)oxy)methyl)-6-hydroxy-2H-pyran-3(6H)-one

: 623157-55-1
(3'S,2'S,2S,3R,6R)-6-[3'-benzyloxycarbonylamino butyric acid methyl ester-2'-yloxy]-2-tert-butyldimethylsilanyloxy-6H-pyran-3-ol

Guidance literature:: Multi-step reaction with 3 steps

1: DMAP / CH₂Cl₂ / 1 h / 0 °C

2: 90 percent / PPh₃; Pd₂(DBA)3*CHCl₃ / CH₂Cl₂ / 3 h / 0 °C

3: 91 percent / NaBH₄ / CH₂Cl₂; methanol / 3 h / -78 °C

With dmap; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; sodium tetrahydroborate; triphenylphosphine; In methanol; dichloromethane;
DOI:10.1021/ja037097k