(2'S,2S,3R,6R)-6-[2'-benzyloxycarbonylamino propionoic acid methyl ester-1'-yloxy]-2-tert-butyldimethylsilanyloxy-6H-pyran-3-one

Base Information

Chemical Name:(2'S,2S,3R,6R)-6-[2'-benzyloxycarbonylamino propionoic acid methyl ester-1'-yloxy]-2-tert-butyldimethylsilanyloxy-6H-pyran-3-one
CAS No.:623157-52-8
Molecular Formula:C₂₄H₃₇NO₈Si
Molecular Weight:495.645
Hs Code.:

Synonyms:(2'S,2S,3R,6R)-6-[2'-benzyloxycarbonylamino propionoic acid methyl ester-1'-yloxy]-2-tert-butyldimethylsilanyloxy-6H-pyran-3-one

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Chemical Property of (2'S,2S,3R,6R)-6-[2'-benzyloxycarbonylamino propionoic acid methyl ester-1'-yloxy]-2-tert-butyldimethylsilanyloxy-6H-pyran-3-one

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Technology Process of (2'S,2S,3R,6R)-6-[2'-benzyloxycarbonylamino propionoic acid methyl ester-1'-yloxy]-2-tert-butyldimethylsilanyloxy-6H-pyran-3-one

There total 4 articles about (2'S,2S,3R,6R)-6-[2'-benzyloxycarbonylamino propionoic acid methyl ester-1'-yloxy]-2-tert-butyldimethylsilanyloxy-6H-pyran-3-one 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: 87.0%

: 623157-51-7
(2'S,2S,6R)-6-[2'-benzyloxycarbonylamino propionoic acid methyl ester-1'-yloxy]-2-tert-butyldimethylsilanyloxy-6H-pyran-3-one

: 623157-52-8
(2'S,2S,3R,6R)-6-[2'-benzyloxycarbonylamino propionoic acid methyl ester-1'-yloxy]-2-tert-butyldimethylsilanyloxy-6H-pyran-3-one

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

: 623157-52-8
(2'S,2S,3R,6R)-6-[2'-benzyloxycarbonylamino propionoic acid methyl ester-1'-yloxy]-2-tert-butyldimethylsilanyloxy-6H-pyran-3-one

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

4: 87 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

: 623157-52-8
(2'S,2S,3R,6R)-6-[2'-benzyloxycarbonylamino propionoic acid methyl ester-1'-yloxy]-2-tert-butyldimethylsilanyloxy-6H-pyran-3-one

Guidance literature:: Multi-step reaction with 3 steps

1: DMAP / CH₂Cl₂ / 1 h / 0 °C

2: 87 percent / PPh₃; Pd₂(DBA)3*CHCl₃ / CH₂Cl₂ / 3 h / 0 °C

3: 87 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