(3R,4S)-5-benzyloxy-4-benzyloxycarbonylamino-3-(tert-butyl-dimethyl-silanyloxy)pentanoic acid methyl ester

Base Information

Chemical Name:(3R,4S)-5-benzyloxy-4-benzyloxycarbonylamino-3-(tert-butyl-dimethyl-silanyloxy)pentanoic acid methyl ester
CAS No.:752251-10-8
Molecular Formula:C₂₇H₃₉NO₆Si
Molecular Weight:501.695
Hs Code.:

Synonyms:(3R,4S)-5-benzyloxy-4-benzyloxycarbonylamino-3-(tert-butyl-dimethyl-silanyloxy)pentanoic acid methyl ester

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Chemical Property of (3R,4S)-5-benzyloxy-4-benzyloxycarbonylamino-3-(tert-butyl-dimethyl-silanyloxy)pentanoic acid methyl ester

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Technology Process of (3R,4S)-5-benzyloxy-4-benzyloxycarbonylamino-3-(tert-butyl-dimethyl-silanyloxy)pentanoic acid methyl ester

There total 4 articles about (3R,4S)-5-benzyloxy-4-benzyloxycarbonylamino-3-(tert-butyl-dimethyl-silanyloxy)pentanoic 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: 78.0%

: 69739-34-0
t-butyldimethylsiyl triflate

: 752251-09-5
(3R,4S)-5-benzyloxy-4-benzyloxycarbonylamino-3-hydroxy-pentanoic acid methyl ester

: 752251-10-8
(3R,4S)-5-benzyloxy-4-benzyloxycarbonylamino-3-(tert-butyl-dimethyl-silanyloxy)pentanoic acid methyl ester

Guidance literature:: With 2,6-dimethylpyridine; In dichloromethane; at -20 - 20 ℃;
DOI:10.1002/anie.200453909

Reference yield:

: 20806-43-3
Z-Ser(Bzl)-OH

: 752251-10-8
(3R,4S)-5-benzyloxy-4-benzyloxycarbonylamino-3-(tert-butyl-dimethyl-silanyloxy)pentanoic acid methyl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: tetrahydrofuran / 2 h / 0 - 20 °C

2.1: MgCl₂ / tetrahydrofuran / 5 h / Heating

2.2: 34.2 g / tetrahydrofuran / 16 h / 20 °C

3.1: 48 percent / NaBH₄ / methanol; diethyl ether / 6 h / -60 °C

4.1: 78 percent / 2,6-lutidine / CH₂Cl₂ / -20 - 20 °C

With 2,6-dimethylpyridine; sodium tetrahydroborate; magnesium chloride; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; 2.2: Claisen condensation;
DOI:10.1002/anie.200453909

Reference yield:

: 752251-08-4
(4S)-5-benzyloxy-4-benzyloxycarbonylamino-3-oxo-pentanoic acid methyl ester

: 752251-10-8
(3R,4S)-5-benzyloxy-4-benzyloxycarbonylamino-3-(tert-butyl-dimethyl-silanyloxy)pentanoic acid methyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 48 percent / NaBH₄ / methanol; diethyl ether / 6 h / -60 °C

2: 78 percent / 2,6-lutidine / CH₂Cl₂ / -20 - 20 °C

With 2,6-dimethylpyridine; sodium tetrahydroborate; In methanol; diethyl ether; dichloromethane;
DOI:10.1002/anie.200453909