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

Base Information

Chemical Name:(3R,4S)-5-benzyloxy-4-benzyloxycarbonylamino-3-(tert-butyl-dimethyl-silanyloxy)pentanoic acid
CAS No.:752251-11-9
Molecular Formula:C₂₆H₃₇NO₆Si
Molecular Weight:487.668
Hs Code.:

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

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

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

There total 6 articles about (3R,4S)-5-benzyloxy-4-benzyloxycarbonylamino-3-(tert-butyl-dimethyl-silanyloxy)pentanoic acid 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: 54.0%

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

: 752251-11-9
(3R,4S)-5-benzyloxy-4-benzyloxycarbonylamino-3-(tert-butyl-dimethyl-silanyloxy)pentanoic acid

Guidance literature:: With sodium hydroxide; In tetrahydrofuran; methanol; at 0 - 20 ℃; for 4h;
DOI:10.1002/anie.200453909

Reference yield:

: 69739-34-0
t-butyldimethylsiyl triflate

: 752251-11-9
(3R,4S)-5-benzyloxy-4-benzyloxycarbonylamino-3-(tert-butyl-dimethyl-silanyloxy)pentanoic acid

Guidance literature:: Multi-step reaction with 2 steps

1: 78 percent / 2,6-lutidine / CH₂Cl₂ / -20 - 20 °C

2: 54 percent / aq. NaOH / tetrahydrofuran; methanol / 4 h / 0 - 20 °C

With 2,6-dimethylpyridine; sodium hydroxide; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1002/anie.200453909

Reference yield:

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

: 752251-11-9
(3R,4S)-5-benzyloxy-4-benzyloxycarbonylamino-3-(tert-butyl-dimethyl-silanyloxy)pentanoic acid

Guidance literature:: Multi-step reaction with 5 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

5.1: 54 percent / aq. NaOH / tetrahydrofuran; methanol / 4 h / 0 - 20 °C

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