(S)-2-((R)-2-Benzyloxycarbonylamino-2-tert-butoxycarbonyl-ethylsulfanyl)-5-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-hexanoic acid methyl ester

Base Information

Chemical Name:(S)-2-((R)-2-Benzyloxycarbonylamino-2-tert-butoxycarbonyl-ethylsulfanyl)-5-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-hexanoic acid methyl ester
CAS No.:105729-44-0
Molecular Formula:C₂₈H₄₇NO₈SSi
Molecular Weight:585.835
Hs Code.:

(S)-2-((R)-2-Benzyloxycarbonylamino-2-tert-butoxycarbonyl-ethylsulfanyl)-5-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-hexanoic acid methyl ester

Synonyms:(S)-2-((R)-2-Benzyloxycarbonylamino-2-tert-butoxycarbonyl-ethylsulfanyl)-5-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-hexanoic acid methyl ester

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Chemical Property of (S)-2-((R)-2-Benzyloxycarbonylamino-2-tert-butoxycarbonyl-ethylsulfanyl)-5-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-hexanoic acid methyl ester

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Technology Process of (S)-2-((R)-2-Benzyloxycarbonylamino-2-tert-butoxycarbonyl-ethylsulfanyl)-5-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-hexanoic acid methyl ester

There total 10 articles about (S)-2-((R)-2-Benzyloxycarbonylamino-2-tert-butoxycarbonyl-ethylsulfanyl)-5-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-hexanoic 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: 58.0%

: 105729-38-2
(S)-2-((R)-2-Benzyloxycarbonylamino-2-tert-butoxycarbonyl-ethylsulfanyl)-5-(tert-butyl-dimethyl-silanyloxy)-3-oxo-hexanoic acid methyl ester

: 105729-44-0
(S)-2-((R)-2-Benzyloxycarbonylamino-2-tert-butoxycarbonyl-ethylsulfanyl)-5-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-hexanoic acid methyl ester

Guidance literature:: With sodium tetrahydroborate; In methanol; for 0.25h;
DOI:10.1021/jo00376a052

Reference yield:

: 105729-35-9
methyl 3-oxo-5(S)-<(tert-butyldimethylsilyl)oxy>hexanoate

: 105729-44-0
(S)-2-((R)-2-Benzyloxycarbonylamino-2-tert-butoxycarbonyl-ethylsulfanyl)-5-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-hexanoic acid methyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 1.) NaH / 1.) THF, RT, 30 min, 2.) THF, RT, 15 min

2: 58 percent / sodium borohydride / methanol / 0.25 h

With sodium tetrahydroborate; sodium hydride; In methanol;
DOI:10.1021/jo00376a052

Reference yield:

: 18162-48-6
tert-butyldimethylsilyl chloride

: 105729-44-0
(S)-2-((R)-2-Benzyloxycarbonylamino-2-tert-butoxycarbonyl-ethylsulfanyl)-5-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-hexanoic acid methyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 95 percent / imidazole / dimethylformamide / 10 h / Ambient temperature

2: 72 percent / potassium hydroxide / methanol / 3.5 h / Heating

3: tetrahydrofuran / 2 h / Ambient temperature

4: 1.) dibutylmagnesium / 1.) heptane, THF, a) -78 deg C, 5 min, b) from -78 deg C to 0 deg C, 1 h, 2.) THF, RT, 16 h

5: 1.) NaH / 1.) THF, RT, 30 min, 2.) THF, RT, 15 min

6: 58 percent / sodium borohydride / methanol / 0.25 h

With 1H-imidazole; potassium hydroxide; sodium tetrahydroborate; dibutylmagnesium; sodium hydride; In tetrahydrofuran; methanol; N,N-dimethyl-formamide;
DOI:10.1021/jo00376a052