(Z)-(S)-2-((R)-2-Benzyloxycarbonylamino-2-tert-butoxycarbonyl-ethylsulfanyl)-5-(tert-butyl-dimethyl-silanyloxy)-hex-2-enoic acid methyl ester

Base Information

Chemical Name:(Z)-(S)-2-((R)-2-Benzyloxycarbonylamino-2-tert-butoxycarbonyl-ethylsulfanyl)-5-(tert-butyl-dimethyl-silanyloxy)-hex-2-enoic acid methyl ester
CAS No.:105729-45-1
Molecular Formula:C₂₈H₄₅NO₇SSi
Molecular Weight:567.819
Hs Code.:

Synonyms:(Z)-(S)-2-((R)-2-Benzyloxycarbonylamino-2-tert-butoxycarbonyl-ethylsulfanyl)-5-(tert-butyl-dimethyl-silanyloxy)-hex-2-enoic acid methyl ester

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Chemical Property of (Z)-(S)-2-((R)-2-Benzyloxycarbonylamino-2-tert-butoxycarbonyl-ethylsulfanyl)-5-(tert-butyl-dimethyl-silanyloxy)-hex-2-enoic acid methyl ester

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Technology Process of (Z)-(S)-2-((R)-2-Benzyloxycarbonylamino-2-tert-butoxycarbonyl-ethylsulfanyl)-5-(tert-butyl-dimethyl-silanyloxy)-hex-2-enoic acid methyl ester

There total 11 articles about (Z)-(S)-2-((R)-2-Benzyloxycarbonylamino-2-tert-butoxycarbonyl-ethylsulfanyl)-5-(tert-butyl-dimethyl-silanyloxy)-hex-2-enoic 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: 73.0%

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

: 105729-45-1
(Z)-(S)-2-((R)-2-Benzyloxycarbonylamino-2-tert-butoxycarbonyl-ethylsulfanyl)-5-(tert-butyl-dimethyl-silanyloxy)-hex-2-enoic acid methyl ester

Guidance literature:: With methanesulfonyl chloride; triethylamine; In dichloromethane; for 0.416667h; Ambient temperature;
DOI:10.1021/jo00376a052

Reference yield:

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

: 105729-45-1
(Z)-(S)-2-((R)-2-Benzyloxycarbonylamino-2-tert-butoxycarbonyl-ethylsulfanyl)-5-(tert-butyl-dimethyl-silanyloxy)-hex-2-enoic acid methyl ester

Guidance literature:: Multi-step reaction with 3 steps

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

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

3: 73 percent / triethylamine, methanesulfonyl chloride / CH₂Cl₂ / 0.42 h / Ambient temperature

With sodium tetrahydroborate; sodium hydride; methanesulfonyl chloride; triethylamine; In methanol; dichloromethane;
DOI:10.1021/jo00376a052

Reference yield:

: 18162-48-6
tert-butyldimethylsilyl chloride

: 105729-45-1
(Z)-(S)-2-((R)-2-Benzyloxycarbonylamino-2-tert-butoxycarbonyl-ethylsulfanyl)-5-(tert-butyl-dimethyl-silanyloxy)-hex-2-enoic acid methyl ester

Guidance literature:: Multi-step reaction with 7 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

7: 73 percent / triethylamine, methanesulfonyl chloride / CH₂Cl₂ / 0.42 h / Ambient temperature

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