(2S,2'R,4'R)-2-[4'-benzyloxycarbonylamino-2'-(tert-butyldiphenylsilanyloxy)-5'-methylhexanethioylamino]-3-hydroxypropionic acid methyl ester

Base Information

Chemical Name:(2S,2'R,4'R)-2-[4'-benzyloxycarbonylamino-2'-(tert-butyldiphenylsilanyloxy)-5'-methylhexanethioylamino]-3-hydroxypropionic acid methyl ester
CAS No.:796039-41-3
Molecular Formula:C₃₅H₄₆N₂O₆SSi
Molecular Weight:650.912
Hs Code.:

(2S,2'R,4'R)-2-[4'-benzyloxycarbonylamino-2'-(tert-butyldiphenylsilanyloxy)-5'-methylhexanethioylamino]-3-hydroxypropionic acid methyl ester

Synonyms:(2S,2'R,4'R)-2-[4'-benzyloxycarbonylamino-2'-(tert-butyldiphenylsilanyloxy)-5'-methylhexanethioylamino]-3-hydroxypropionic acid methyl ester

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Chemical Property of (2S,2'R,4'R)-2-[4'-benzyloxycarbonylamino-2'-(tert-butyldiphenylsilanyloxy)-5'-methylhexanethioylamino]-3-hydroxypropionic acid methyl ester

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Technology Process of (2S,2'R,4'R)-2-[4'-benzyloxycarbonylamino-2'-(tert-butyldiphenylsilanyloxy)-5'-methylhexanethioylamino]-3-hydroxypropionic acid methyl ester

There total 9 articles about (2S,2'R,4'R)-2-[4'-benzyloxycarbonylamino-2'-(tert-butyldiphenylsilanyloxy)-5'-methylhexanethioylamino]-3-hydroxypropionic 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: 67.0%

: 796039-39-9
(4S,1'R,3'R)-2-[3'-benzyloxycarbonylamino-1'-(tert-butyldiphenylsilanyloxy)-4'-methylpentyl]-4,5-dihydrooxazole-4-carboxylic acid methyl ester

: 796039-41-3
(2S,2'R,4'R)-2-[4'-benzyloxycarbonylamino-2'-(tert-butyldiphenylsilanyloxy)-5'-methylhexanethioylamino]-3-hydroxypropionic acid methyl ester

Guidance literature:: With hydrogen sulfide; triethylamine; In methanol; at 20 ℃; for 72h;
DOI:10.1021/ol048252i

Reference yield:

: 6216-65-5
N-benzyloxycarbonyl-L-valinol

: 796039-41-3
(2S,2'R,4'R)-2-[4'-benzyloxycarbonylamino-2'-(tert-butyldiphenylsilanyloxy)-5'-methylhexanethioylamino]-3-hydroxypropionic acid methyl ester

Guidance literature:: Multi-step reaction with 9 steps

1.1: NaBr; TEMPO; NaOCl / H₂O; toluene; ethyl acetate / 4 h / 0 °C

2.1: 3.9 g / CH₂Cl₂ / 14 h / 0 - 20 °C

3.1: 80 percent / rac-BINAP; t-BuONa; CuCl / polymethylhydrosiloxane / toluene / 72 h / 20 °C

4.1: NaHMDS / tetrahydrofuran / 0.5 h / -78 °C

4.2: 66 percent / (+/-)-trans-2-(phenylsulfonyl)-3-phenyloxaziridine / tetrahydrofuran / 1 h / -78 °C

5.1: 92 percent / imidazole / dimethylformamide / 72 h / 60 °C

6.1: LiOH*H₂O / tetrahydrofuran; H₂O / 12 h / 20 °C

7.1: 0.35 g / Et₃N; DEPBT / tetrahydrofuran / 3.5 h / 20 °C

8.1: 72 percent / DAST / tetrahydrofuran / 1 h / -78 °C

9.1: 67 percent / Et₃N; H₂S / methanol / 72 h / 20 °C

With 1H-imidazole; 2,2,6,6-tetramethyl-piperidine-N-oxyl; lithium hydroxide; sodium hypochlorite; hydrogen sulfide; sodium hexamethyldisilazane; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; triethylamine; 4,4'-diaminostilbene-2,2'-disulfonic acid; 3-[(diethoxyphosphinyl)oxy]-1,2,3-benzotriazin-4(3H)-one; sodium bromide; copper(l) chloride; sodium t-butanolate; polymethylhydrosiloxane; In tetrahydrofuran; methanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; toluene; 2.1: Wiitig olefination;
DOI:10.1021/ol048252i

Reference yield:

: 138754-84-4,95500-73-5
N-benzyloxycarbonyl-L-valinal

: 796039-41-3
(2S,2'R,4'R)-2-[4'-benzyloxycarbonylamino-2'-(tert-butyldiphenylsilanyloxy)-5'-methylhexanethioylamino]-3-hydroxypropionic acid methyl ester

Guidance literature:: Multi-step reaction with 8 steps

1.1: 3.9 g / CH₂Cl₂ / 14 h / 0 - 20 °C

2.1: 80 percent / rac-BINAP; t-BuONa; CuCl / polymethylhydrosiloxane / toluene / 72 h / 20 °C

3.1: NaHMDS / tetrahydrofuran / 0.5 h / -78 °C

3.2: 66 percent / (+/-)-trans-2-(phenylsulfonyl)-3-phenyloxaziridine / tetrahydrofuran / 1 h / -78 °C

4.1: 92 percent / imidazole / dimethylformamide / 72 h / 60 °C

5.1: LiOH*H₂O / tetrahydrofuran; H₂O / 12 h / 20 °C

6.1: 0.35 g / Et₃N; DEPBT / tetrahydrofuran / 3.5 h / 20 °C

7.1: 72 percent / DAST / tetrahydrofuran / 1 h / -78 °C

8.1: 67 percent / Et₃N; H₂S / methanol / 72 h / 20 °C

With 1H-imidazole; lithium hydroxide; hydrogen sulfide; sodium hexamethyldisilazane; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; triethylamine; 4,4'-diaminostilbene-2,2'-disulfonic acid; 3-[(diethoxyphosphinyl)oxy]-1,2,3-benzotriazin-4(3H)-one; copper(l) chloride; sodium t-butanolate; polymethylhydrosiloxane; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; 1.1: Wiitig olefination;
DOI:10.1021/ol048252i