(2R,4R)-4-benzyloxycarbonylamino-2-(tert-butyldiphenylsilanyloxy)-5-methylhexanoic acid methyl ester

Base Information

Chemical Name:(2R,4R)-4-benzyloxycarbonylamino-2-(tert-butyldiphenylsilanyloxy)-5-methylhexanoic acid methyl ester
CAS No.:796039-37-7
Molecular Formula:C₃₂H₄₁NO₅Si
Molecular Weight:547.767
Hs Code.:

Synonyms:(2R,4R)-4-benzyloxycarbonylamino-2-(tert-butyldiphenylsilanyloxy)-5-methylhexanoic acid methyl ester

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Chemical Property of (2R,4R)-4-benzyloxycarbonylamino-2-(tert-butyldiphenylsilanyloxy)-5-methylhexanoic acid methyl ester

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Technology Process of (2R,4R)-4-benzyloxycarbonylamino-2-(tert-butyldiphenylsilanyloxy)-5-methylhexanoic acid methyl ester

There total 5 articles about (2R,4R)-4-benzyloxycarbonylamino-2-(tert-butyldiphenylsilanyloxy)-5-methylhexanoic 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: 92.0%

: 58479-61-1
tert-butylchlorodiphenylsilane

: 215608-40-5
methyl (2R,4R)-4-<(benzyloxycarbonyl)amino>-2-hydroxy-5-methylhexanoate

: 796039-37-7
(2R,4R)-4-benzyloxycarbonylamino-2-(tert-butyldiphenylsilanyloxy)-5-methylhexanoic acid methyl ester

Guidance literature:: With 1H-imidazole; In N,N-dimethyl-formamide; at 60 ℃; for 72h;
DOI:10.1021/ol048252i

Reference yield:

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

: 796039-37-7
(2R,4R)-4-benzyloxycarbonylamino-2-(tert-butyldiphenylsilanyloxy)-5-methylhexanoic acid methyl ester

Guidance literature:: Multi-step reaction with 5 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

With 1H-imidazole; 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; sodium hexamethyldisilazane; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium bromide; copper(l) chloride; sodium t-butanolate; polymethylhydrosiloxane; In tetrahydrofuran; 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

: 796039-37-7
(2R,4R)-4-benzyloxycarbonylamino-2-(tert-butyldiphenylsilanyloxy)-5-methylhexanoic acid methyl ester

Guidance literature:: Multi-step reaction with 4 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

With 1H-imidazole; sodium hexamethyldisilazane; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; copper(l) chloride; sodium t-butanolate; polymethylhydrosiloxane; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene; 1.1: Wiitig olefination;
DOI:10.1021/ol048252i