(2S,3S,5S)-2-Benzyl-3-(tert-butyl-dimethyl-silanyloxy)-5-((R)-1,2-dihydroxy-ethyl)-pyrrolidine-1-carboxylic acid benzyl ester

Base Information

Chemical Name:(2S,3S,5S)-2-Benzyl-3-(tert-butyl-dimethyl-silanyloxy)-5-((R)-1,2-dihydroxy-ethyl)-pyrrolidine-1-carboxylic acid benzyl ester
CAS No.:199392-57-9
Molecular Formula:C₂₇H₃₉NO₅Si
Molecular Weight:485.696
Hs Code.:

Synonyms:(2S,3S,5S)-2-Benzyl-3-(tert-butyl-dimethyl-silanyloxy)-5-((R)-1,2-dihydroxy-ethyl)-pyrrolidine-1-carboxylic acid benzyl ester

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Chemical Property of (2S,3S,5S)-2-Benzyl-3-(tert-butyl-dimethyl-silanyloxy)-5-((R)-1,2-dihydroxy-ethyl)-pyrrolidine-1-carboxylic acid benzyl ester

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Technology Process of (2S,3S,5S)-2-Benzyl-3-(tert-butyl-dimethyl-silanyloxy)-5-((R)-1,2-dihydroxy-ethyl)-pyrrolidine-1-carboxylic acid benzyl ester

There total 7 articles about (2S,3S,5S)-2-Benzyl-3-(tert-butyl-dimethyl-silanyloxy)-5-((R)-1,2-dihydroxy-ethyl)-pyrrolidine-1-carboxylic acid benzyl 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: 33.0%

: 199392-55-7
[(E)-(1S,2S)-1-Benzyl-2-(tert-butyl-dimethyl-silanyloxy)-6-hydroxy-hex-4-enyl]-carbamic acid benzyl ester

: 199392-57-9
(2S,3S,5S)-2-Benzyl-3-(tert-butyl-dimethyl-silanyloxy)-5-((R)-1,2-dihydroxy-ethyl)-pyrrolidine-1-carboxylic acid benzyl ester

: 199392-56-8
[(1S,2S)-1-Benzyl-2-(tert-butyl-dimethyl-silanyloxy)-3-((2R,3R)-3-hydroxymethyl-oxiranyl)-propyl]-carbamic acid benzyl ester

Guidance literature:: With titanium(IV) isopropylate; tert.-butylhydroperoxide; diethyl (2S,3S)-tartrate; In dichloromethane; toluene; at -23 ℃; for 36h;
DOI:10.1055/s-1997-1347

Reference yield:

: 199392-53-5
[(1S,2S)-1-Benzyl-2-(tert-butyl-dimethyl-silanyloxy)-4-phenylsulfanyl-hex-5-enyl]-carbamic acid benzyl ester

: 199392-57-9
(2S,3S,5S)-2-Benzyl-3-(tert-butyl-dimethyl-silanyloxy)-5-((R)-1,2-dihydroxy-ethyl)-pyrrolidine-1-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: NaIO₄ / methanol; H₂O / 36 h

2: 88 percent / P(OMe)3 / methanol / 48 h

3: 45 percent / Ti(Oi-Pr)4, t-BuOOH, D-(-)-DET / CH₂Cl₂; toluene / 36 h / -23 °C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; sodium periodate; diethyl (2S,3S)-tartrate; phosphorous acid trimethyl ester; In methanol; dichloromethane; water; toluene;
DOI:10.1055/s-1997-1347

Reference yield:

: 199392-52-4
((1S,2S)-1-Benzyl-2-hydroxy-4-phenylsulfanyl-hex-5-enyl)-carbamic acid benzyl ester

: 199392-57-9
(2S,3S,5S)-2-Benzyl-3-(tert-butyl-dimethyl-silanyloxy)-5-((R)-1,2-dihydroxy-ethyl)-pyrrolidine-1-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 97 percent / imidazole / dimethylformamide / Ambient temperature

2: NaIO₄ / methanol; H₂O / 36 h

3: 88 percent / P(OMe)3 / methanol / 48 h

4: 45 percent / Ti(Oi-Pr)4, t-BuOOH, D-(-)-DET / CH₂Cl₂; toluene / 36 h / -23 °C

With 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; sodium periodate; diethyl (2S,3S)-tartrate; phosphorous acid trimethyl ester; In methanol; dichloromethane; water; N,N-dimethyl-formamide; toluene;
DOI:10.1055/s-1997-1347