(2R,3S)-1-Benzyl-2-[(R)-3-benzyloxy-1-(tert-butyl-dimethyl-silanyloxymethyl)-propyl]-3-(tert-butyl-dimethyl-silanyloxy)-pyrrolidine

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Chemical Name:(2R,3S)-1-Benzyl-2-[(R)-3-benzyloxy-1-(tert-butyl-dimethyl-silanyloxymethyl)-propyl]-3-(tert-butyl-dimethyl-silanyloxy)-pyrrolidine
CAS No.:176376-14-0
Molecular Formula:C₃₄H₅₇NO₃Si₂
Molecular Weight:584.002
Hs Code.:

Synonyms:(2R,3S)-1-Benzyl-2-[(R)-3-benzyloxy-1-(tert-butyl-dimethyl-silanyloxymethyl)-propyl]-3-(tert-butyl-dimethyl-silanyloxy)-pyrrolidine

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Chemical Property of (2R,3S)-1-Benzyl-2-[(R)-3-benzyloxy-1-(tert-butyl-dimethyl-silanyloxymethyl)-propyl]-3-(tert-butyl-dimethyl-silanyloxy)-pyrrolidine

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Technology Process of (2R,3S)-1-Benzyl-2-[(R)-3-benzyloxy-1-(tert-butyl-dimethyl-silanyloxymethyl)-propyl]-3-(tert-butyl-dimethyl-silanyloxy)-pyrrolidine

There total 6 articles about (2R,3S)-1-Benzyl-2-[(R)-3-benzyloxy-1-(tert-butyl-dimethyl-silanyloxymethyl)-propyl]-3-(tert-butyl-dimethyl-silanyloxy)-pyrrolidine 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%

: 176376-13-9
(4S,5R)-1-Benzyl-5-[(R)-3-benzyloxy-1-(tert-butyl-dimethyl-silanyloxymethyl)-propyl]-4-(tert-butyl-dimethyl-silanyloxy)-pyrrolidin-2-one

: 176376-14-0
(2R,3S)-1-Benzyl-2-[(R)-3-benzyloxy-1-(tert-butyl-dimethyl-silanyloxymethyl)-propyl]-3-(tert-butyl-dimethyl-silanyloxy)-pyrrolidine

Guidance literature:: With dimethylsulfide borane complex; In tetrahydrofuran; for 16h; Ambient temperature;
DOI:10.1021/jo9513020

Reference yield:

: 69739-34-0
t-butyldimethylsiyl triflate

: 176376-14-0
(2R,3S)-1-Benzyl-2-[(R)-3-benzyloxy-1-(tert-butyl-dimethyl-silanyloxymethyl)-propyl]-3-(tert-butyl-dimethyl-silanyloxy)-pyrrolidine

Guidance literature:: Multi-step reaction with 2 steps

1: 64 percent / 2,6-lutidine / CH₂Cl₂ / 3 h / 0 °C

2: 73 percent / BH₃Me₂S / tetrahydrofuran / 16 h / Ambient temperature

With 2,6-dimethylpyridine; dimethylsulfide borane complex; In tetrahydrofuran; dichloromethane;
DOI:10.1021/jo9513020

Reference yield:

: (S)-3-(4-Benzyloxy-butyryl)-4-isopropyl-oxazolidin-2-one

: 176376-14-0
(2R,3S)-1-Benzyl-2-[(R)-3-benzyloxy-1-(tert-butyl-dimethyl-silanyloxymethyl)-propyl]-3-(tert-butyl-dimethyl-silanyloxy)-pyrrolidine

Guidance literature:: Multi-step reaction with 4 steps

1: 1.) nBuBOTf, diisopropylethalamine / 1) CH₂Cl₂, 0 deg C, 45 min; 2) CH₂Cl₂, 0 deg C, 15 min, rt, 4 h

2: 67 percent / LiBH₄ / tetrahydrofuran / 1) 0 deg C, 5 min; 2) rt, 4 h

3: 64 percent / 2,6-lutidine / CH₂Cl₂ / 3 h / 0 °C

4: 73 percent / BH₃Me₂S / tetrahydrofuran / 16 h / Ambient temperature

With 2,6-dimethylpyridine; lithium borohydride; dimethylsulfide borane complex; nBuBOTf; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane;
DOI:10.1021/jo9513020