(2S,5S)-1-tert-butoxycarbonyl-2-tert-butyldimethylsilyloxymethyl-3-phenylsulfonyl-5-benzyloxymethyl pyrrolidine

Base Information

• Chemical Name: (2S,5S)-1-tert-butoxycarbonyl-2-tert-butyldimethylsilyloxymethyl-3-phenylsulfonyl-5-benzyloxymethyl pyrrolidine
• CAS No.: 366786-61-0
• Molecular Formula: C₃₀H₄₅NO₆SSi
• Molecular Weight: 575.842
• Mol file: 366786-61-0.mol

Synonyms:

Chemical Property of (2S,5S)-1-tert-butoxycarbonyl-2-tert-butyldimethylsilyloxymethyl-3-phenylsulfonyl-5-benzyloxymethyl pyrrolidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,5S)-1-tert-butoxycarbonyl-2-tert-butyldimethylsilyloxymethyl-3-phenylsulfonyl-5-benzyloxymethyl pyrrolidine

There total 1 articles about (2S,5S)-1-tert-butoxycarbonyl-2-tert-butyldimethylsilyloxymethyl-3-phenylsulfonyl-5-benzyloxymethyl 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:

(2S)-1-O-benzylglycerol-2,3-bis(trifluoromethanesulfonate) (253776-34-0) + [1-benzenesulfonylmethyl-2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-carbamic acid tert-butyl ester → (2S,5S)-1-tert-butoxycarbonyl-2-tert-butyldimethylsilyloxymethyl-3-phenylsulfonyl-5-benzyloxymethyl pyrrolidine (366786-61-0)

Guidance literature:

[1-benzenesulfonylmethyl-2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-carbamic acid tert-butyl ester; With n-butyllithium; In tetrahydrofuran; at -78 ℃; for 0.5h;

(2S)-1-O-benzylglycerol-2,3-bis(trifluoromethanesulfonate); In tetrahydrofuran; at -78 - 20 ℃;

DOI:10.1016/S0040-4020(01)00537-3

Reference yield:

(2S,5S)-1-tert-butoxycarbonyl-2-tert-butyldimethylsilyloxymethyl-3-phenylsulfonyl-5-benzyloxymethyl pyrrolidine (366786-61-0) → (2S,5S)-1-tert-butoxycarbonyl-2-hydroxymethyl-3-phenylsulfonyl-5-benzyloxy-methyl pyrrolidine (366786-62-1)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 1h;

DOI:10.1016/S0040-4020(01)00537-3

Reference yield:

(2S,5S)-1-tert-butoxycarbonyl-2-tert-butyldimethylsilyloxymethyl-3-phenylsulfonyl-5-benzyloxymethyl pyrrolidine (366786-61-0) → (2S,5R)-1-tert-butoxycarbonyl-5-hydroxymethyl-2-benzyloxymethyl pyrrolidine (152612-42-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 2.31 g / tetrabutylammonium fluoride / tetrahydrofuran / 1 h / 20 °C

2: 92 percent / Na₂HPO₄; Na-Hg / methanol / 24 h / 0 °C

With disodium hydrogenphosphate; sodium amalgam; tetrabutyl ammonium fluoride; In tetrahydrofuran; methanol;

DOI:10.1016/S0040-4020(01)00537-3

upstream raw materials:

(2S)-1-O-benzylglycerol-2,3-bis(trifluoromethanesulfonate)

Downstream raw materials:

(2S,5S)-1-tert-butoxycarbonyl-2-hydroxymethyl-3-phenylsulfonyl-5-benzyloxy-methyl pyrrolidine

(2S,5R)-1-tert-butoxycarbonyl-5-hydroxymethyl-2-benzyloxymethyl pyrrolidine

(2S,5R)-1-tert-butoxycarbonyl-2-hydroxymethyl-5-(1'-hydroxy-1'-methylethyl)-pyrrolidine

(2S,5R)-1-tert-butoxycarbonyl-2-benzyloxymethyl-5-methoxycarbonyl-pyrrolidine