(2R,3S,4R,5R)-3,4-bis(benzyloxy)-N-(tert-butyloxycarbonyl)-2'-O-(tert-butyldiphenylsilyl)-2,5-bis(hydroxymethyl)pyrrolidine

Base Information

• Chemical Name: (2R,3S,4R,5R)-3,4-bis(benzyloxy)-N-(tert-butyloxycarbonyl)-2'-O-(tert-butyldiphenylsilyl)-2,5-bis(hydroxymethyl)pyrrolidine
• CAS No.: 1006295-21-1
• Molecular Formula: C₄₁H₅₁NO₆Si
• Molecular Weight: 681.945

Synonyms:(2R,3S,4R,5R)-3,4-bis(benzyloxy)-N-(tert-butyloxycarbonyl)-2'-O-(tert-butyldiphenylsilyl)-2,5-bis(hydroxymethyl)pyrrolidine

Chemical Property of (2R,3S,4R,5R)-3,4-bis(benzyloxy)-N-(tert-butyloxycarbonyl)-2'-O-(tert-butyldiphenylsilyl)-2,5-bis(hydroxymethyl)pyrrolidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

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Technology Process of (2R,3S,4R,5R)-3,4-bis(benzyloxy)-N-(tert-butyloxycarbonyl)-2'-O-(tert-butyldiphenylsilyl)-2,5-bis(hydroxymethyl)pyrrolidine

There total 2 articles about (2R,3S,4R,5R)-3,4-bis(benzyloxy)-N-(tert-butyloxycarbonyl)-2'-O-(tert-butyldiphenylsilyl)-2,5-bis(hydroxymethyl)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: 100.0%

(2R,3S,4R,5R)-3,4-bis(benzyloxy)-2'-O-(tert-butyldiphenylsilyl)-2,5-bis(hydroxymethyl)pyrrolidine (872345-56-7) + di-tert-butyl dicarbonate (24424-99-5) → (2R,3S,4R,5R)-3,4-bis(benzyloxy)-N-(tert-butyloxycarbonyl)-2'-O-(tert-butyldiphenylsilyl)-2,5-bis(hydroxymethyl)pyrrolidine (1006295-21-1)

Guidance literature:

With triethylamine; In dichloromethane; at 20 ℃;

DOI:10.1002/ejoc.200700820

Reference yield: 100.0%

(2R,3S,4R,5R)-3,4-bis(benzyloxy)-2'-O-(tert-butyldiphenylsilyl)-2,5-bis(hydroxymethyl)pyrrolidine (872345-56-7) + 2,2-dimethylpropanoic anhydride (1538-75-6) → (2R,3S,4R,5R)-3,4-bis(benzyloxy)-N-(tert-butyloxycarbonyl)-2'-O-(tert-butyldiphenylsilyl)-2,5-bis(hydroxymethyl)pyrrolidine (1006295-21-1)

Guidance literature:

With triethylamine; In dichloromethane; at 20 ℃; chemoselective reaction; Cooling with ice;

DOI:10.1016/j.tet.2010.03.049

Reference yield: 85.0%

(2R,3S,4R,5R)-3,4-bis(benzyloxy)-N-(tert-butyloxycarbonyl)-2'-O-(tert-butyldiphenylsilyl)-2,5-bis(hydroxymethyl)pyrrolidine (1006295-21-1) + acetic anhydride (108-24-7) → (2R,3R,4S,5R)-2-acetyloxymethyl-3,4-dibenzyloxy-N-tert-butyloxycarbonyl-5-tert-butyldiphenylsilyloxymethylpyrrolidine

Guidance literature:

With pyridine; dmap; at 20 ℃;

DOI:10.1016/j.tet.2008.03.089

upstream raw materials:

(2R,3S,4R,5R)-3,4-bis(benzyloxy)-2'-O-(tert-butyldiphenylsilyl)-2,5-bis(hydroxymethyl)pyrrolidine

di-tert-butyl dicarbonate

2,2-dimethylpropanoic anhydride

Downstream raw materials:

(2R,3R,4S,5R)-2'-O-benzoyl-3,4-bis(benzyloxy)-N-(tert-butyloxycarbonyl)-5'-O-(tert-butyldiphenylsilyl)-2,5-bis(hydroxymethyl)pyrrolidine

(2R,3S,4R,5S)-3,4-bis(benzyloxy)-1-(tert-butoxycarbonyl)-2-[(tert-butyldiphenylsilyloxy)methyl]-5-(iodomethyl)pyrrolidine

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