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

Base Information

• Chemical Name: (2S,3S,4R,5R)-3,4-dibenzyloxy-2'-O-tert-butyldiphenylsilyl-2,5-bis(hydroxymethyl)pyrrolidine
• CAS No.: 872345-55-6
• Molecular Formula: C₃₆H₄₃NO₄Si
• Molecular Weight: 581.827
• Mol file: 872345-55-6.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 2 articles about (2S,3S,4R,5R)-3,4-dibenzyloxy-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: 41.0%

(3S,4R,5R)-3,4-dibenzyloxy-2'-O-tert-butyldiphenylsilyl-2,5-bis(hydroxymethyl)-δ2-pyrroline → (2S,3S,4R,5R)-3,4-dibenzyloxy-2'-O-tert-butyldiphenylsilyl-2,5-bis(hydroxymethyl)pyrrolidine (872345-55-6)

Guidance literature:

With sodium cyanoborohydride; acetic acid; In tetrahydrofuran; for 1h; cooling;

DOI:10.1016/j.tet.2005.09.043

Reference yield:

5-azido-3,4-di-O-benzyl-1-O-tert-butyldiphenylsilyl-5-deoxy-α-D-psicopyranose (872345-49-8) → (2S,3S,4R,5R)-3,4-dibenzyloxy-2'-O-tert-butyldiphenylsilyl-2,5-bis(hydroxymethyl)pyrrolidine (872345-55-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 77 percent / PPh₃ / tetrahydrofuran / 7 h / Heating

2: 41 percent / AcOH; NaCNBH₃ / tetrahydrofuran / 1 h / cooling

With sodium cyanoborohydride; acetic acid; triphenylphosphine; In tetrahydrofuran; 1: Staudinger/aza-Wittig reaction;

DOI:10.1016/j.tet.2005.09.043

Reference yield: 79.0%

(2S,3S,4R,5R)-3,4-dibenzyloxy-2'-O-tert-butyldiphenylsilyl-2,5-bis(hydroxymethyl)pyrrolidine (872345-55-6) + benzyl chloroformate (501-53-1,94274-21-2) → (2S,3S,4R,5R)-3,4-dibenzyloxy-N-benzyloxycarbonyl-2'-O-tert-butyldiphenylsilyl-2,5-bis(hydroxymethyl)pyrrolidine (900780-88-3)

Guidance literature:

With potassium carbonate; In acetone; at 20 ℃; for 0.5h;

DOI:10.1016/j.tet.2006.04.003

upstream raw materials:

5-azido-3,4-di-O-benzyl-1-O-tert-butyldiphenylsilyl-5-deoxy-α-D-psicopyranose

Downstream raw materials:

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

(1S,2R,3R,5S,7aS)-3'-benzoyloxymethyl-1,2-dibenzyloxy-5-methylpyrrolizidine

(2R,3R,4S,5R)-2-Benzoyloxymethyl-3,4-bis-benzyloxy-5-formyl-pyrrolidine-1-carboxylic acid benzyl ester

(2R,3R,4S,5S)-2'-O-benzoyl-3,4-dibenzyloxy-N-benzyloxycarbonyl-2,5-bis(hydroxymethyl)pyrrolidine