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

Base Information

• Chemical Name: (2R,3R,4R,5R)-3,4-dibenzyloxy-N-benzyloxycarbonyl-2'-O-tert-butyldiphenylsilyl-2,5-bis(hydroxymethyl)pyrrolidine
• CAS No.: 861872-76-6
• Molecular Formula: C₄₄H₄₉NO₆Si
• Molecular Weight: 715.962
• Mol file: 861872-76-6.mol

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

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

There total 3 articles about (2R,3R,4R,5R)-3,4-dibenzyloxy-N-benzyloxycarbonyl-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: 93.0%

benzyl chloroformate (501-53-1,94274-21-2) + (2R,3R,4R,5R)-3,4-dibenzyloxy-2'-O-tert-butyldiphenylsilyl-2,5-bis(hydroxymethyl)pyrrolidine (487040-55-1) → (2R,3R,4R,5R)-3,4-dibenzyloxy-N-benzyloxycarbonyl-2'-O-tert-butyldiphenylsilyl-2,5-bis(hydroxymethyl)pyrrolidine (861872-76-6)

Guidance literature:

With potassium carbonate; In acetone; at 20 ℃; for 3h;

DOI:10.1016/j.tet.2005.05.004

Reference yield: 64.0%

(3R,4R,5R)-3,4-dibenzyloxy-2'-O-tert-butyldiphenylsilyl-2,5-bis(hydroxymethyl)pyrrolidine + benzyl chloroformate (501-53-1,94274-21-2) → (2R,3R,4R,5R)-3,4-dibenzyloxy-N-benzyloxycarbonyl-2'-O-tert-butyldiphenylsilyl-2,5-bis(hydroxymethyl)pyrrolidine (861872-76-6) + (2S,3R,4R,5R)-3,4-dibenzyloxy-N-benzyloxycarbonyl-2'-O-tert-butyldiphenylsilyl-2,5-bis(hydroxymethyl)pyrrolidine (909192-15-0)

Guidance literature:

With potassium carbonate; In acetone; at 20 ℃; for 6h;

DOI:10.1080/07328300600735181

Reference yield:

5-azido-3,4-di-O-benzyl-1-O-tert-butyldiphenylsilyl-5-deoxy-β-D-fructopyranose (487040-51-7) → (2R,3R,4R,5R)-3,4-dibenzyloxy-N-benzyloxycarbonyl-2'-O-tert-butyldiphenylsilyl-2,5-bis(hydroxymethyl)pyrrolidine (861872-76-6)

Guidance literature:

Multi-step reaction with 2 steps

1: H₂; Raney-nickel / methanol; H₂O / 12 h / 3102.89 Torr

2: 64 percent / K₂CO₃ / acetone / 6 h / 20 °C

With hydrogen; nickel; potassium carbonate; In methanol; water; acetone;

DOI:10.1080/07328300600735181

upstream raw materials:

benzyl chloroformate

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

5-azido-3,4-di-O-benzyl-1-O-tert-butyldiphenylsilyl-5-deoxy-β-D-fructopyranose

Downstream raw materials:

(1R,2R,3R,5S,6S,7S,7aR)-1,2-dibenzyloxy-3-tert-butyldiphenylsilyloxymethyl-6,7-dihydroxy-5-methylpyrrolizidine

(1R,2R,3R,5S,6S,7S,7aR)-1,2-dibenzyloxy-6,7-dihydroxy-3-hydroxymethyl-5-methylpyrrolizidine

(1R,2R,3R,5S,6R,7R,7aR)-1,2-dibenzyloxy-3-tert-butyldiphenylsilyloxymethyl-6,7-dihydroxy-5-methylpyrrolizidine

(1R,2R,3R,5S,6R,7R,7aR)-1,2-dibenzyloxy-6,7-dihydroxy-3-hydroxymethyl-5-methylpyrrolizidine