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

Base Information

• Chemical Name: (2S,3S,4R,5R)-3,4-dibenzyloxy-N-benzyloxycarbonyl-2'-O-tert-butyldiphenylsilyl-2,5-bis(hydroxymethyl)pyrrolidine
• CAS No.: 900780-88-3
• Molecular Formula: C₄₄H₄₉NO₆Si
• Molecular Weight: 715.962

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

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

Chemical Property:

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

There total 2 articles about (2S,3S,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: 86.0%

(2R,3R,4S,5S)-2-acetyloxymethyl-3,4-dibenzyloxy-N-benzyloxycarbonyl-5-tert-butyldiphenylsilyloxymethylpyrrolidine (1037673-71-4) → (2S,3S,4R,5R)-3,4-dibenzyloxy-N-benzyloxycarbonyl-2'-O-tert-butyldiphenylsilyl-2,5-bis(hydroxymethyl)pyrrolidine (900780-88-3)

Guidance literature:

With methanol; sodium methylate; at 20 ℃; for 12h;

DOI:10.1016/j.tet.2008.03.089

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

Reference yield: 95.0%

(2S,3S,4R,5R)-3,4-dibenzyloxy-N-benzyloxycarbonyl-2'-O-tert-butyldiphenylsilyl-2,5-bis(hydroxymethyl)pyrrolidine (900780-88-3) + benzoyl chloride (98-88-4) → (2R,3R,4S,5S)-2'-O-benzoyl-3,4-dibenzyloxy-N-benzyloxycarbonyl-5'-O-tert-butyldiphenylsilyl-2,5-bis(hydroxymethyl)pyrrolidine (900780-92-9)

Guidance literature:

With dmap; TEA; In dichloromethane; at 20 ℃; for 20h;

DOI:10.1016/j.tet.2006.04.003

upstream raw materials:

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

benzyl chloroformate

(2R,3R,4S,5S)-2-acetyloxymethyl-3,4-dibenzyloxy-N-benzyloxycarbonyl-5-tert-butyldiphenylsilyloxymethylpyrrolidine

Downstream raw materials:

(2S,3S,4R,5S)-3,4-Bis-benzyloxy-2-(tert-butyl-diphenyl-silanyloxymethyl)-5-formyl-pyrrolidine-1-carboxylic acid benzyl ester

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

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