(E)-4-[(2'R,3'R,4'R,5'R)-3',4'-dibenzyloxy-N-benzyloxycarbonyl-5'-tert-butyldiphenylsilyloximethylpyrrolidin-2'-yl]but-3-en-2-one

Base Information

Chemical Name:(E)-4-[(2'R,3'R,4'R,5'R)-3',4'-dibenzyloxy-N-benzyloxycarbonyl-5'-tert-butyldiphenylsilyloximethylpyrrolidin-2'-yl]but-3-en-2-one
CAS No.:1361194-00-4
Molecular Formula:C₄₇H₅₁NO₆Si
Molecular Weight:754.011
Hs Code.:

Synonyms:(E)-4-[(2'R,3'R,4'R,5'R)-3',4'-dibenzyloxy-N-benzyloxycarbonyl-5'-tert-butyldiphenylsilyloximethylpyrrolidin-2'-yl]but-3-en-2-one

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Chemical Property of (E)-4-[(2'R,3'R,4'R,5'R)-3',4'-dibenzyloxy-N-benzyloxycarbonyl-5'-tert-butyldiphenylsilyloximethylpyrrolidin-2'-yl]but-3-en-2-one

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Technology Process of (E)-4-[(2'R,3'R,4'R,5'R)-3',4'-dibenzyloxy-N-benzyloxycarbonyl-5'-tert-butyldiphenylsilyloximethylpyrrolidin-2'-yl]but-3-en-2-one

There total 1 articles about (E)-4-[(2'R,3'R,4'R,5'R)-3',4'-dibenzyloxy-N-benzyloxycarbonyl-5'-tert-butyldiphenylsilyloximethylpyrrolidin-2'-yl]but-3-en-2-one 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:

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

: 1439-36-7
1-triphenylphosphoranylidene-2-propanone

: 1361194-00-4
(E)-4-[(2'R,3'R,4'R,5'R)-3',4'-dibenzyloxy-N-benzyloxycarbonyl-5'-tert-butyldiphenylsilyloximethylpyrrolidin-2'-yl]but-3-en-2-one

Guidance literature:: In toluene; for 24h; Reflux;
DOI:10.1002/ejoc.201101126

Reference yield: 37.0%

: 1361194-00-4
(E)-4-[(2'R,3'R,4'R,5'R)-3',4'-dibenzyloxy-N-benzyloxycarbonyl-5'-tert-butyldiphenylsilyloximethylpyrrolidin-2'-yl]but-3-en-2-one

: 1361194-02-6
(2R,3R,4R,5R)-3,4-dibenzyloxy-N-benzyloxycarbonyl-2-tert-butyldiphenylsilyloxymethyl-5-[(1'S,2'R)-1'-2'-dihydroxy-3'-oxobutyl]pyrrolidine

: 1361194-04-8
(2R,3R,4R,5R)-3,4-dibenzyloxy-N-benzyloxycarbonyl-2-tert-butyldiphenylsilyloxymethyl-5-[(1'R,2'S)-1'-2'-dihydroxy-3'-oxobutyl]pyrrolidine

Guidance literature:: With osmium(VIII) oxide; water; 4-methylmorpholine N-oxide; In acetone; at 20 ℃; for 20h; optical yield given as %de;
DOI:10.1002/ejoc.201101126

Reference yield:

: 1361194-00-4
(E)-4-[(2'R,3'R,4'R,5'R)-3',4'-dibenzyloxy-N-benzyloxycarbonyl-5'-tert-butyldiphenylsilyloximethylpyrrolidin-2'-yl]but-3-en-2-one

: 1361194-08-2
(1R,2R,3R,5S,6S,7S,7aR)-1,2-dibenzyloxy-6,7-dihydroxy-3-hydroxymethyl-5-methylpyrrolizidine

Guidance literature:: Multi-step reaction with 3 steps

1: osmium(VIII) oxide; water; 4-methylmorpholine N-oxide / acetone / 20 h / 20 °C

2: palladium 10% on activated carbon; hydrogen / methanol / 3102.97 Torr

3: tetrabutyl ammonium fluoride; water / tetrahydrofuran / 16 h / 50 °C

With osmium(VIII) oxide; palladium 10% on activated carbon; tetrabutyl ammonium fluoride; water; hydrogen; 4-methylmorpholine N-oxide; In tetrahydrofuran; methanol; acetone;
DOI:10.1002/ejoc.201101126