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

Base Information

Chemical Name:(1R,2S,3S,5R,7aR)-1,2-dibenzyloxy-3-tert-butyldiphenylsilyloxymethyl-5-methylpyrrolizidine
CAS No.:900780-91-8
Molecular Formula:C₃₉H₄₇NO₃Si
Molecular Weight:605.893
Hs Code.:

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

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Chemical Property of (1R,2S,3S,5R,7aR)-1,2-dibenzyloxy-3-tert-butyldiphenylsilyloxymethyl-5-methylpyrrolizidine

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Technology Process of (1R,2S,3S,5R,7aR)-1,2-dibenzyloxy-3-tert-butyldiphenylsilyloxymethyl-5-methylpyrrolizidine

There total 4 articles about (1R,2S,3S,5R,7aR)-1,2-dibenzyloxy-3-tert-butyldiphenylsilyloxymethyl-5-methylpyrrolizidine 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: 52.0%

: 900780-90-7
4-[(3E,2'R,3'R,4'S,5'S)-3',4'-dibenzyloxy-N-benzyloxycarbonyl-5'-O-tert-butyldiphenylsilyloxymethylpyrrolidin-2'-yl]but-3-en-2-one

: 900780-91-8
(1R,2S,3S,5R,7aR)-1,2-dibenzyloxy-3-tert-butyldiphenylsilyloxymethyl-5-methylpyrrolizidine

Guidance literature:: With hydrogen; palladium on activated charcoal; In methanol; for 18h; under 3102.89 Torr;
DOI:10.1016/j.tet.2006.04.003

Reference yield:

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

: 900780-91-8
(1R,2S,3S,5R,7aR)-1,2-dibenzyloxy-3-tert-butyldiphenylsilyloxymethyl-5-methylpyrrolizidine

Guidance literature:: Multi-step reaction with 4 steps

1: 79 percent / K₂CO₃ / acetone / 0.5 h / 20 °C

2: 88 percent / 4 Angstroem molecular sieves; NMO; TPAP / CH₂Cl₂ / 0.25 h / 20 °C

3: 83 percent / toluene / 3 h / 80 °C

4: 52 percent / H₂ / Pd/C / methanol / 18 h / 3102.89 Torr

With N-methyl-2-indolinone; tetrapropylammonium perruthennate; 4 A molecular sieve; hydrogen; potassium carbonate; palladium on activated charcoal; In methanol; dichloromethane; acetone; toluene; 3: Wittig reaction;
DOI:10.1016/j.tet.2006.04.003

Reference yield:

: 900780-89-4
(2S,3S,4R,5S)-3,4-Bis-benzyloxy-2-(tert-butyl-diphenyl-silanyloxymethyl)-5-formyl-pyrrolidine-1-carboxylic acid benzyl ester

: 900780-91-8
(1R,2S,3S,5R,7aR)-1,2-dibenzyloxy-3-tert-butyldiphenylsilyloxymethyl-5-methylpyrrolizidine

Guidance literature:: Multi-step reaction with 2 steps

1: 83 percent / toluene / 3 h / 80 °C

2: 52 percent / H₂ / Pd/C / methanol / 18 h / 3102.89 Torr

With hydrogen; palladium on activated charcoal; In methanol; toluene; 1: Wittig reaction;
DOI:10.1016/j.tet.2006.04.003