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

Base Information

Chemical Name:(1R,2R,3R,5S,6S,7S,7aR)-1,2-dibenzyloxy-6,7-dihydroxy-3-hydroxymethyl-5-methylpyrrolizidine
CAS No.:1361194-08-2
Molecular Formula:C₂₃H₂₉NO₅
Molecular Weight:399.487
Hs Code.:

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

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

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

There total 5 articles about (1R,2R,3R,5S,6S,7S,7aR)-1,2-dibenzyloxy-6,7-dihydroxy-3-hydroxymethyl-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: 94.0%

: 1361194-06-0
(1R,2R,3R,5S,6S,7S,7aR)-1,2-dibenzyloxy-3-tert-butyldiphenylsilyloxymethyl-6,7-dihydroxy-5-methylpyrrolizidine

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

Guidance literature:: With tetrabutyl ammonium fluoride; water; In tetrahydrofuran; at 50 ℃; for 16h;
DOI:10.1002/ejoc.201101126

Reference yield:

: 861872-76-6
(2R,3R,4R,5R)-3,4-dibenzyloxy-N-benzyloxycarbonyl-2'-O-tert-butyldiphenylsilyl-2,5-bis(hydroxymethyl)pyrrolidine

: 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 5 steps

1: tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide / dichloromethane / 1 h / 20 °C / Molecular sieve

2: toluene / 24 h / Reflux

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

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

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

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

Reference yield:

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

: 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 4 steps

1: toluene / 24 h / Reflux

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

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

4: 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; toluene;
DOI:10.1002/ejoc.201101126