(1S,2S,5R,6R,7R,7aR)-6,7-bis(benzyloxy)-5-(hydroxymethyl)hexahydro-1H-pyrrolizine-1,2-diol

Base Information

Chemical Name:(1S,2S,5R,6R,7R,7aR)-6,7-bis(benzyloxy)-5-(hydroxymethyl)hexahydro-1H-pyrrolizine-1,2-diol
CAS No.:861872-87-9
Molecular Formula:C₂₂H₂₇NO₅
Molecular Weight:385.46
Hs Code.:

Synonyms:(1S,2S,5R,6R,7R,7aR)-6,7-bis(benzyloxy)-5-(hydroxymethyl)hexahydro-1H-pyrrolizine-1,2-diol

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Chemical Property of (1S,2S,5R,6R,7R,7aR)-6,7-bis(benzyloxy)-5-(hydroxymethyl)hexahydro-1H-pyrrolizine-1,2-diol

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Technology Process of (1S,2S,5R,6R,7R,7aR)-6,7-bis(benzyloxy)-5-(hydroxymethyl)hexahydro-1H-pyrrolizine-1,2-diol

There total 9 articles about (1S,2S,5R,6R,7R,7aR)-6,7-bis(benzyloxy)-5-(hydroxymethyl)hexahydro-1H-pyrrolizine-1,2-diol 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: 95.0%

: 861872-86-8
(1R,2R,5R,6R,7R,7aR)-1,2-dibenzyloxy-3-tert-butyldiphenylsilyloxymethyl-6,7-dihydroxypyrrolizidine

: 861872-87-9
(1S,2S,5R,6R,7R,7aR)-6,7-bis(benzyloxy)-5-(hydroxymethyl)hexahydro-1H-pyrrolizine-1,2-diol

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 3h; Heating;
DOI:10.1016/j.tet.2005.05.004

Reference yield:

: 1204748-28-6
(1aR,4R,5R,6R,6aS,6bS)-5,6-bis(benzyloxy)-4-((tertbutyldimethylsilyloxy)methyl)hexahydro-1aH-oxireno[2,3-a]pyrrolizine

: 861872-87-9
(1S,2S,5R,6R,7R,7aR)-6,7-bis(benzyloxy)-5-(hydroxymethyl)hexahydro-1H-pyrrolizine-1,2-diol

: 861872-84-6
(1R,2R,5R,6R,7R,7aR)-6,7-bis(benzyloxy)-5-(hydroxymethyl)hexahydro-1H-pyrrolizine-1,2-diol

Guidance literature:: (1aR,4R,5R,6R,6aS,6bS)-5,6-bis(benzyloxy)-4-((tertbutyldimethylsilyloxy)methyl)hexahydro-1aH-oxireno[2,3-a]pyrrolizine; With sodium hydrogen sulfate; In dichloromethane; for 48h; Inert atmosphere; Reflux;

With water; In dichloromethane; at 20 ℃; for 1h; optical yield given as %de;
DOI:10.1021/jo902355p

Reference yield:

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

: 861872-87-9
(1S,2S,5R,6R,7R,7aR)-6,7-bis(benzyloxy)-5-(hydroxymethyl)hexahydro-1H-pyrrolizine-1,2-diol

Guidance literature:: Multi-step reaction with 6 steps

1.1: 4.9 g / CH₂Cl₂ / 48 h / 20 °C

2.1: 58 percent / N-methylmorpholine; O-(4-chlorobenzoyl)hydroquinine; OsO₄ / acetone; H₂O / 48 h / 20 °C

3.1: hydrogen / Pd/C / methanol / 3 h / 20 °C

4.1: 1.14 g / MeONa / methanol / 2 h / 20 °C

5.1: H₃B*SMe₂ / tetrahydrofuran / 4 h / 20 °C

5.2: 89 percent / MeOH / 3 h / Heating

6.1: 95 percent / n-Bu₄N⁽¹⁺⁾*F^(1-) / tetrahydrofuran / 3 h / Heating

With 4-methyl-morpholine; osmium(VIII) oxide; dimethylsulfide borane complex; tetrabutyl ammonium fluoride; hydrogen; sodium methylate; (1R)-((1S,4S,5R)-5-ethylquinuclidin-2-yl)(6-methoxyquinolin-4-yl)methyl 4-chlorobenzoate; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; water; acetone;
DOI:10.1016/j.tet.2005.05.004