(1S,2R,3R,7aR)-1,2-bis(benzyloxy)-3-[(benzyloxy)methyl]hexahydro-1H-pyrrolizine

Base Information

Chemical Name:(1S,2R,3R,7aR)-1,2-bis(benzyloxy)-3-[(benzyloxy)methyl]hexahydro-1H-pyrrolizine
CAS No.:1361226-80-3
Molecular Formula:C₂₉H₃₃NO₃
Molecular Weight:443.586
Hs Code.:

Synonyms:(1S,2R,3R,7aR)-1,2-bis(benzyloxy)-3-[(benzyloxy)methyl]hexahydro-1H-pyrrolizine

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Chemical Property of (1S,2R,3R,7aR)-1,2-bis(benzyloxy)-3-[(benzyloxy)methyl]hexahydro-1H-pyrrolizine

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Technology Process of (1S,2R,3R,7aR)-1,2-bis(benzyloxy)-3-[(benzyloxy)methyl]hexahydro-1H-pyrrolizine

There total 5 articles about (1S,2R,3R,7aR)-1,2-bis(benzyloxy)-3-[(benzyloxy)methyl]hexahydro-1H-pyrrolizine 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: 56.0%

: 1361226-79-0
(1S,2R,3R,6R,7aR)-1,2-bis(benzyloxy)-3-[(benzyloxy)methyl]-6-(methylsulfonyloxy)-hexahydro-1H-pyrrolizine

: 1361226-80-3
(1S,2R,3R,7aR)-1,2-bis(benzyloxy)-3-[(benzyloxy)methyl]hexahydro-1H-pyrrolizine

Guidance literature:: With diisobutylaluminium hydride; In dichloromethane; toluene; at 0 ℃; Inert atmosphere; Reflux;
DOI:10.1002/ejoc.201101096

Reference yield:

: 213617-02-8
(2R,3R,4S)-3,4-bis(benzyloxy)-2-[(benzyloxy)methyl]-3,4-dihydro-2H-pyrrole 1-oxide

: 1361226-80-3
(1S,2R,3R,7aR)-1,2-bis(benzyloxy)-3-[(benzyloxy)methyl]hexahydro-1H-pyrrolizine

Guidance literature:: Multi-step reaction with 5 steps

1.1: dichloromethane / 72 h / 20 °C / Inert atmosphere

2.1: acetic acid; zinc / water / 24 h / Reflux

2.2: Ambersep 900 OH / 10 h / 20 °C

3.1: lithium aluminium tetrahydride / tetrahydrofuran / 0 °C / Inert atmosphere; Reflux

4.1: triethylamine / dichloromethane / 0 - 20 °C / Inert atmosphere

5.1: diisobutylaluminium hydride / dichloromethane; toluene / 0 °C / Inert atmosphere; Reflux

With lithium aluminium tetrahydride; diisobutylaluminium hydride; acetic acid; triethylamine; zinc; In tetrahydrofuran; dichloromethane; water; toluene;
DOI:10.1002/ejoc.201101096

Reference yield:

: 1361226-69-8
tert-butyl (2R,3aR,4S,5R,6R)-4,5-bis(benzyloxy)-6-[(benzyloxy)methyl]hexahydropyrrolo[1,2-b]isoxazole-2-carboxylate

: 1361226-80-3
(1S,2R,3R,7aR)-1,2-bis(benzyloxy)-3-[(benzyloxy)methyl]hexahydro-1H-pyrrolizine

Guidance literature:: Multi-step reaction with 4 steps

1.1: acetic acid; zinc / water / 24 h / Reflux

1.2: Ambersep 900 OH / 10 h / 20 °C

2.1: lithium aluminium tetrahydride / tetrahydrofuran / 0 °C / Inert atmosphere; Reflux

3.1: triethylamine / dichloromethane / 0 - 20 °C / Inert atmosphere

4.1: diisobutylaluminium hydride / dichloromethane; toluene / 0 °C / Inert atmosphere; Reflux

With lithium aluminium tetrahydride; diisobutylaluminium hydride; acetic acid; triethylamine; zinc; In tetrahydrofuran; dichloromethane; water; toluene;
DOI:10.1002/ejoc.201101096