(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
• Mol file: 1361226-80-3.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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%

(1S,2R,3R,6R,7aR)-1,2-bis(benzyloxy)-3-[(benzyloxy)methyl]-6-(methylsulfonyloxy)-hexahydro-1H-pyrrolizine (1361226-79-0) → (1S,2R,3R,7aR)-1,2-bis(benzyloxy)-3-[(benzyloxy)methyl]hexahydro-1H-pyrrolizine (1361226-80-3)

Guidance literature:

With diisobutylaluminium hydride; In dichloromethane; toluene; at 0 ℃; Inert atmosphere; Reflux;

DOI:10.1002/ejoc.201101096

Reference yield:

(2R,3R,4S)-3,4-bis(benzyloxy)-2-[(benzyloxy)methyl]-3,4-dihydro-2H-pyrrole 1-oxide (213617-02-8) → (1S,2R,3R,7aR)-1,2-bis(benzyloxy)-3-[(benzyloxy)methyl]hexahydro-1H-pyrrolizine (1361226-80-3)

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:

tert-butyl (2R,3aR,4S,5R,6R)-4,5-bis(benzyloxy)-6-[(benzyloxy)methyl]hexahydropyrrolo[1,2-b]isoxazole-2-carboxylate (1361226-69-8) → (1S,2R,3R,7aR)-1,2-bis(benzyloxy)-3-[(benzyloxy)methyl]hexahydro-1H-pyrrolizine (1361226-80-3)

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

upstream raw materials:

(1S,2R,3R,6R,7aR)-1,2-bis(benzyloxy)-3-(benzyloxymethyl)-6-hydroxyhexahydro-5H-pyrrolizin-5-one

(1S,2R,3R,6R,7aR)-1,2-bis(benzyloxy)-3-[(benzyloxy)methyl]-6-hydroxyhexahydro-1H-pyrrolizine

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

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