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

Base Information

• Chemical Name: tert-butyl (2R,3aR,4S,5R,6R)-4,5-bis(benzyloxy)-6-[(benzyloxy)methyl]hexahydropyrrolo[1,2-b]isoxazole-2-carboxylate
• CAS No.: 1361226-69-8
• Molecular Formula: C₃₃H₃₉NO₆
• Molecular Weight: 545.676
• Mol file: 1361226-69-8.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 1 articles about tert-butyl (2R,3aR,4S,5R,6R)-4,5-bis(benzyloxy)-6-[(benzyloxy)methyl]hexahydropyrrolo[1,2-b]isoxazole-2-carboxylate 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: 50.0%

tert-Butyl acrylate (1663-39-4,25232-27-3) + (2R,3R,4S)-3,4-bis(benzyloxy)-2-[(benzyloxy)methyl]-3,4-dihydro-2H-pyrrole 1-oxide (213617-02-8) → tert-butyl (2R,3aR,4S,5R,6R)-4,5-bis(benzyloxy)-6-[(benzyloxy)methyl]hexahydropyrrolo[1,2-b]isoxazole-2-carboxylate (1361226-69-8) + tert-butyl (2S,3aS,4S,5R,6R)-4,5-bis(benzyloxy)-6-[(benzyloxy)methyl]hexahydropyrrolo[1,2-b]isoxazole-2-carboxylate (1361226-68-7)

Guidance literature:

In dichloromethane; at 20 ℃; for 72h; optical yield given as %ee; Inert atmosphere;

DOI:10.1002/ejoc.201101096

Reference yield: 92.0%

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,6R,7aR)-1,2-bis(benzyloxy)-3-(benzyloxymethyl)-6-hydroxyhexahydro-5H-pyrrolizin-5-one (1361226-76-7)

Guidance literature:

tert-butyl (2R,3aR,4S,5R,6R)-4,5-bis(benzyloxy)-6-[(benzyloxy)methyl]hexahydropyrrolo[1,2-b]isoxazole-2-carboxylate; With acetic acid; zinc; In water; for 24h; Reflux;

In methanol; at 20 ℃; for 10h;

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,6R,7aR)-1,2-bis(benzyloxy)-3-[(benzyloxy)methyl]-6-hydroxyhexahydro-1H-pyrrolizine (1361226-77-8)

Guidance literature:

Multi-step reaction with 2 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

With lithium aluminium tetrahydride; acetic acid; zinc; In tetrahydrofuran; water;

DOI:10.1002/ejoc.201101096

upstream raw materials:

tert-Butyl acrylate

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

Downstream 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

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