methyl (1S,2R,6R,7R,7aR)-6,7-bis(benzyloxy)-5-[(benzyloxy)methyl]-2-hydroxy-3-oxohexahydro-1H-pyrrolizine-1-carboxylate

Base Information

• Chemical Name: methyl (1S,2R,6R,7R,7aR)-6,7-bis(benzyloxy)-5-[(benzyloxy)methyl]-2-hydroxy-3-oxohexahydro-1H-pyrrolizine-1-carboxylate
• CAS No.: 1227870-30-5
• Molecular Formula: C₃₁H₃₃NO₇
• Molecular Weight: 531.606
• Mol file: 1227870-30-5.mol

Synonyms:methyl (1S,2R,6R,7R,7aR)-6,7-bis(benzyloxy)-5-[(benzyloxy)methyl]-2-hydroxy-3-oxohexahydro-1H-pyrrolizine-1-carboxylate

Chemical Property of methyl (1S,2R,6R,7R,7aR)-6,7-bis(benzyloxy)-5-[(benzyloxy)methyl]-2-hydroxy-3-oxohexahydro-1H-pyrrolizine-1-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (1S,2R,6R,7R,7aR)-6,7-bis(benzyloxy)-5-[(benzyloxy)methyl]-2-hydroxy-3-oxohexahydro-1H-pyrrolizine-1-carboxylate

There total 1 articles about methyl (1S,2R,6R,7R,7aR)-6,7-bis(benzyloxy)-5-[(benzyloxy)methyl]-2-hydroxy-3-oxohexahydro-1H-pyrrolizine-1-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:

(2R,3R,4R)-3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-3,4-dihydro-2H-pyrrole 1-oxide (537030-19-6) → methyl (1S,2R,6R,7R,7aR)-6,7-bis(benzyloxy)-5-[(benzyloxy)methyl]-2-hydroxy-3-oxohexahydro-1H-pyrrolizine-1-carboxylate (1227870-30-5)

Guidance literature:

Multi-step reaction with 2 steps

1: dichloromethane

2: zinc; acetic acid / water / 4 h / 50 °C

With acetic acid; zinc; In dichloromethane; water;

DOI:10.1016/j.cclet.2017.06.016

Reference yield: 75.0%

methyl (1S,2R,6R,7R,7aR)-6,7-bis(benzyloxy)-5-[(benzyloxy)methyl]-2-hydroxy-3-oxohexahydro-1H-pyrrolizine-1-carboxylate (1227870-30-5) + 2,3,4,6-tetra-O-benzyl-D-glucopyranose trichloroacetimidate (132201-75-3) → (2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-(1->6)-O-tris(benzyloxy)-7-deoxy-7-methoxycarbonyl-5-oxo-casuarine (1227870-29-2)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In diethyl ether; dichloromethane; at -20 - 20 ℃; Molecular sieve; Inert atmosphere;

DOI:10.1039/b926600c

Reference yield: 75.0%

methyl (1S,2R,6R,7R,7aR)-6,7-bis(benzyloxy)-5-[(benzyloxy)methyl]-2-hydroxy-3-oxohexahydro-1H-pyrrolizine-1-carboxylate (1227870-30-5) + 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl trichloroacetimidate (74808-09-6) → (2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-(1->6)-O-tris(benzyloxy)-7-deoxy-7-methoxycarbonyl-5-oxo-casuarine (1227870-29-2)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In diethyl ether; dichloromethane; at -20 - 20 ℃; for 1h; Inert atmosphere; Molecular sieve;

DOI:10.1002/ejoc.201000632

upstream raw materials:

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

Downstream raw materials:

(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-(1->6)-O-tris(benzyloxy)-7-deoxy-7-methoxycarbonyl-5-oxo-casuarine