(3aS,5R,6R,7S,7aS)-6,7-Bis-benzyloxy-5-benzyloxymethyl-2-iodomethyl-hexahydro-furo[3,2-b]pyran

Base Information

• Chemical Name: (3aS,5R,6R,7S,7aS)-6,7-Bis-benzyloxy-5-benzyloxymethyl-2-iodomethyl-hexahydro-furo[3,2-b]pyran
• CAS No.: 192929-28-5
• Molecular Formula: C₃₀H₃₃IO₅
• Molecular Weight: 600.494
• Mol file: 192929-28-5.mol

Synonyms:(3aS,5R,6R,7S,7aS)-6,7-Bis-benzyloxy-5-benzyloxymethyl-2-iodomethyl-hexahydro-furo[3,2-b]pyran

Chemical Property of (3aS,5R,6R,7S,7aS)-6,7-Bis-benzyloxy-5-benzyloxymethyl-2-iodomethyl-hexahydro-furo[3,2-b]pyran

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3aS,5R,6R,7S,7aS)-6,7-Bis-benzyloxy-5-benzyloxymethyl-2-iodomethyl-hexahydro-furo[3,2-b]pyran

There total 3 articles about (3aS,5R,6R,7S,7aS)-6,7-Bis-benzyloxy-5-benzyloxymethyl-2-iodomethyl-hexahydro-furo[3,2-b]pyran 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: 90.0%

3-(3,4,6-tri-O-benzyl-β-D-glucopyranosyl)-1-propene (161275-25-8) → (3aS,5R,6R,7S,7aS)-6,7-Bis-benzyloxy-5-benzyloxymethyl-2-iodomethyl-hexahydro-furo[3,2-b]pyran (192929-28-5)

Guidance literature:

With sodium azide; Iodine monochloride; In acetonitrile; at -78 - 20 ℃;

DOI:10.1016/S0957-4166(98)00427-3

Reference yield: 72.0%

1-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranos-1-yl)-2-propene (81972-19-2) → (3aS,5R,6R,7S,7aS)-6,7-Bis-benzyloxy-5-benzyloxymethyl-2-iodomethyl-hexahydro-furo[3,2-b]pyran (192929-28-5)

Guidance literature:

With iodine; In dichloromethane; at 0 - 20 ℃; for 5h;

DOI:10.1021/jo970127f

Reference yield:

3,4,6-tri-O-benzyl-D-glucal epoxide (74372-90-0) → (3aS,5R,6R,7S,7aS)-6,7-Bis-benzyloxy-5-benzyloxymethyl-2-iodomethyl-hexahydro-furo[3,2-b]pyran (192929-28-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 60 percent / CuBr*Me₂S / diethyl ether; tetrahydrofuran / 2 h / 0 °C

2: 90 percent / ICl, NaN₃ / acetonitrile / -78 - 20 °C

With sodium azide; copper(I) bromide dimethylsulfide complex; Iodine monochloride; In tetrahydrofuran; diethyl ether; acetonitrile;

DOI:10.1016/S0957-4166(98)00427-3

upstream raw materials:

1-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranos-1-yl)-2-propene

3-(3,4,6-tri-O-benzyl-β-D-glucopyranosyl)-1-propene

3,4,6-tri-O-benzyl-D-glucal epoxide

Downstream raw materials:

1-(3',4',6'-tri-O-benzyl-β-D-mannopyranosyl)prop-2-ene

3-C-(3,4,6-tri-O-benzyl-β-D-arabino-hex-2-ulopyranosyl)propene

(2S,4R,5S,6R)-2-Allyl-4,5-bis-benzyloxy-6-benzyloxymethyl-dihydro-pyran-3-one O-methyl-oxime

1-(2'-azido-3',4',6'-tri-O-benzyl-2'-deoxy-β-D-glucopyranosyl)-2-propene