O-(3,4,6-tri-O-benzyl-β-D-glucopyranosyl)-(1<*>3)-1,5-anhydro-4,6-O-benzylidene-2-deoxy-D-arabino-hex-1-enitol

Base Information

• Chemical Name: O-(3,4,6-tri-O-benzyl-β-D-glucopyranosyl)-(1<*>3)-1,5-anhydro-4,6-O-benzylidene-2-deoxy-D-arabino-hex-1-enitol
• CAS No.: 135192-34-6
• Molecular Formula: C₄₀H₄₂O₉
• Molecular Weight: 666.768
• Mol file: 135192-34-6.mol

Synonyms:O-(3,4,6-tri-O-benzyl-β-D-glucopyranosyl)-(1<*>3)-1,5-anhydro-4,6-O-benzylidene-2-deoxy-D-arabino-hex-1-enitol

Chemical Property of O-(3,4,6-tri-O-benzyl-β-D-glucopyranosyl)-(1<*>3)-1,5-anhydro-4,6-O-benzylidene-2-deoxy-D-arabino-hex-1-enitol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of O-(3,4,6-tri-O-benzyl-β-D-glucopyranosyl)-(1<*>3)-1,5-anhydro-4,6-O-benzylidene-2-deoxy-D-arabino-hex-1-enitol

There total 6 articles about O-(3,4,6-tri-O-benzyl-β-D-glucopyranosyl)-(1<*>3)-1,5-anhydro-4,6-O-benzylidene-2-deoxy-D-arabino-hex-1-enitol 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:

4,6-O-benzylidene-D-glucal (63598-36-7,167074-37-5) + 3,4,6-tri-O-benzyl-β-D-glucopyranosyl 1-diethyldithiocarbamate (1380516-32-4) → 3,4,6-tri-O-benzyl-α-D-glucopyranosyl-(1->3)-4,6-O-benzylidene-D-glucal (1380673-17-5) + O-(3,4,6-tri-O-benzyl-β-D-glucopyranosyl)-(1<*>3)-1,5-anhydro-4,6-O-benzylidene-2-deoxy-D-arabino-hex-1-enitol (135192-34-6)

Guidance literature:

3,4,6-tri-O-benzyl-β-D-glucopyranosyl 1-diethyldithiocarbamate; With 2,4,6-tri-tert-butylpyrimidine; In dichloromethane; 1,2-dichloro-ethane; at 20 ℃; for 1h; Molecular sieve;

With copper(I) triflate benzene complex; In dichloromethane; 1,2-dichloro-ethane; at -50 ℃; for 0.166667h;

4,6-O-benzylidene-D-glucal; In dichloromethane; 1,2-dichloro-ethane; at -50 - -30 ℃; for 15.8333h; optical yield given as %de; stereoselective reaction;

DOI:10.1021/ol301349w

Reference yield:

3,4,6-tri-O-benzyl-D-glucal (55628-54-1) → O-(3,4,6-tri-O-benzyl-β-D-glucopyranosyl)-(1<*>3)-1,5-anhydro-4,6-O-benzylidene-2-deoxy-D-arabino-hex-1-enitol (135192-34-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 3,3-dimethyldioxirane / CH₂Cl₂ / 0.25 h / 0 °C

2: ZnCl₂ / tetrahydrofuran; diethyl ether / 1.) -78 deg C to 25 deg C, 2.) 25 deg C, overnight

With 3,3-dimethyldioxirane; zinc(II) chloride; In tetrahydrofuran; diethyl ether; dichloromethane;

DOI:10.1021/jo00018a047

Reference yield:

4,6-O-benzylidene-D-glucal (63598-36-7,167074-37-5) + 3,4,6-tri-O-benzyl-β-D-glucopyranosyl 1-diphenyldithiocarbamate (1563178-02-8) → 3,4,6-tri-O-benzyl-α-D-glucopyranosyl-(1->3)-4,6-O-benzylidene-D-glucal (1380673-17-5) + O-(3,4,6-tri-O-benzyl-β-D-glucopyranosyl)-(1<*>3)-1,5-anhydro-4,6-O-benzylidene-2-deoxy-D-arabino-hex-1-enitol (135192-34-6)

Guidance literature:

3,4,6-tri-O-benzyl-β-D-glucopyranosyl 1-diphenyldithiocarbamate; In dichloromethane; 1,2-dichloro-ethane; at 20 ℃; for 1h; Inert atmosphere; Molecular sieve;

4,6-O-benzylidene-D-glucal; With copper(II) bis(trifluoromethanesulfonate); In dichloromethane; 1,2-dichloro-ethane; at -50 - -30 ℃; diastereoselective reaction; Inert atmosphere; Molecular sieve;

DOI:10.1021/jo500032k

upstream raw materials:

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

4,6-O-benzylidene-D-glucal

3,4,6-tri-O-benzyl-β-D-glucopyranosyl 1-diethyldithiocarbamate

3,4,6-tri-O-benzyl-β-D-glucopyranosyl 1-diphenyldithiocarbamate

Downstream raw materials:

O-(3,4,6-tri-O-benzyl-2-O-<(pentafluorophenoxy)thiocarbonyl>-β-D-glucosyl)-(1<*>3)-1,5-anhydro-4,6-O-benzylidene-2-deoxy-D-arabino-hex-1-enopyranose

O-(3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl)-(1<*>3)-1,5-anhydro-4,6-di-O-benzylidene-2-deoxy-D-arabino-hex-1-enopyranose