benzyl 2-O-allyl-3,4-di-O-benzyl-6-O-(p-toluenesulfonyl)-α-D-mannopyranoside

Base Information

• Chemical Name: benzyl 2-O-allyl-3,4-di-O-benzyl-6-O-(p-toluenesulfonyl)-α-D-mannopyranoside
• CAS No.: 86342-13-4
• Molecular Formula: C₃₇H₄₀O₈S
• Molecular Weight: 644.786
• Mol file: 86342-13-4.mol

Synonyms:benzyl 2-O-allyl-3,4-di-O-benzyl-6-O-(p-toluenesulfonyl)-α-D-mannopyranoside

Chemical Property of benzyl 2-O-allyl-3,4-di-O-benzyl-6-O-(p-toluenesulfonyl)-α-D-mannopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzyl 2-O-allyl-3,4-di-O-benzyl-6-O-(p-toluenesulfonyl)-α-D-mannopyranoside

There total 4 articles about benzyl 2-O-allyl-3,4-di-O-benzyl-6-O-(p-toluenesulfonyl)-α-D-mannopyranoside 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: 80.4%

benzyl 2-O-allyl-3,4-di-O-benzyl-α-D-mannopyranoside (86353-43-7) + p-toluenesulfonyl chloride (98-59-9) → benzyl 2-O-allyl-3,4-di-O-benzyl-6-O-(p-toluenesulfonyl)-α-D-mannopyranoside (86342-13-4)

Guidance literature:

In pyridine; at 0 - 25 ℃; for 49h;

DOI:10.1016/0040-4020(82)80083-5

Reference yield:

benzyl 2-O-allyl-3-O-benzyl-4,6-O-benzylidene-α-D-mannopyranoside (86342-12-3) → benzyl 2-O-allyl-3,4-di-O-benzyl-6-O-(p-toluenesulfonyl)-α-D-mannopyranoside (86342-13-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 88.9 percent / LiALH₄, AlCl₃ / diethyl ether; CH₂Cl₂ / 1.5 h / Heating

2: 80.4 percent / pyridine / 49 h / 0 - 25 °C

With lithium aluminium tetrahydride; aluminium trichloride; In pyridine; diethyl ether; dichloromethane;

DOI:10.1016/0040-4020(82)80083-5

Reference yield:

benzyl 3-O-benzyl-4,6-O-benzylidene-α-D-mannopyranoside (42926-92-1,42926-93-2,62774-16-7,65925-93-1,65925-97-5,70144-60-4,73366-73-1,78780-60-6,86833-19-4,117895-06-4) → benzyl 2-O-allyl-3,4-di-O-benzyl-6-O-(p-toluenesulfonyl)-α-D-mannopyranoside (86342-13-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 84.2 percent / NaH / dimethylformamide / 17 h

2: 88.9 percent / LiALH₄, AlCl₃ / diethyl ether; CH₂Cl₂ / 1.5 h / Heating

3: 80.4 percent / pyridine / 49 h / 0 - 25 °C

With lithium aluminium tetrahydride; aluminium trichloride; sodium hydride; In pyridine; diethyl ether; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/0040-4020(82)80083-5

upstream raw materials:

benzyl 2-O-allyl-3,4-di-O-benzyl-α-D-mannopyranoside

p-toluenesulfonyl chloride

benzyl 2-O-allyl-3-O-benzyl-4,6-O-benzylidene-α-D-mannopyranoside

benzyl exo-2,3:4,6-di-O-benzylidene-α-D-mannopyranoside

Downstream raw materials:

benzyl 3,4-di-O-benzyl-α-D-rhamnopyranoside

benzyl 2-O-allyl-3,4-di-O-benzyl-α-D-rhamnopyranoside