Methyl 2-O-Allyl-4,6-O-benzylidene-3-O-(2’,3’,4’,6’-tetra-O-acetyl-α-D-mannopyranosyl)-α-D-mannopyranoside

Base Information

• Chemical Name: Methyl 2-O-Allyl-4,6-O-benzylidene-3-O-(2’,3’,4’,6’-tetra-O-acetyl-α-D-mannopyranosyl)-α-D-mannopyranoside
• CAS No.: 82185-93-1
• Molecular Formula: C₃₁H₄₀O₁₅
• Molecular Weight: 652.65
• Mol file: 82185-93-1.mol

Synonyms:Methyl 2-O-Allyl-4,6-O-benzylidene-3-O-(2’,3’,4’,6’-tetra-O-acetyl-α-D-mannopyranosyl)-α-D-mannopyranoside;Methyl 4,6-O-(PhenylMethylene)-2-O-2-propen-1-yl-3-O-(2,3,4,6-tetra-O-acetyl-α-D-Mannopyranosyl)-α-D-Mannopyranoside

Chemical Property of Methyl 2-O-Allyl-4,6-O-benzylidene-3-O-(2’,3’,4’,6’-tetra-O-acetyl-α-D-mannopyranosyl)-α-D-mannopyranoside

Chemical Property:

• Melting Point: 120°C
• PSA: 169.81000
• LogP: 1.51140
• Solubility.: Chloroform, Dichloromethane, Ethyl Acetate, Methanol

Purity/Quality:

97% ^*data from raw suppliers

Methyl2-O-Allyl-4,6-O-benzylidene-3-O-(2’,3’,4’,6’-tetra-O-acetyl-α-D-mannopyranosyl)-α-D-mannopyranoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Methyl 2-O-Allyl-4,6-O-benzylidene-3-O-(2’,3’,4’,6’-tetra-O-acetyl-α-D-mannopyranosyl)-α-D-mannopyranoside (cas# 82185-93-1) is a compound useful in organic synthesis.

Technology Process of Methyl 2-O-Allyl-4,6-O-benzylidene-3-O-(2’,3’,4’,6’-tetra-O-acetyl-α-D-mannopyranosyl)-α-D-mannopyranoside

There total 5 articles about Methyl 2-O-Allyl-4,6-O-benzylidene-3-O-(2’,3’,4’,6’-tetra-O-acetyl-α-D-mannopyranosyl)-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: 90.0%

methyl 2-O-allyl-4,6-O-benzylidene-α-D-mannopyranoside (81600-89-7) + acetobromomannose (13242-53-0) → methyl 2-O-allyl-4,6-O-benzylidene-3-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-α-D-mannopyranoside (82185-93-1,131614-85-2)

Guidance literature:

With 4 A molecular sieve; mercury(II) cyanide; mercury dibromide; In acetonitrile; for 1h; Ambient temperature;

DOI:10.1016/S0008-6215(82)80004-9

Reference yield: 45.0%

methyl 2-O-allyl-4,6-O-benzylidene-α-D-glucopyranoside (131614-84-1) + 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (572-09-8) → methyl 2-O-allyl-4,6-O-benzylidene-3-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-α-D-glucopyranoside (82185-93-1,131614-85-2)

Guidance literature:

With calcium sulfate; 4 A molecular sieve; mercury(II) cyanide; In nitromethane; benzene; at 35 ℃; for 72h;

DOI:10.1016/0008-6215(90)80103-A

Reference yield:

methyl-4,6-O-phenylmethylene-α-D-mannopyranoside (3162-96-7,4148-58-7,4153-17-7,4288-93-1,5328-47-2,6988-39-2,13566-32-0,14155-23-8,27994-50-9,37093-57-5,37093-59-7,57701-27-6,59168-66-0,64552-06-3,65391-13-1,65391-14-2,65530-26-9,66512-65-0,71117-36-7,71117-37-8,71117-41-4,72904-85-9,74560-56-8,79549-74-9,86783-81-5,96093-51-5,98633-13-7,110415-35-5,110415-36-6,110850-29-8,124020-29-7,126924-12-7,129263-21-4,131433-03-9,145920-49-6,146863-04-9) → methyl 2-O-allyl-4,6-O-benzylidene-3-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-α-D-mannopyranoside (82185-93-1,131614-85-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 76 percent / 50 percent sodium hydroxide / tetra-butylammonium hydrogen sulfate / CH₂Cl₂; H₂O / 20 h / Heating

2: 90 percent / mercuric bromide, mercuric cyanide, 4A molecular sieves / acetonitrile / 1 h / Ambient temperature

With sodium hydroxide; 4 A molecular sieve; mercury(II) cyanide; mercury dibromide; tetra(n-butyl)ammonium hydrogensulfate; In dichloromethane; water; acetonitrile;

DOI:10.1016/S0008-6215(82)80004-9

upstream raw materials:

methyl 2-O-allyl-4,6-O-benzylidene-α-D-glucopyranoside

2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide

4,6-O-benzylidene-1-O-methyl-α-D-glucopyranoside

methyl 2-O-allyl-4,6-O-benzylidene-α-D-mannopyranoside

Downstream raw materials:

methyl 2-O-allyl-3-O-(tetra-O-acetyl-α-D-mannopyranosyl)-α-D-mannopyranoside

methyl 3,6-di-O-(α-D-mannopyranosyl)-α-D-mannopyranoside

methyl 2-O-allyl-3,6-di-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-α-D-mannopyranoside