methyl 2-O-benzyl-4,6-O-benzylidene-3-O-p-methoxybenzyl-α-D-mannopyranoside

Base Information

• Chemical Name: methyl 2-O-benzyl-4,6-O-benzylidene-3-O-p-methoxybenzyl-α-D-mannopyranoside
• CAS No.: 216758-63-3
• Molecular Formula: C₂₉H₃₂O₇
• Molecular Weight: 492.569
• Mol file: 216758-63-3.mol

Synonyms:methyl 2-O-benzyl-4,6-O-benzylidene-3-O-p-methoxybenzyl-α-D-mannopyranoside

Chemical Property of methyl 2-O-benzyl-4,6-O-benzylidene-3-O-p-methoxybenzyl-α-D-mannopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 2-O-benzyl-4,6-O-benzylidene-3-O-p-methoxybenzyl-α-D-mannopyranoside

There total 3 articles about methyl 2-O-benzyl-4,6-O-benzylidene-3-O-p-methoxybenzyl-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: 79.0%

benzyl bromide (100-39-0) + methyl-4,6-O-benzylidene-3-O-(p-methoxybenzyl)-α-D-mannopyranoside (216758-62-2) → methyl 2-O-benzyl-4,6-O-benzylidene-3-O-p-methoxybenzyl-α-D-mannopyranoside (216758-63-3)

Guidance literature:

With tetra-(n-butyl)ammonium iodide; sodium hydride; In N,N-dimethyl-formamide; at 20 ℃; for 48h;

DOI:10.1080/07328309808001894

Reference yield:

p-methoxybenzyl chloride (824-94-2) → methyl 2-O-benzyl-4,6-O-benzylidene-3-O-p-methoxybenzyl-α-D-mannopyranoside (216758-63-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: dibutyltin oxide / toluene / 4 h / Heating

1.2: 68 percent / tetrabutylammonium iodide / toluene / 5 h / Heating

2.1: 79 percent / NaH; tetrabutylammonium iodide / dimethylformamide / 48 h / 20 °C

With tetra-(n-butyl)ammonium iodide; sodium hydride; di(n-butyl)tin oxide; In N,N-dimethyl-formamide; toluene; 1.1: Addition / 1.2: Alkylation / 2.1: Alkylation;

DOI:10.1080/07328309808001894

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-benzyl-4,6-O-benzylidene-3-O-p-methoxybenzyl-α-D-mannopyranoside (216758-63-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: dibutyltin oxide / toluene / 4 h / Heating

1.2: 68 percent / tetrabutylammonium iodide / toluene / 5 h / Heating

2.1: 79 percent / NaH; tetrabutylammonium iodide / dimethylformamide / 48 h / 20 °C

With tetra-(n-butyl)ammonium iodide; sodium hydride; di(n-butyl)tin oxide; In N,N-dimethyl-formamide; toluene; 1.1: Addition / 1.2: Alkylation / 2.1: Alkylation;

DOI:10.1080/07328309808001894

upstream raw materials:

benzyl bromide

methyl-4,6-O-benzylidene-3-O-(p-methoxybenzyl)-α-D-mannopyranoside

p-methoxybenzyl chloride

methyl-4,6-O-phenylmethylene-α-D-mannopyranoside

Downstream raw materials:

2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl-(1->3)-methyl-2-O-benzyl-4,6-O-benzylidene-α-D-mannopyranoside

methyl 2-O-benzyl-(R)-4,6-O-benzylidene-α-D-mannopyranoside