methyl 2-O-benzyl-4,6-O-benzylidene-3-O-(4-methoxybenzyl)-α-D-glucopyranoside

Base Information

• Chemical Name: methyl 2-O-benzyl-4,6-O-benzylidene-3-O-(4-methoxybenzyl)-α-D-glucopyranoside
• CAS No.: 202648-53-1
• Molecular Formula: C₂₉H₃₂O₇
• Molecular Weight: 492.569

Synonyms:methyl 2-O-benzyl-4,6-O-benzylidene-3-O-(4-methoxybenzyl)-α-D-glucopyranoside

Chemical Property of methyl 2-O-benzyl-4,6-O-benzylidene-3-O-(4-methoxybenzyl)-α-D-glucopyranoside

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-(4-methoxybenzyl)-α-D-glucopyranoside

There total 5 articles about methyl 2-O-benzyl-4,6-O-benzylidene-3-O-(4-methoxybenzyl)-α-D-glucopyranoside 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: 91.0%

O-(4-methoxybenzyl)-trichloroacetimidate (89238-99-3) + methyl 2-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside (76375-66-1) → methyl 2-O-benzyl-4,6-O-benzylidene-3-O-(4-methoxybenzyl)-α-D-glucopyranoside (202648-53-1)

Guidance literature:

lanthanum(lll) triflate; In toluene; at 20 ℃; for 0.0833333h;

DOI:10.1016/S0040-4039(03)00282-X

Reference yield: 71.0%

methyl 2,3,4,6-tetrakis-O-trimethylsilyl-α-D-glucopyranoside (2641-79-4) + benzyl bromide (100-39-0) + 4-chlorobenzaldehyde (104-88-1) + benzaldehyde (100-52-7) + 4-methoxy-benzaldehyde (123-11-5) + 1-Chloro-4-(chloromethyl)benzene (104-83-6) + 4-bromo-benzaldehyde (1122-91-4) + β-naphthaldehyde (66-99-9) + allyl bromide (106-95-6) + 1-bromomethyl-4-bromobenzene (589-15-1) + p-methoxybenzyl chloride (824-94-2) + 2-bromomethylnaphthyl bromide (939-26-4) → C25H30O7 (942043-65-4) + C24H27ClO6 (942043-76-7) + C24H27BrO6 (942043-81-4) + C28H29ClO6 (942043-58-5) + C28H29BrO6 (942043-59-6) + C28H29BrO6 (942043-79-0) + C28H29ClO6 (942043-73-4) + C28H30O6 (942043-71-2) + C28H30O6 (942043-87-0) + C32H32O6 (942043-57-4) + C32H32O6 (942043-68-7) + C29H31BrO7 (942043-64-3) + C28H28BrClO6 (942043-75-6) + C29H31ClO7 (942043-63-2) + C32H31ClO6 (942043-86-9) + C33H34O7 (942043-84-7) + methyl 4,6-O-benzylidene-2-O-(p-methoxybenzyl)-3-O-(2-naphthyl)methyl-α-D-glucopyranoside (942043-69-8) + methyl 4,6-O-benzylidene-3-O-(p-methoxybenzyl)-2-O-(2-naphthyl)methyl-α-D-glucopyranoside (942043-62-1) + C32H31BrO6 (942043-80-3) + C32H31BrO6 (942043-70-1) + C32H31ClO6 (942043-74-5) + C36H34O6 (942043-85-8) + methyl 2-O-allyl-3-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside (157903-83-8) + methyl 2,3-di-O-benzyl-4,6-O-(2-naphthyl)methylene-α-D-glucopyranoside (291314-22-2) + methyl 2-O-benzyl-4,6-O-benzylidene-3-O-(4-methoxybenzyl)-α-D-glucopyranoside (202648-53-1)

Guidance literature:

methyl 2,3,4,6-tetrakis-O-trimethylsilyl-α-D-glucopyranoside; benzaldehyde; β-naphthaldehyde; trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -86 ℃; for 2h; Molecular sieve; Combinatorial reaction / High throughput screening (HTS);

4-chlorobenzaldehyde; benzaldehyde; 4-methoxy-benzaldehyde; 4-bromo-benzaldehyde; β-naphthaldehyde; With triethylsilane; trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -86 ℃; for 5h; Combinatorial reaction / High throughput screening (HTS);

benzyl bromide; 1-Chloro-4-(chloromethyl)benzene; allyl bromide; 1-bromomethyl-4-bromobenzene; p-methoxybenzyl chloride; 2-bromomethylnaphthyl bromide; With tetrabutyl ammonium fluoride; sodium hydride; more than 3 stages;

Reference yield:

benzyl bromide (100-39-0) → methyl 2-O-benzyl-4,6-O-benzylidene-3-O-(4-methoxybenzyl)-α-D-glucopyranoside (202648-53-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: Bu₂SnO / benzene / 12 h / Heating

1.2: 76 percent / heptane / 72 h / Heating

2.1: NaH / dimethylformamide; various solvent(s) / 2 h

With sodium hydride; di(n-butyl)tin oxide; In N,N-dimethyl-formamide; benzene;

DOI:10.1071/CH03203

upstream raw materials:

O-(4-methoxybenzyl)-trichloroacetimidate

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

p-methoxybenzyl chloride

benzyl bromide

Downstream raw materials:

methyl 2-O-benzyl-3-O-(4-methoxybenzyl)-α-D-glucopyranoside

(3R,4S,5R,6S)-3-acetoxy-4,6-di(benzyloxy)-3-benzyloxymethyl-5-[(4-methoxybenzyl)oxy]cyclohexene

(3R,4S,5S,6R)-3-azido-4,6-di(benzyloxy)-1-benzyloxymethyl-5-[(4-methoxybenzyl)oxy]cyclohexene

(1R,4S,5R,6S)-4,6-di(benzyloxy)-1-benzyloxymethyl-5-[(4-methoxybenzyl)oxy]cyclohex-2-en-1-ol

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