methyl 4,6-O-benzylidene-2-deoxy-2-dimethylmaleimido-β-D-glucopyranoside

Base Information

• Chemical Name: methyl 4,6-O-benzylidene-2-deoxy-2-dimethylmaleimido-β-D-glucopyranoside
• CAS No.: 678159-26-7
• Molecular Formula: C₂₀H₂₃NO₇
• Molecular Weight: 389.405

Synonyms:methyl 4,6-O-benzylidene-2-deoxy-2-dimethylmaleimido-β-D-glucopyranoside

Chemical Property of methyl 4,6-O-benzylidene-2-deoxy-2-dimethylmaleimido-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

98% ^*data from raw suppliers

Safty Information:

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Technology Process of methyl 4,6-O-benzylidene-2-deoxy-2-dimethylmaleimido-β-D-glucopyranoside

There total 2 articles about methyl 4,6-O-benzylidene-2-deoxy-2-dimethylmaleimido-β-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: 85.0%

benzaldehyde dimethyl acetal (1125-88-8) + 1-((2R,3R,4R,5S,6R)-4,5-Dihydroxy-6-hydroxymethyl-2-methoxy-tetrahydro-pyran-3-yl)-3,4-dimethyl-pyrrole-2,5-dione (898547-26-7) → methyl 4,6-O-benzylidene-2-deoxy-2-dimethylmaleimido-β-D-glucopyranoside (678159-26-7)

Guidance literature:

With camphor-10-sulfonic acid; In N,N-dimethyl-formamide; at 20 ℃;

DOI:10.1016/j.carres.2006.03.030

Reference yield:

methyl 3,4,6-tri-O-acetyl-2-deoxy-2-dimethylmaleimido-β-D-glucopyranoside (676487-75-5) → methyl 4,6-O-benzylidene-2-deoxy-2-dimethylmaleimido-β-D-glucopyranoside (678159-26-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 100 percent / NaOMe / methanol / 2.5 h / 20 °C

2: 85 percent / camphorsulfonic acid / dimethylformamide / 20 °C

With camphor-10-sulfonic acid; sodium methylate; In methanol; N,N-dimethyl-formamide;

DOI:10.1016/j.carres.2006.03.030

Reference yield: 99.0%

methyl 4,6-O-benzylidene-2-deoxy-2-dimethylmaleimido-β-D-glucopyranoside (678159-26-7) + O-benzyl 2,2,2-trichloroacetimidate (81927-55-1) → 1-((2R,4aR,6R,7R,8R,8aS)-8-Benzyloxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-3,4-dimethyl-pyrrole-2,5-dione (898547-28-9)

Guidance literature:

With trifluorormethanesulfonic acid; In dichloromethane; for 2.5h; cooling;

DOI:10.1016/j.carres.2006.03.030

upstream raw materials:

benzaldehyde dimethyl acetal

1-((2R,3R,4R,5S,6R)-4,5-Dihydroxy-6-hydroxymethyl-2-methoxy-tetrahydro-pyran-3-yl)-3,4-dimethyl-pyrrole-2,5-dione

methyl 3,4,6-tri-O-acetyl-2-deoxy-2-dimethylmaleimido-β-D-glucopyranoside

Downstream raw materials:

1-((2R,4aR,6R,7R,8R,8aS)-8-Benzyloxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-3,4-dimethyl-pyrrole-2,5-dione

Benzoic acid (2R,4aR,6R,7R,8R,8aS)-7-(3,4-dimethyl-2,5-dioxo-2,5-dihydro-pyrrol-1-yl)-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester

1-((2R,3R,4R,5S,6R)-4-Benzyloxy-6-benzyloxymethyl-5-hydroxy-2-methoxy-tetrahydro-pyran-3-yl)-3,4-dimethyl-pyrrole-2,5-dione

Benzoic acid (2R,3S,4R,5R,6R)-2-benzyloxymethyl-5-(3,4-dimethyl-2,5-dioxo-2,5-dihydro-pyrrol-1-yl)-3-hydroxy-6-methoxy-tetrahydro-pyran-4-yl ester

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