methyl 2-acetamido-4,6-O-benzylidene-3-O-(3,4-O-benzylidene-α-L-arabinopyranosyl)-2-deoxy-β-D-glucopyranoside

Base Information

• Chemical Name: methyl 2-acetamido-4,6-O-benzylidene-3-O-(3,4-O-benzylidene-α-L-arabinopyranosyl)-2-deoxy-β-D-glucopyranoside
• CAS No.: 144684-98-0
• Molecular Formula: C₂₈H₃₃NO₁₀
• Molecular Weight: 543.571

Synonyms:methyl 2-acetamido-4,6-O-benzylidene-3-O-(3,4-O-benzylidene-α-L-arabinopyranosyl)-2-deoxy-β-D-glucopyranoside

Chemical Property of methyl 2-acetamido-4,6-O-benzylidene-3-O-(3,4-O-benzylidene-α-L-arabinopyranosyl)-2-deoxy-β-D-glucopyranoside

Chemical Property:

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Technology Process of methyl 2-acetamido-4,6-O-benzylidene-3-O-(3,4-O-benzylidene-α-L-arabinopyranosyl)-2-deoxy-β-D-glucopyranoside

There total 2 articles about methyl 2-acetamido-4,6-O-benzylidene-3-O-(3,4-O-benzylidene-α-L-arabinopyranosyl)-2-deoxy-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:

methyl 2-acetamido-4,6-O-benzylidene-2-deoxy-3-O-(2,3,4-tri-O-acetyl-α-L-araninopyranosyl)-α-D-glucopyranoside (118344-52-8) → methyl 2-acetamido-4,6-O-benzylidene-3-O-(3,4-O-benzylidene-α-L-arabinopyranosyl)-2-deoxy-β-D-glucopyranoside (144684-98-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 0.05 N methanolic MeONa / CH₂Cl₂ / 5 h / Ambient temperature

2: p-toluenesulfonic acid / dimethylformamide; acetonitrile / 24 h

With sodium methylate; toluene-4-sulfonic acid; In dichloromethane; N,N-dimethyl-formamide; acetonitrile;

Reference yield:

benzaldehyde dimethyl acetal (1125-88-8) + N-[(2R,4aR,6R,7R,8R,8aS)-6-Methoxy-2-phenyl-8-((2S,3R,4S,5S)-3,4,5-trihydroxy-tetrahydro-pyran-2-yloxy)-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-acetamide → methyl 2-acetamido-4,6-O-benzylidene-3-O-(3,4-O-benzylidene-α-L-arabinopyranosyl)-2-deoxy-β-D-glucopyranoside (144684-98-0)

Guidance literature:

toluene-4-sulfonic acid; In N,N-dimethyl-formamide; acetonitrile; for 24h; Yield given;

Reference yield: 81.0%

perbenzyl fucosyl bromide (33639-77-9) + methyl 2-acetamido-4,6-O-benzylidene-3-O-(3,4-O-benzylidene-α-L-arabinopyranosyl)-2-deoxy-β-D-glucopyranoside (144684-98-0) → methyl 2-acetamido-4,6-O-benzylidene-3-O-<3,4-O-benzylidene-2-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-α-L-arabinopyranosyl>-2-deoxy-β-D-glucopyranoside (144684-99-1)

Guidance literature:

With 4 A molecular sieve; tetraethylammonium bromide; In dichloromethane; N,N-dimethyl-formamide; for 30h;

upstream raw materials:

benzaldehyde dimethyl acetal

methyl 2-acetamido-4,6-O-benzylidene-2-deoxy-3-O-(2,3,4-tri-O-acetyl-α-L-araninopyranosyl)-α-D-glucopyranoside

Downstream raw materials:

methyl 2-acetamido-4,6-O-benzylidene-3-O-<3,4-O-benzylidene-2-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-α-L-arabinopyranosyl>-2-deoxy-β-D-glucopyranoside

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