4-methoxyphenyl 3-O-allyloxycarbonyl-2-deoxy-4,6-O-isopropylidene-2-phthalimido-β-D-glucopyranoside

Base Information

• Chemical Name: 4-methoxyphenyl 3-O-allyloxycarbonyl-2-deoxy-4,6-O-isopropylidene-2-phthalimido-β-D-glucopyranoside
• CAS No.: 144367-36-2
• Molecular Formula: C₂₈H₂₉NO₁₀
• Molecular Weight: 539.539

Synonyms:4-methoxyphenyl 3-O-allyloxycarbonyl-2-deoxy-4,6-O-isopropylidene-2-phthalimido-β-D-glucopyranoside

Chemical Property of 4-methoxyphenyl 3-O-allyloxycarbonyl-2-deoxy-4,6-O-isopropylidene-2-phthalimido-β-D-glucopyranoside

Chemical Property:

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Technology Process of 4-methoxyphenyl 3-O-allyloxycarbonyl-2-deoxy-4,6-O-isopropylidene-2-phthalimido-β-D-glucopyranoside

There total 2 articles about 4-methoxyphenyl 3-O-allyloxycarbonyl-2-deoxy-4,6-O-isopropylidene-2-phthalimido-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: 96.0%

4-methoxyphenyl 2-deoxy-4,6-O-isopropylidene-2-phthalimido-β-D-glucopyranoside (144367-30-6) + Allyl chloroformate (2937-50-0) → 4-methoxyphenyl 3-O-allyloxycarbonyl-2-deoxy-4,6-O-isopropylidene-2-phthalimido-β-D-glucopyranoside (144367-36-2)

Guidance literature:

With pyridine; In dichloromethane; at -35 ℃;

DOI:10.1016/S0008-6215(00)90971-6

Reference yield:

p-Methoxyphenyl 2-deoxy-2-phthalimido-β-D-glucopyranoside (138906-42-0) → 4-methoxyphenyl 3-O-allyloxycarbonyl-2-deoxy-4,6-O-isopropylidene-2-phthalimido-β-D-glucopyranoside (144367-36-2)

Guidance literature:

Multi-step reaction with 2 steps

1: p-TsOH / dimethylformamide / 86 h

2: 96 percent / pyridine / CH₂Cl₂ / -35 °C

With pyridine; toluene-4-sulfonic acid; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0008-6215(00)90971-6

Reference yield:

4-methoxyphenyl 3-O-allyloxycarbonyl-2-deoxy-4,6-O-isopropylidene-2-phthalimido-β-D-glucopyranoside (144367-36-2) → Carbonic acid allyl ester (2S,3R,4R,5S,6R)-3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-5-hydroxy-6-hydroxymethyl-2-(4-methoxy-phenoxy)-tetrahydro-pyran-4-yl ester

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 4h;

DOI:10.1002/ejoc.200400255

upstream raw materials:

4-methoxyphenyl 2-deoxy-4,6-O-isopropylidene-2-phthalimido-β-D-glucopyranoside

Allyl chloroformate

p-Methoxyphenyl 2-deoxy-2-phthalimido-β-D-glucopyranoside

Downstream raw materials:

4-methoxyphenyl 4,6-di-O-acetyl-3-O-allyloxycarbonyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

allyl (4,6-di-O-acetyl-3-O-allyloxycarbonyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->3)-2,4-di-O-acetyl-6-O-(tert-butyldiphenylsilyl)-α-L-galactopyranoside

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