2-[(4aR,6R,7R,8R,8aS)-6-Allyloxy-8-hydroxy-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-isoindole-1,3-dione

Base Information

• Chemical Name: 2-[(4aR,6R,7R,8R,8aS)-6-Allyloxy-8-hydroxy-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-isoindole-1,3-dione
• CAS No.: 165553-70-8
• Molecular Formula: C₂₅H₂₅NO₈
• Molecular Weight: 467.475
• Mol file: 165553-70-8.mol

Synonyms:2-[(4aR,6R,7R,8R,8aS)-6-Allyloxy-8-hydroxy-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-isoindole-1,3-dione

Chemical Property of 2-[(4aR,6R,7R,8R,8aS)-6-Allyloxy-8-hydroxy-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-isoindole-1,3-dione

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-[(4aR,6R,7R,8R,8aS)-6-Allyloxy-8-hydroxy-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-isoindole-1,3-dione

There total 2 articles about 2-[(4aR,6R,7R,8R,8aS)-6-Allyloxy-8-hydroxy-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-isoindole-1,3-dione 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: 88.0%

p-Anisaldehyde dimethyl acetal (2186-92-7) + allyl 2-deoxy-2-phthalimido-β-D-glucopyranoside (114853-29-1) → 2-[(4aR,6R,7R,8R,8aS)-6-Allyloxy-8-hydroxy-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-isoindole-1,3-dione (165553-70-8)

Guidance literature:

With camphor-10-sulfonic acid; In toluene; at 90 ℃; for 20h;

DOI:10.1021/jo0485841

Reference yield:

allyl 3,4,6-tri-O-acetyl-2-deoxy-2-N-phthalimido-β-D-glucopyranoside (72333-26-7) → 2-[(4aR,6R,7R,8R,8aS)-6-Allyloxy-8-hydroxy-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-isoindole-1,3-dione (165553-70-8)

Guidance literature:

Multi-step reaction with 2 steps

1: NaOMe / CH₂Cl₂; methanol / 2 h / 0 °C

2: 88 percent / camphorsulfonic acid / toluene / 20 h / 90 °C

With camphor-10-sulfonic acid; sodium methylate; In methanol; dichloromethane; toluene;

DOI:10.1021/jo0485841

Reference yield: 68.0%

acetic anhydride (108-24-7) + 2-[(4aR,6R,7R,8R,8aS)-6-Allyloxy-8-hydroxy-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-isoindole-1,3-dione (165553-70-8) → allyl 3-O-acetyl-2-deoxy-4,6-O-(p-methoxybenzylidene)-2-phthalimido-β-D-glucopyranoside (791790-10-8)

Guidance literature:

With pyridine; at 20 ℃; for 24h;

DOI:10.1021/jo0485841

upstream raw materials:

p-Anisaldehyde dimethyl acetal

allyl 2-deoxy-2-phthalimido-β-D-glucopyranoside

allyl 3,4,6-tri-O-acetyl-2-deoxy-2-N-phthalimido-β-D-glucopyranoside

Downstream raw materials:

allyl 3-O-acetyl-2-deoxy-4,6-O-(p-methoxybenzylidene)-2-phthalimido-β-D-glucopyranoside

allyl (6S)-3-O-acetyl-2-deoxy-6-O-(p-methoxybenzyl)-6-C-methyl-2-phthalimido-β-D-glucopyranoside

allyl (6R)-3-O-acetyl-2-deoxy-6-O-(p-methoxybenzyl)-6-C-methyl-2-phthalimido-β-D-glucopyranoside

allyl (6S)-3-O-acetyl-2-deoxy-4-O-(2-deoxy-2-phthalimido-3,4,6-tri-O-acetyl-β-D-glucopyranosyl)-6-O-(p-methoxybenzyl)-6-C-methyl-2-phthalimido-β-D-glucopyranoside