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

Base Information

• Chemical Name: 2-[(2R,4aR,6S,7R,8R,8aS)-8-Benzyloxy-6-(4-methoxy-phenoxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-5,6-dichloro-isoindole-1,3-dione
• CAS No.: 202864-94-6
• Molecular Formula: C₃₅H₂₉Cl₂NO₈
• Molecular Weight: 662.523

Synonyms:

Chemical Property of 2-[(2R,4aR,6S,7R,8R,8aS)-8-Benzyloxy-6-(4-methoxy-phenoxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-5,6-dichloro-isoindole-1,3-dione

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-[(2R,4aR,6S,7R,8R,8aS)-8-Benzyloxy-6-(4-methoxy-phenoxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-5,6-dichloro-isoindole-1,3-dione

There total 6 articles about 2-[(2R,4aR,6S,7R,8R,8aS)-8-Benzyloxy-6-(4-methoxy-phenoxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-5,6-dichloro-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:

benzyl bromide (100-39-0) + p-methoxyphenyl 4,6-O-benzylidene-2-deoxy-2-(4,5-dichlorophthalimido)-β-D-glucopyranoside (202864-93-5) → 2-[(2R,4aR,6S,7R,8R,8aS)-8-Benzyloxy-6-(4-methoxy-phenoxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-5,6-dichloro-isoindole-1,3-dione (202864-94-6)

Guidance literature:

With 4 A molecular sieve; sodium hydride; In N,N-dimethyl-formamide; at 6 ℃; for 28h;

DOI:10.1016/S0040-4020(97)10377-5

Reference yield:

4,5-dichlorophthalic anhydride (942-06-3) → 2-[(2R,4aR,6S,7R,8R,8aS)-8-Benzyloxy-6-(4-methoxy-phenoxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-5,6-dichloro-isoindole-1,3-dione (202864-94-6)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) Et₃N, 2.) Ac₂O, pyridine / 1) 1,2-dichloroethane, 50-60 deg C, 2 h; 2) rt, 24 h

2: 87 percent / TMSOTf / 1,2-dichloro-ethane / 42 h

3: 25 g / NaOMe / methanol; CH₂Cl₂ / 4 h / 0 °C

4: 74 percent / camphorsulphonic acid / dimethylformamide / 60 h / Ambient temperature

5: 4 Angstroem molecular sieves, NaH / dimethylformamide / 28 h / 6 °C

With pyridine; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; camphor-10-sulfonic acid; sodium methylate; acetic anhydride; sodium hydride; triethylamine; In methanol; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(97)10377-5

Reference yield:

1,3,4,6-tetra-O-acetyl-D-glucosamine hydrochloride (5432-46-2,10034-19-2,10034-20-5,34948-62-4,110253-00-4,1191127-63-5) → 2-[(2R,4aR,6S,7R,8R,8aS)-8-Benzyloxy-6-(4-methoxy-phenoxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-5,6-dichloro-isoindole-1,3-dione (202864-94-6)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) Et₃N, 2.) Ac₂O, pyridine / 1) 1,2-dichloroethane, 50-60 deg C, 2 h; 2) rt, 24 h

2: 87 percent / TMSOTf / 1,2-dichloro-ethane / 42 h

3: 25 g / NaOMe / methanol; CH₂Cl₂ / 4 h / 0 °C

4: 74 percent / camphorsulphonic acid / dimethylformamide / 60 h / Ambient temperature

5: 4 Angstroem molecular sieves, NaH / dimethylformamide / 28 h / 6 °C

With pyridine; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; camphor-10-sulfonic acid; sodium methylate; acetic anhydride; sodium hydride; triethylamine; In methanol; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(97)10377-5

upstream raw materials:

benzyl bromide

p-methoxyphenyl 4,6-O-benzylidene-2-deoxy-2-(4,5-dichlorophthalimido)-β-D-glucopyranoside

4,5-dichlorophthalic anhydride

1,3,4,6-tetra-O-acetyl-D-glucosamine hydrochloride

Downstream raw materials:

p-methoxyphenyl 3,6-di-O-benzyl-2-deoxy-2-(4,5-dichlorophthalimido)-β-D-glucopyranoside

4-Oxo-pentanoic acid (2R,3S,4R,5R,6R)-4-benzyloxy-2-benzyloxymethyl-5-(5,6-dichloro-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-hydroxy-tetrahydro-pyran-3-yl ester

4-Oxo-pentanoic acid (2R,3S,4R,5R,6S)-4-benzyloxy-2-benzyloxymethyl-5-(5,6-dichloro-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-(4-methoxy-phenoxy)-tetrahydro-pyran-3-yl ester

2-[(2S,3R,4R,5S,6R)-4-Benzyloxy-6-benzyloxymethyl-5-((2S,3R,4S,5R,6R)-6-benzyloxymethyl-3,4,5-trihydroxy-tetrahydro-pyran-2-yloxy)-2-(4-methoxy-phenoxy)-tetrahydro-pyran-3-yl]-5,6-dichloro-isoindole-1,3-dione

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