Benzyl 2-Deoxy-2-phthalimido-4,6-O-benzylidene-3-O-benzyl--D-glucopyranoside

Base Information

• Chemical Name: Benzyl 2-Deoxy-2-phthalimido-4,6-O-benzylidene-3-O-benzyl--D-glucopyranoside
• CAS No.: 80035-34-3
• Molecular Formula: C35H31NO7
• Molecular Weight: 577.634
• Mol file: 80035-34-3.mol

Synonyms:Benzyl 2-Deoxy-2-phthalimido-4,6-O-benzylidene-3-O-benzyl-|A-D-glucopyranoside;

Chemical Property of Benzyl 2-Deoxy-2-phthalimido-4,6-O-benzylidene-3-O-benzyl--D-glucopyranoside

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 716.289°C at 760 mmHg
• Flash Point: 386.998°C
• PSA: 83.53000
• Density: 1.364g/cm³
• LogP: 5.23040
• Solubility.: Chloroform, Dichloromethane, Ethyl Acetate, Methanol

Purity/Quality:

97% ^*data from raw suppliers

Benzyl2-Deoxy-2-phthalimido-4,6-O-benzylidene-3-O-benzyl-β-D-glucopyranoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Benzyl 2-Deoxy-2-phthalimido-4,6-O-benzylidene-3-O-benzyl--D-glucopyranoside

There total 9 articles about Benzyl 2-Deoxy-2-phthalimido-4,6-O-benzylidene-3-O-benzyl--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: 82.0%

Ethyl 4,6-O-benzylidene-3-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside + benzyl alcohol (100-51-6,185532-71-2) → 2-((4aR,6R,7R,8R,8aS)-6,8-Bis-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-isoindole-1,3-dione (80035-34-3)

Guidance literature:

With N-iodo-succinimide; trifluorormethanesulfonic acid; 3 A molecular sieve; In acetonitrile; at -40 ℃;

DOI:10.1002/(SICI)1521-3773(20000204)39:3<531::AID-ANIE531>3.0.CO;2-F

Reference yield: 81.0%

tetrabutylammonium 1,3-dioxoisoindolin-2-ide (85151-15-1) + benzyl 3-O-benzyl-4,6-O-benzylidene-2-O-trifluoromethanesulfonyl-α-D-mannopyranoside (121237-32-9) → benzyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-α-D-erythro-hex-2-enopyranoside (121237-34-1) + 2-((4aR,6S,7R,8R,8aS)-6,8-Bis-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-isoindole-1,3-dione (80035-34-3,121312-40-1)

Guidance literature:

In toluene; at 50 ℃; for 48h;

DOI:10.1016/0008-6215(89)84013-3

Reference yield:

1,3,4,6-tetra-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranose (10022-13-6) → 2-((4aR,6R,7R,8R,8aS)-6,8-Bis-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-isoindole-1,3-dione (80035-34-3)

Guidance literature:

Multi-step reaction with 4 steps

2: 92 percent / conc. HCl / acetone / 70 °C

3: 82 percent / TsOH / dimethylformamide / 50 °C

4: 1.) NaH / 1.) DMF, room temperature, 30 min, 2.) room temperature, 5 h

With hydrogenchloride; sodium hydride; toluene-4-sulfonic acid; In N,N-dimethyl-formamide; acetone;

upstream raw materials:

benzyl bromide

benzyl 4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranoside

benzyl alcohol

1,3,4,6-tetra-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranose

Downstream raw materials:

benzyl 3-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

2-[(2R,3R,4R,5S,6R)-2,4-Bis-benzyloxy-5-hydroxy-6-(4-methoxy-phenoxymethyl)-tetrahydro-pyran-3-yl]-isoindole-1,3-dione

C₆₃H₅₈N₂O₁₄

acetic acid 4-benzyloxy-2-benzyloxymethyl-6-[4,6-bis-benzyloxy-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2-(4-methoxy-phenoxymethyl)-tetrahydro-pyran-3-yloxy]-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-tetrahydro-pyran-3-yl ester