.beta.-D-Glucopyranoside, 2-propenyl 2-deoxy-2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-4,6-O-(phenylmethylene)-

Base Information

• Chemical Name: .beta.-D-Glucopyranoside, 2-propenyl 2-deoxy-2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-4,6-O-(phenylmethylene)-
• CAS No.: 114853-35-9
• Molecular Formula: C24H23 N O7
• Molecular Weight: 437.449
• Mol file: 114853-35-9.mol

Synonyms:b-D-Glucopyranoside, 2-propenyl2-deoxy-2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-4,6-O-(phenylmethylene)-(9CI); Pyrano[3,2-d]-1,3-dioxin, b-D-glucopyranoside deriv.

Chemical Property of .beta.-D-Glucopyranoside, 2-propenyl 2-deoxy-2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-4,6-O-(phenylmethylene)-

Chemical Property:

• PSA: 94.53000
• LogP: 1.99170

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of .beta.-D-Glucopyranoside, 2-propenyl 2-deoxy-2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-4,6-O-(phenylmethylene)-

There total 6 articles about .beta.-D-Glucopyranoside, 2-propenyl 2-deoxy-2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-4,6-O-(phenylmethylene)- 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: 95.0%

benzaldehyde dimethyl acetal (1125-88-8) + allyl 2-deoxy-2-phthalimido-β-D-glucopyranoside (114853-29-1) → allyl 4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranoside (114853-35-9)

Guidance literature:

With toluene-4-sulfonic acid; In N,N-dimethyl-formamide; at 50 ℃;

Reference yield: 82.0%

Benzaldehyde dipent-4-enyl acetal (2031-48-3) + allyl 2-deoxy-2-phthalimido-β-D-glucopyranoside (114853-29-1) → allyl 4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranoside (114853-35-9)

Guidance literature:

With N-Bromosuccinimide; triethylsilyl trifluoromethyl sulfonate; In acetonitrile; for 0.0833333h; Ambient temperature;

DOI:10.1021/jo00108a056

Reference yield:

benzaldehyde (100-52-7) → allyl 4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranoside (114853-35-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 76 percent / p-TsOH, molecular sieves 4 Angstroem / hexane / 8 h / 0 °C

2: 82 percent / NBS, Et₃SiOTf / acetonitrile / 0.08 h / Ambient temperature

With N-Bromosuccinimide; 4 A molecular sieve; triethylsilyl trifluoromethyl sulfonate; toluene-4-sulfonic acid; In hexane; acetonitrile;

DOI:10.1021/jo00108a056

upstream raw materials:

benzaldehyde dimethyl acetal

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

benzaldehyde

Benzaldehyde dipent-4-enyl acetal

Downstream raw materials:

O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1-> 3)-[O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1-> 4)]-6-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranose

Acetic acid (2R,3R,4R,5S,6R)-2-allyloxy-6-benzyloxymethyl-3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-5-((2S,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yl ester

allyl O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1-4)-O-<(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1-3)>-6-O-benzyl-2-deoxy-2-phtalimido-β-D-glucopyranoside

allyl O-(2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)-(1-3)-6-O-benzyl-2-deoxy-2-phtalimido-β-D-glucopyranoside

Refernces

• 1、 Madsen, Robert,Fraser-Reid, Bert. "Acetal Transfer via Halonium-Ion Induced Reactions of Dipent-4-enyl Acetals: Scope and Mechanism". . p. 772 - 779. Retrieved 2007/10/02.
• 2、 El-Sokkary, Ramadan I.,Silwanis, Basim Azmy,Nashed, Mina A.,Paulsen, Hans. ""Standardized intermediates" for oligosaccharide synthesis: convenient preparation of 2-amino-2-deoxy-D-glucose derivatives and their conversion into the D-galactose analogues". . p. 319 - 323. Retrieved 2007/10/02.