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

Base Information

• Chemical Name: benzyl 4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranoside
• CAS No.: 149342-15-4
• Molecular Formula: C₂₈H₂₅NO₇
• Molecular Weight: 487.509
• Mol file: 149342-15-4.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 5 articles about benzyl 4,6-O-benzylidene-2-deoxy-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: 93.0%

benzaldehyde dimethyl acetal (1125-88-8) + benzyl 2-deoxy-2-phthalimido-β-D-glucopyranoside (80035-32-1) → benzyl 4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranoside (149342-15-4)

Guidance literature:

With toluene-4-sulfonic acid; In acetonitrile; for 15h; Heating;

DOI:10.1021/jo962362o

Reference yield:

1,3,4,6-tetra-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranose (10022-13-6) → benzyl 4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranoside (149342-15-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 93 percent / conc. HCl / acetone; H₂O / 16 h / 80 °C

2: 93 percent / p-toluenesulfonic acid / acetonitrile / 15 h / Heating

With hydrogenchloride; toluene-4-sulfonic acid; In water; acetone; acetonitrile;

DOI:10.1021/jo962362o

Reference yield:

benzyl 2-phthalimido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside (80035-31-0) → benzyl 4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranoside (149342-15-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 97 percent / conc. hydrochloric acid / H₂O; acetone / 6 h / 70 °C

2: 92 percent / p-toluenesulfonic acid / acetonitrile / 16 h / Ambient temperature

With hydrogenchloride; toluene-4-sulfonic acid; In water; acetone; acetonitrile;

DOI:10.1139/v82-010

upstream raw materials:

benzaldehyde dimethyl acetal

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

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

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

Downstream raw materials:

benzyl 3-O-(tetra-O-acetyl-β-D-galactopyranosyl)-4,6-O-benzylidine-2-deoxy-2-phthalimido-β-D-glucopyranoside

3,4,5,7-tetra-O-acetyl-2,6-anhydro-D-glycero-L-manno-heptonitrile

benzyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranoside

benzyl 4,6-O-benzylidene-2-deoxy-3-O-p-methoxybenzyl-2-phthalimido-β-D-glucopyranoside