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

Base Information

• Chemical Name: Benzyl 2-Deoxy-2-phthalimido-4,6-O-benzylidene--D-glucopyranoside
• CAS No.: 80035-33-2
• Molecular Formula: C28H25NO7
• Molecular Weight: 487.509
• Hs Code.: 2938909090
• Mol file: 80035-33-2.mol

Synonyms:Benzyl 2-Deoxy-2-phthalimido-4,6-O-benzylidene--D-glucopyranoside;PhenylMethyl 2-Deoxy-2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-4,6-O-(phenylMethylene)-β-D-glucopyranoside;Phenylmethyl 2-deoxy-2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-4,6-O-(phenylmethylene)-beta-D-glucopyranoside

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

Chemical Property:

• Melting Point: 180-182°C
• Boiling Point: 685.1±55.0 °C(Predicted)
• PKA: 12.68±0.70(Predicted)
• PSA: 94.53000
• Density: 1.43±0.1 g/cm3 (20 oC 760 Torr)
• LogP: 3.00590
• Solubility.: Chloroform, Dichloromethane, Methanol

Purity/Quality:

98% ^*data from raw suppliers

Benzyl2-Deoxy-2-phthalimido-4,6-O-benzylidene-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--D-glucopyranoside

There total 8 articles about Benzyl 2-Deoxy-2-phthalimido-4,6-O-benzylidene--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%

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 (80035-33-2)

Guidance literature:

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

Reference yield: 60.0%

benzyl 2-deoxy-2-phthalimido-β-D-glucopyranoside (80035-32-1) + benzaldehyde (100-52-7) → benzyl 4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranoside (80035-33-2)

Guidance literature:

With zinc(II) chloride; for 23h; Ambient temperature;

DOI:10.1016/S0040-4039(97)00729-6

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 (80035-33-2)

Guidance literature:

Multi-step reaction with 3 steps

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

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

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

upstream raw materials:

benzaldehyde dimethyl acetal

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

benzaldehyde

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

Downstream raw materials:

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

Succinic acid (2R,3R,4R,5S,6R)-2-benzyloxy-6-benzyloxymethyl-3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-5-hydroxy-tetrahydro-pyran-4-yl ester (2S,3R,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-phenylsulfanyl-tetrahydro-pyran-3-yl ester

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

benzyl 3-O-benzyl-2-deoxy-2-phthalimido-6-O-pivaloyl-β-D-glucopyranoside