4-METHOXYPHENYL 3-O-BENZYL-4,6-O-BENZYLIDENE-2-DEOXY-2-PHTHALIMIDO-BETA-D-GLUCOPYRANOSIDE

Base Information

• Chemical Name: 4-METHOXYPHENYL 3-O-BENZYL-4,6-O-BENZYLIDENE-2-DEOXY-2-PHTHALIMIDO-BETA-D-GLUCOPYRANOSIDE
• CAS No.: 129575-88-8
• Molecular Formula: C35H31 N O8
• Molecular Weight: 593.633
• Hs Code.: 29389090
• Mol file: 129575-88-8.mol

Synonyms:b-D-Glucopyranoside, 4-methoxyphenyl2-deoxy-2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-3-O-(phenylmethyl)-4,6-O-(phenylmethylene)-,(R)-; Pyrano[3,2-d]-1,3-dioxin, b-D-glucopyranoside deriv.

Chemical Property of 4-METHOXYPHENYL 3-O-BENZYL-4,6-O-BENZYLIDENE-2-DEOXY-2-PHTHALIMIDO-BETA-D-GLUCOPYRANOSIDE

Chemical Property:

• Melting Point: 133 °C
• Refractive Index: 92 ° (C=1, CHCl3)
• PSA: 92.76000
• LogP: 5.10120
• Storage Temp.: Freezer
• Solubility.: almost transparency in Chloroform

Purity/Quality:

98%,99%, ^*data from raw suppliers

4-Methoxyphenyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-b-D-glucopyranoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 4-METHOXYPHENYL 3-O-BENZYL-4,6-O-BENZYLIDENE-2-DEOXY-2-PHTHALIMIDO-BETA-D-GLUCOPYRANOSIDE

There total 10 articles about 4-METHOXYPHENYL 3-O-BENZYL-4,6-O-BENZYLIDENE-2-DEOXY-2-PHTHALIMIDO-BETA-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: 83.0%

4-methoxyphenyl 4,6-di-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranoside (138906-43-1) + benzyl bromide (100-39-0) → p-Methoxyphenyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranoside (129575-88-8)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; at 0 ℃; for 1h;

DOI:10.1039/c8ob01046c

Reference yield:

4-methoxylphenzyl 2-deoxy-2-phthalimido-3,4,6-tri-O-acetyl-β-D-glucopyranoside (138906-41-9) → p-Methoxyphenyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranoside (129575-88-8)

Guidance literature:

Multi-step reaction with 2 steps

1: p-TsOH*H₂O / dimethylformamide / 20 h / 20 °C

2: 61 percent / NaH / dimethylformamide / 20 h / 20 °C

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

DOI:10.1016/0008-6215(93)84080-P

Reference yield:

p-Methoxyphenyl 2-deoxy-2-phthalimido-β-D-glucopyranoside (138906-42-0) → p-Methoxyphenyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranoside (129575-88-8)

Guidance literature:

Multi-step reaction with 2 steps

1: TsOH*H₂O / dimethylformamide

2: NaH / dimethylformamide

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

DOI:10.1016/0040-4039(90)80026-I

upstream raw materials:

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

benzyl bromide

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

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

Downstream raw materials:

p-methoxyphenyl 3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

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

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

p-Methoxyphenyl O-(2,4-di-O-acetyl-3,6-di-O-allyl-β-D-galactopyranosyl)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

Refernces

• 1、 -. "NOVEL INTERMEDIATES FOR THE PREPARATION OF GBS POLYSACCHARIDE ANTIGENS". Paragraph 0066; 0071-0074. . Retrieved 2019/01/30.
• 2、 Li, Wei,Gao, Yu,Li, Qing,Li, Zhong-Jun. "Ionic-liquid supported rapid synthesis of an: N -glycan core pentasaccharide on a 10 g scale". supporting information. p. 4720 - 4727. Retrieved 2018/07/06.