4-METHOXYPHENYL 2,6-DI-O-BENZYL-3,4-O-ISOPROPYLIDENE-BETA-D-GALACTOPYRANOSIDE

Base Information

• Chemical Name: 4-METHOXYPHENYL 2,6-DI-O-BENZYL-3,4-O-ISOPROPYLIDENE-BETA-D-GALACTOPYRANOSIDE
• CAS No.: 159922-68-6
• Molecular Formula: C30H34 O7
• Molecular Weight: 506.596
• Hs Code.: 29389090
• Mol file: 159922-68-6.mol

Synonyms:4-METHOXYPHENYL 2,6-DI-O-BENZYL-3,4-O-ISOPROPYLIDENE-BETA-D-GALACTOPYRANOSIDE;4-Methoxyphenyl2,6-di-O-benzyl-3,4-O-isopropylidene-b-D-galactopyranose

Chemical Property of 4-METHOXYPHENYL 2,6-DI-O-BENZYL-3,4-O-ISOPROPYLIDENE-BETA-D-GALACTOPYRANOSIDE

Chemical Property:

• Melting Point: 102.0 to 107.0 °C
• Refractive Index: 1.593
• PSA: 64.61000
• LogP: 5.12120
• Storage Temp.: Freezer
• Solubility.: very faint turbidity in Chloroform

Purity/Quality:

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

4-Methoxyphenyl 2,6-di-O-benzyl-3,4-O-isopropylidene-b-D-galactopyranose ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 4-Methoxyphenyl 2,6-di-O-benzyl-3,4-O-isopropylidene-beta-D-galactopyranose (CAS# 159922-68-6) is a carbohydrate used in the synthesis of sulfated glycosphingolipid SM1a, a human epithelial carcinoma antigen.

Technology Process of 4-METHOXYPHENYL 2,6-DI-O-BENZYL-3,4-O-ISOPROPYLIDENE-BETA-D-GALACTOPYRANOSIDE

There total 5 articles about 4-METHOXYPHENYL 2,6-DI-O-BENZYL-3,4-O-ISOPROPYLIDENE-BETA-D-GALACTOPYRANOSIDE 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: 98.0%

benzyl bromide (100-39-0) + 4-methoxyphenyl 3,4-O-isopropylidene-β-D-galactopyranoside (159922-67-5) → 4-methoxyphenyl 2,6-di-O-benzyl-3,4-O-isopropylidene-β-D-galactopyranoside (159922-68-6)

Guidance literature:

With sodium hydride; In tetrahydrofuran; at 60 ℃; for 20h;

DOI:10.1016/S0040-4039(00)76897-3

Reference yield:

4-methoxyphenyl β-D-galactopyranoside (3150-20-7,6032-32-2,28541-75-5,85481-53-4,89731-58-8,109121-56-4,121468-39-1,12167-34-9) → 4-methoxyphenyl 2,6-di-O-benzyl-3,4-O-isopropylidene-β-D-galactopyranoside (159922-68-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 64 percent / CSA / dimethylformamide / 8 h

2: 91.3 percent / NaH / dimethylformamide / 5 h

With camphor-10-sulfonic acid; sodium hydride; In N,N-dimethyl-formamide;

Reference yield:

4-methoxyphenyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside (2872-65-3,14581-81-8,17042-40-9,84380-06-3,105260-62-6) → 4-methoxyphenyl 2,6-di-O-benzyl-3,4-O-isopropylidene-β-D-galactopyranoside (159922-68-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 100 percent / NaOMe / methanol / 1 h

2: 64 percent / CSA / dimethylformamide / 8 h

3: 91.3 percent / NaH / dimethylformamide / 5 h

With camphor-10-sulfonic acid; sodium methylate; sodium hydride; In methanol; N,N-dimethyl-formamide;

upstream raw materials:

benzyl bromide

4-methoxyphenyl 3,4-O-isopropylidene-β-D-galactopyranoside

4-methoxyphenyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside

4-methoxyphenyl β-D-galactopyranoside

Downstream raw materials:

4-methoxyphenyl 2,6-di-O-benzyl-β-D-galactopyranoside

4-methoxyphenyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-galactopyranosyl-(1->3)-2,6-di-O-benzyl-β-D-galactopyranoside

4-methoxyphenyl 4-O-benzoyl-2,6-di-O-benzyl-β-D-galactopyranoside

4-methoxyphenyl (methyl 2,3,4-tri-O-benzoyl-β-D-glucopyranuronate)-(1→3)-4-O-benzoyl-2,6-di-O-benzyl-β-D-galactopyranoside

Refernces

• 1、 Budhadev, Darshita,Mukhopadhyay, Balaram. "Chemical synthesis of a tetrasaccharide related to the exocellular polysaccharide from Rhodococcus sp. RHA1". . p. 26 - 31. Retrieved 2014/07/08.
• 2、 Belot, Frederic,Otter, Albin,Fukuda, Minoru,Hindsgaul, Ole. "Efficient synthesis of two HNK-1 related pentasaccharides". . p. 1315 - 1318. Retrieved 2007/10/03.