4-Methoxyphenyl 2,3,6-tri-O-benzyl-4-O-(2,6-di-O-benzyl-b-D-galactopyranosyl)-b-D-glucopyranoside

Base Information

• Chemical Name: 4-Methoxyphenyl 2,3,6-tri-O-benzyl-4-O-(2,6-di-O-benzyl-b-D-galactopyranosyl)-b-D-glucopyranoside
• CAS No.: 358681-61-5
• Molecular Formula: C54H58 O12
• Molecular Weight: 899.047
• DSSTox Substance ID: DTXSID90457140
• Nikkaji Number: J1.819.951C
• Wikidata: Q82279872
• Mol file: 358681-61-5.mol

Synonyms:358681-61-5;Gal[26Bn]beta(1-4)Glc[236Bn]-beta-MP;4-Methoxyphenyl 2,3,6-tri-O-benzyl-4-O-(2,6-di-O-benzyl-b-D-galactopyranosyl)-b-D-glucopyranoside;(2R,3R,4S,5R,6S)-6-[(2R,3R,4S,5R,6S)-6-(4-methoxyphenoxy)-4,5-bis(phenylmethoxy)-2-(phenylmethoxymethyl)oxan-3-yl]oxy-5-phenylmethoxy-2-(phenylmethoxymethyl)oxane-3,4-diol;Gal[26Bn]|A(1-4)Glc[236Bn]-|A-MP;4-Methoxyphenyl 4-O-(2,6-Di-O-benzyl-beta-D-galactopyranosyl)-2,3,6-tri-O-benzyl-beta-D-glucopyranoside;DTXSID90457140;MFCD11112170;HY-W145594;CS-0226020;T72359;4-Methoxyphenyl 2,3,6-tri-O-benzyl-4-O-(2,6-di-O-benzyl-beta-D-galactopyranosyl)-beta-D-glucopyranoside;4-Methoxyphenyl 2-O,3-O,6-O-tribenzyl-4-O-(2-O,6-O-dibenzyl-beta-D-galactopyranosyl)-beta-D-glucopyranoside

Chemical Property of 4-Methoxyphenyl 2,3,6-tri-O-benzyl-4-O-(2,6-di-O-benzyl-b-D-galactopyranosyl)-b-D-glucopyranoside

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 128.0 to 132.0 °C
• Refractive Index: 1.637
• Boiling Point: 949.695°C at 760 mmHg
• Flash Point: 528.157°C
• PSA: 132.76000
• Density: 1.291g/cm³
• LogP: 7.82060
• XLogP3: 7.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 12
• Rotatable Bond Count: 22
• Exact Mass: 898.39282728
• Heavy Atom Count: 66
• Complexity: 1290

Purity/Quality:

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

Gal[26Bn]β(1-4)Glc[236Bn]-β-MP >98.0%(HPLC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC=C(C=C1)OC2C(C(C(C(O2)COCC3=CC=CC=C3)OC4C(C(C(C(O4)COCC5=CC=CC=C5)O)O)OCC6=CC=CC=C6)OCC7=CC=CC=C7)OCC8=CC=CC=C8
• Isomeric SMILES: COC1=CC=C(C=C1)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)COCC3=CC=CC=C3)O[C@H]4[C@@H]([C@H]([C@H]([C@H](O4)COCC5=CC=CC=C5)O)O)OCC6=CC=CC=C6)OCC7=CC=CC=C7)OCC8=CC=CC=C8

Technology Process of 4-Methoxyphenyl 2,3,6-tri-O-benzyl-4-O-(2,6-di-O-benzyl-b-D-galactopyranosyl)-b-D-glucopyranoside

There total 4 articles about 4-Methoxyphenyl 2,3,6-tri-O-benzyl-4-O-(2,6-di-O-benzyl-b-D-galactopyranosyl)-b-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:

4-methoxyphenyl 2,6-di-O-benzyl-3,4-O-isopropylidene-β-D-galactopyranosyl(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside (717132-43-9) → p-methoxyphenyl (2,6-di-O-benzyl-β-D-galactopyranosyl)-(1→4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside (358681-61-5)

Guidance literature:

With trifluoroacetic acid; In dichloromethane;

DOI:10.1139/v02-131

Reference yield:

4-methoxyphenyl (β-D-galactopyranosyl)-(1->4)-β-D-glucopyranoside (150412-80-9) → p-methoxyphenyl (2,6-di-O-benzyl-β-D-galactopyranosyl)-(1→4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside (358681-61-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 66 percent / p-toluenesulfonic acid / dimethylformamide / 4 h / 80 °C

2: NaH / dimethylformamide / 2 h / 0 °C

3: 13 g / aq. HCl / methanol / 2 h / 50 °C

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

DOI:10.1081/CAR-120037571

Reference yield:

4-methoxyphenyl 3,4-O-isopropylidene-β-D-galactopyranosyl(1->4)-β-D-glucopyranoside (717132-42-8) → p-methoxyphenyl (2,6-di-O-benzyl-β-D-galactopyranosyl)-(1→4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside (358681-61-5)

Guidance literature:

Multi-step reaction with 2 steps

1: NaH / dimethylformamide / 2 h / 0 °C

2: 13 g / aq. HCl / methanol / 2 h / 50 °C

With hydrogenchloride; sodium hydride; In methanol; N,N-dimethyl-formamide;

DOI:10.1081/CAR-120037571

upstream raw materials:

4-methoxyphenyl 2,6-di-O-benzyl-3,4-O-isopropylidene-β-D-galactopyranosyl(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside

4-methoxyphenyl (β-D-galactopyranosyl)-(1->4)-β-D-glucopyranoside

4-methoxyphenyl 3,4-O-isopropylidene-β-D-galactopyranosyl(1->4)-β-D-glucopyranoside

benzyl chloride

Downstream raw materials:

4-methoxyphenyl 3-O-allyl-2,6-di-O-benzyl-β-D-galactopyranosyl(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside

4-methoxyphenyl 2,4,6-tri-O-benzyl-β-D-galactopyranosyl(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside

4-methoxyphenyl 2,4,6-tri-O-benzyl-β-D-xylo-hex-3-ulopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside

4-methoxyphenyl 3-O-allyl-2,4,6-tri-O-benzyl-β-D-galactopyranosyl(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside

Refernces

• 1、 Zhang, Zhiyuan,Niikura, Kenichi,Huang, Xue-Fei,Wong, Chi-Huey. "A strategy for the one-pot synthesis of sialylated oligosaccharides". . p. 1051 - 1054. Retrieved 2007/10/03.