4-Methoxyphenyl 2,4,6-Tri-O-acetyl-3-O-benzyl-beta-D-glucopyranoside

Base Information

• Chemical Name: 4-Methoxyphenyl 2,4,6-Tri-O-acetyl-3-O-benzyl-beta-D-glucopyranoside
• CAS No.: 303127-79-9
• Molecular Formula: C26H30 O10
• Molecular Weight: 502.51
• DSSTox Substance ID: DTXSID10445584
• Wikidata: Q82264052
• Mol file: 303127-79-9.mol

Synonyms:303127-79-9;4-Methoxyphenyl 2,4,6-Tri-O-acetyl-3-O-benzyl-beta-D-glucopyranoside;(2R,3R,4S,5R,6S)-2-(Acetoxymethyl)-4-(benzyloxy)-6-(4-methoxyphenoxy)tetrahydro-2H-pyran-3,5-diyl diacetate;CID 10839164;[(2R,3R,4S,5R,6S)-3,5-diacetyloxy-6-(4-methoxyphenoxy)-4-phenylmethoxyoxan-2-yl]methyl acetate;DTXSID10445584;MolPort-035-784-663;MFCD08276396;AS-73158;CS-0226014;M1642;T72259;A876229;J-017900;4-Methoxyphenyl 2,4,6-Tri-O-acetyl-3-O-benzyl-|A-D-glucopyranoside;beta-D-Glucopyranoside, 4-methoxyphenyl 3-O-(phenylmethyl)-, 2,4,6-triacetate;(2R,3R,4S,5R,6S)-2-(Acetoxymethyl)-4-(benzyloxy)-6-(4-methoxyphenoxy)tetrahydro-2H-pyran-3,5-diyldiacetate;[(2R,3R,4S,5R,6S)-3,5-BIS(ACETYLOXY)-4-(BENZYLOXY)-6-(4-METHOXYPHENOXY)OXAN-2-YL]METHYL ACETATE

Chemical Property of 4-Methoxyphenyl 2,4,6-Tri-O-acetyl-3-O-benzyl-beta-D-glucopyranoside

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 160 °C
• Refractive Index: 1.555
• Boiling Point: 597.361°C at 760 mmHg
• Flash Point: 253.558°C
• PSA: 115.82000
• Density: 1.273g/cm³
• LogP: 2.81080
• Storage Temp.: Freezer
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 13
• Exact Mass: 502.18389715
• Heavy Atom Count: 36
• Complexity: 714

Purity/Quality:

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

4-Methoxyphenyl 2,4,6-Tri-O-acetyl-3-O-benzyl-β-D-glucopyranoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OCC1C(C(C(C(O1)OC2=CC=C(C=C2)OC)OC(=O)C)OCC3=CC=CC=C3)OC(=O)C
• Isomeric SMILES: CC(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)OC2=CC=C(C=C2)OC)OC(=O)C)OCC3=CC=CC=C3)OC(=O)C
• Uses: 4-Methoxyphenyl 2,4,6-tri-o-acetyl-3-o-benzyl-beta-d-glucopyranoside (CAS# 303127-79-9) is a useful carbohydrate building block, used in the synthesis of β-D-GlcpA(2SO4)-(1 →3)-D-GalpNAc(6SO4), the disaccharide repeating unit of shark cartilage.

Technology Process of 4-Methoxyphenyl 2,4,6-Tri-O-acetyl-3-O-benzyl-beta-D-glucopyranoside

There total 1 articles about 4-Methoxyphenyl 2,4,6-Tri-O-acetyl-3-O-benzyl-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: 69.0%

4-methoxy-phenol (150-76-5) + 1,2,4,6-tetra-O-acetyl-3-O-benzyl-β-D-glucopyranose (39686-94-7,56632-47-4,65827-58-9,99202-62-7,99202-66-1,103082-79-7,103703-00-0,103703-01-1,118711-49-2,127853-23-0,139563-66-9) → 4-Methoxyphenyl 2,4,6-tri-O-acetyl-3-O-benzyl-β-D-glucopyranoside (303127-79-9)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; In dichloromethane; at 0 ℃; for 2h;

DOI:10.1039/b002835p

Reference yield: 89.0%

sodium methylate (124-41-4) + 4-Methoxyphenyl 2,4,6-tri-O-acetyl-3-O-benzyl-β-D-glucopyranoside (303127-79-9) → 4-Methoxyphenyl 3-O-benzyl-β-D-glucopyranoside (303127-80-2)

Guidance literature:

In methanol; at 20 ℃; for 16h;

DOI:10.1039/b002835p

Reference yield:

4-Methoxyphenyl 2,4,6-tri-O-acetyl-3-O-benzyl-β-D-glucopyranoside (303127-79-9) → p-methoxyphenyl 3-O-benzyl-4,6-di-O-benzylidene-β-D-glucopyranoside (303127-81-3)

Guidance literature:

Multi-step reaction with 2 steps

1: NaOMe / methanol / 3 h

2: 810 mg / p-toluenesulfonic acid / acetonitrile / 15 h

With sodium methylate; toluene-4-sulfonic acid; In methanol; acetonitrile;

DOI:10.1016/j.tet.2004.06.037

upstream raw materials:

4-methoxy-phenol

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

Downstream raw materials:

4-Methoxyphenyl 3-O-benzyl-β-D-glucopyranoside

p-methoxyphenyl 3-O-benzyl-4,6-di-O-benzylidene-β-D-glucopyranoside

tert-butyldimethylsilyl 3-O-benzyl-2-O-pivaloyl-β-D-glucopyranoside

p-methoxyphenyl 3-O-benzyl-2-O-pivaloyl-β-D-glucopyranoside

Refernces