Methyl 2-Acetamido-4-O-(2-acetamido-2-deoxy-beta-D-gluco-pyranosyl)-2-deoxy-6-O-(alpha-L-fucopyranosyl)-beta-D-glucopyranoside

Base Information

• Chemical Name: Methyl 2-Acetamido-4-O-(2-acetamido-2-deoxy-beta-D-gluco-pyranosyl)-2-deoxy-6-O-(alpha-L-fucopyranosyl)-beta-D-glucopyranoside
• CAS No.: 97242-84-7
• Molecular Formula: C₂₃H₄₀N₂O₁₅
• Molecular Weight: 584.575
• DSSTox Substance ID: DTXSID601101207
• Mol file: 97242-84-7.mol

Synonyms:97242-84-7;Methyl 2-Acetamido-4-O-(2-acetamido-2-deoxy-beta-D-gluco- pyranosyl)-2-deoxy-6-O-(alpha-L-fucopyranosyl)-beta-D-glucopyranoside;Methyl 2-acetamido-4-O-(2-acetamido-2-deoxy-b-D-glucopyranosyl)-2-deoxy-6-O-(a-L-fucopyranosyl)-b-D-glucopyranoside;N-((2R,3R,4R,5S,6R)-5-(((2S,3R,4R,5S,6R)-3-Acetamido-4,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-4-hydroxy-2-methoxy-6-((((2R,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)methyl)tetrahydro-2H-pyran-3-yl)acetamide;DTXSID601101207;Methyl 2-Acetamido-4-O-(2-acetamido-2-deoxy-|A-D-gluco- pyranosyl)-2-deoxy-6-O-(|A-L-fucopyranosyl)-|A-D-glucopyranoside;Methyl 2-acetamido-4-O-(2-acetamido-2-Deoxy-beta-d-gluco-pyranosyl)-2-deoxy-6-O-(alpha-L-fucopyranosyl)-beta-D-glucopyranoside;GlcNAc1-b-4[Fuc1-alpha-6]GlcNAc-b-O-Me;W-204152;Methyl 2-Acetamido-4-O-(2-acetamido-2-deoxy- beta -D-gluco- pyranosyl)-2-deoxy-6-O-( alpha -L-fucopyranosyl)- beta -D-glucopyranoside;Methyl 2-Acetamido-4-O-(2-acetamido-2-deoxy-b-D-gluco- pyranosyl)-2-deoxy-6-O-(a-L-fucopyranosyl)-b-D-glucopyranoside;Methyl 2-Acetamido-4-O-(2-acetamido-2-deoxy-beta-D-gluco- pyranosyl)-2-deoxy-6-O-(alpha-L-fucopyranosyl)-beta-;Methyl O-2-(acetylamino)-2-deoxy-beta-D-glucopyranosyl-(1-->4)-O-[6-deoxy-alpha-L-galactopyranosyl-(1-->6)]-2-(acetylamino)-2-deoxy-beta-D-glucopyranoside;N-[(2S,3R,4R,5S,6R)-2-[(2R,3S,4R,5R,6R)-5-acetamido-4-hydroxy-6-methoxy-2-[[(2R,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-3-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide

Chemical Property of Methyl 2-Acetamido-4-O-(2-acetamido-2-deoxy-beta-D-gluco-pyranosyl)-2-deoxy-6-O-(alpha-L-fucopyranosyl)-beta-D-glucopyranoside

Chemical Property:

• Melting Point: 275掳C dec.
• Boiling Point: 963.9oC at 760 mmHg
• Flash Point: 536.7oC
• PSA: 255.19000
• Density: 1.52g/cm3
• LogP: -4.82190
• Storage Temp.: -20°C Freezer
• Solubility.: Water (Slightly)
• XLogP3: -5.3
• Hydrogen Bond Donor Count: 9
• Hydrogen Bond Acceptor Count: 15
• Rotatable Bond Count: 9
• Exact Mass: 584.24286857
• Heavy Atom Count: 40
• Complexity: 853

Purity/Quality:

95% ^*data from raw suppliers

Methyl2-Acetamido-4-O-(2-acetamido-2-deoxy-β-D-gluco-pyranosyl)-2-deoxy-6-O-(α-L-fucopyranosyl)-β-D-glucopyranoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1C(C(C(C(O1)OCC2C(C(C(C(O2)OC)NC(=O)C)O)OC3C(C(C(C(O3)CO)O)O)NC(=O)C)O)O)O
• Isomeric SMILES: C[C@H]1[C@H]([C@H]([C@@H]([C@@H](O1)OC[C@@H]2[C@H]([C@@H]([C@H]([C@@H](O2)OC)NC(=O)C)O)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)NC(=O)C)O)O)O
• Uses: Methyl 2-Acetamido-4-O-(2-acetamido-2-deoxy-β-D-gluco- pyranosyl)-2-deoxy-6-O-(α-L-fucopyranosyl)-β-D-glucopyranoside (cas# 97242-84-7) is a compound useful in organic synthesis.

Technology Process of Methyl 2-Acetamido-4-O-(2-acetamido-2-deoxy-beta-D-gluco-pyranosyl)-2-deoxy-6-O-(alpha-L-fucopyranosyl)-beta-D-glucopyranoside

There total 14 articles about Methyl 2-Acetamido-4-O-(2-acetamido-2-deoxy-beta-D-gluco-pyranosyl)-2-deoxy-6-O-(alpha-L-fucopyranosyl)-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:

methyl-2-desoxy-2-phthalimido-β-D-glucopyranoside (76101-14-9) → methyl 2-acetamido-4-O-(2'-acetamido-2'-deoxy-β-D-glucopyranosyl)-2-deoxy-6-O-(α-L-fucopyranosyl)-β-D-glucopyranoside (97242-84-7)

Guidance literature:

Multi-step reaction with 8 steps

1: 85 percent / p-toluenesulphonic acid / acetonitrile

2: 86 percent / sodium hydride / 1,2-dimethoxy-ethane

3: 95 percent / molecular sieves, sodium cyanoborohydride, HCl / tetrahydrofuran; diethyl ether / 1 h / Ambient temperature

4: 46 percent / collidine, silver triflate / nitromethane / 1.) -25 deg C, 4 h; 2.) rt, overnight

5: 1.) hydrazine hydrate / 1.) 95percent aqueous ethanol, reflux, 30 min; 2.) pyridine, rt, overnight

6: 87 percent / hydrogen / palladium-on-carbon / methanol / 16 h

7: 65 percent / tetraethylammonium bromide, molecular sieves / CH₂Cl₂; dimethylformamide / 16 h / Ambient temperature

8: 1.) hydrogen; 2.) sodium methoxide / 1.) palladium-on-carbon / 1.) methanol, 16 h; 2.) methanol

With 2,3,5-trimethyl-pyridine; hydrogenchloride; molecular sieve; tetraethylammonium bromide; hydrogen; sodium methylate; silver trifluoromethanesulfonate; sodium hydride; sodium cyanoborohydride; toluene-4-sulfonic acid; hydrazine hydrate; palladium on activated charcoal; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; diethyl ether; nitromethane; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1139/v85-182

Reference yield:

perbenzyl fucosyl bromide (33639-77-9) → methyl 2-acetamido-4-O-(2'-acetamido-2'-deoxy-β-D-glucopyranosyl)-2-deoxy-6-O-(α-L-fucopyranosyl)-β-D-glucopyranoside (97242-84-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 65 percent / tetraethylammonium bromide, molecular sieves / CH₂Cl₂; dimethylformamide / 16 h / Ambient temperature

2: 1.) hydrogen; 2.) sodium methoxide / 1.) palladium-on-carbon / 1.) methanol, 16 h; 2.) methanol

With molecular sieve; tetraethylammonium bromide; hydrogen; sodium methylate; palladium on activated charcoal; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1139/v85-182

Reference yield:

methyl 3,6-di-O-benzyl-2-deoxy-2-N-phthalimido-β-D-glucopyranoside (97242-79-0) → methyl 2-acetamido-4-O-(2'-acetamido-2'-deoxy-β-D-glucopyranosyl)-2-deoxy-6-O-(α-L-fucopyranosyl)-β-D-glucopyranoside (97242-84-7)

Guidance literature:

Multi-step reaction with 5 steps

1: 46 percent / collidine, silver triflate / nitromethane / 1.) -25 deg C, 4 h; 2.) rt, overnight

2: 1.) hydrazine hydrate / 1.) 95percent aqueous ethanol, reflux, 30 min; 2.) pyridine, rt, overnight

3: 87 percent / hydrogen / palladium-on-carbon / methanol / 16 h

4: 65 percent / tetraethylammonium bromide, molecular sieves / CH₂Cl₂; dimethylformamide / 16 h / Ambient temperature

5: 1.) hydrogen; 2.) sodium methoxide / 1.) palladium-on-carbon / 1.) methanol, 16 h; 2.) methanol

With 2,3,5-trimethyl-pyridine; molecular sieve; tetraethylammonium bromide; hydrogen; sodium methylate; silver trifluoromethanesulfonate; hydrazine hydrate; palladium on activated charcoal; In methanol; nitromethane; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1139/v85-182

upstream raw materials:

Acetic acid (2R,3R,4R,5S,6R)-3-acetylamino-5-((2S,3R,4R,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-2-yloxy)-2-methoxy-6-((2R,3S,4R,5R,6S)-3,4,5-triacetoxy-6-methyl-tetrahydro-pyran-2-yloxymethyl)-tetrahydro-pyran-4-yl ester

methyl 2-acetamido-4-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-6-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-2-deoxy-β-D-glucopyranoside

methyl-2-desoxy-2-phthalimido-β-D-glucopyranoside

perbenzyl fucosyl bromide

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