Methyl fucopyranosyl(1-4)-2-acetamido-2-deoxyglucopyranoside

Base Information

• Chemical Name: Methyl fucopyranosyl(1-4)-2-acetamido-2-deoxyglucopyranoside
• CAS No.: 153756-68-4
• Molecular Formula: C₁₅H₂₇NO₁₀
• Molecular Weight: 381.38
• DSSTox Substance ID: DTXSID30165419
• Nikkaji Number: J1.362.383J
• Wikidata: Q83034583
• Mol file: 153756-68-4.mol

Synonyms:alpha-D-Fuc(1-4)-beta-D-GlcNAc-OMe;Fuc(1-4)GlcNAc-OMe;methyl alpha-D-fucopyranosyl(1-4)-2-acetamido-2-deoxy-beta-D-glucopyranoside;methyl fucopyranosyl(1-4)-2-acetamido-2-deoxyglucopyranoside

Chemical Property of Methyl fucopyranosyl(1-4)-2-acetamido-2-deoxyglucopyranoside

Chemical Property:

• Vapor Pressure: 2.96E-22mmHg at 25°C
• Boiling Point: 693.6°Cat760mmHg
• PKA: 12.77±0.70(Predicted)
• Flash Point: 373.3°C
• PSA: 170.66000
• Density: 1.46g/cm³
• LogP: -2.73140
• XLogP3: -3.7
• Hydrogen Bond Donor Count: 6
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 5
• Exact Mass: 381.16349606
• Heavy Atom Count: 26
• Complexity: 479

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1C(C(C(C(O1)OC2C(OC(C(C2O)NC(=O)C)OC)CO)O)O)O
• Isomeric SMILES: C[C@@H]1[C@@H]([C@@H]([C@H]([C@H](O1)O[C@@H]2[C@H](O[C@H]([C@@H]([C@H]2O)NC(=O)C)OC)CO)O)O)O

Technology Process of Methyl fucopyranosyl(1-4)-2-acetamido-2-deoxyglucopyranoside

There total 20 articles about Methyl fucopyranosyl(1-4)-2-acetamido-2-deoxyglucopyranoside 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: 93.0%

methyl O-(2,3,4-tri-O-acetyl-6-deoxy-β-D-galactopyranosyl)-(1<*>4)-3,6-di-O-acetyl-2-acetamido-2-deoxy-β-D-glucopyranoside (152501-24-1) → methyl O-(6-deoxy-β-D-galactopyranosyl)-(1<*>4)-2-acetamido-2-deoxy-β-D-glucopyranoside (153756-68-4)

Guidance literature:

With sodium methylate; In methanol; for 3h; Ambient temperature;

DOI:10.1016/0008-6215(93)84251-Z

Reference yield:

N-[(2R,3R,4R,5S,6R)-4-Hydroxy-6-hydroxymethyl-2-methoxy-5-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl]-acetamide → Methyl 2-acetamido-2-deoxy-4-O-(α-L-fucopyranosyl)-β-D-glucopyranoside (131545-08-9,153756-68-4)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; under 760 Torr; Yield given; Ambient temperature;

Reference yield:

methyl O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1<*>4)-3,6-di-O-acetyl-2-azido-2-deoxy-β-D-glucopyranoside (91852-13-0) → methyl O-(6-deoxy-β-D-galactopyranosyl)-(1<*>4)-2-acetamido-2-deoxy-β-D-glucopyranoside (153756-68-4)

Guidance literature:

Multi-step reaction with 13 steps

1: H₂ / Pd/C / ethyl acetate / 12 h

2: 8.96 g / pyridine / 2 h

3: 5.2 g / NaOMe / methanol; CH₂Cl₂ / 2 h / Ambient temperature

4: camphorsulfonic acid / dimethylformamide / 2 h / 50 °C

5: DMAP / pyridine

6: 98 percent / 60percent aq.AcOH / 2 h / 90 °C

7: imidazole / dimethylformamide / 0.3 h / Ambient temperature

8: pyridine

9: 76 percent / 60percent aq.AcOH / 0.5 h / 90 °C

10: 77 percent / 4-dimethylaminopyridine, pyridine / 2 h / 50 °C

11: NaI / 1,2-dimethoxy-ethane / 12 h / 100 °C

12: Bu₃SnH, AIBN / 1,2-dimethoxy-ethane / 18 h / 100 °C

13: 93 percent / NaOMe / methanol / 3 h / Ambient temperature

With pyridine; 1H-imidazole; dmap; 2,2'-azobis(isobutyronitrile); camphor-10-sulfonic acid; hydrogen; tri-n-butyl-tin hydride; sodium methylate; acetic acid; sodium iodide; palladium on activated charcoal; In pyridine; methanol; 1,2-dimethoxyethane; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1016/0008-6215(93)84251-Z

upstream raw materials:

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

Methyl 3,6-di-O-acetyl-2-deoxy-2-phthalimido-4-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-β-D-glucopyranoside

Ethyl 3,6-di-O-acetyl-2-deoxy-2-phthalimido-1-thio-4-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-β-D-glucopyranoside

methyl O-(2,3,4-tri-O-acetyl-6-deoxy-β-D-galactopyranosyl)-(1<*>4)-3,6-di-O-acetyl-2-acetamido-2-deoxy-β-D-glucopyranoside

Refernces

• 1、 Peters, Thomas,Weimar, Thomas. "Improved Synthesis of α-L-Fuc(1->4)-β-D-GlcNAc and α-L-Fuc(1->6)-β-D-GlcNAc Building Blocks: A Convergent Strategy Employing 4-O->6-O Acetyl Migration; NOE Data of the Protected α-1,4-Linked Disaccharide". . p. 237 - 242. Retrieved 2007/10/02.