N-[(2S,3R,4R,5S,6R)-4-[(2R,3R,4S,5R,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-methoxyoxan-2-yl]oxy-5-hydroxy-6-(hydroxymethyl)-2-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)-2-methyloxan-2-yl]oxyoxan-3-yl]acetamide

Base Information

• Chemical Name: N-[(2S,3R,4R,5S,6R)-4-[(2R,3R,4S,5R,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-methoxyoxan-2-yl]oxy-5-hydroxy-6-(hydroxymethyl)-2-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)-2-methyloxan-2-yl]oxyoxan-3-yl]acetamide
• CAS No.: 130648-54-3
• Molecular Formula: C₂₂H₃₉NO₁₆
• Molecular Weight: 573.549
• DSSTox Substance ID: DTXSID10926848
• Mol file: 130648-54-3.mol

Synonyms:Me-Me-Galp-NAc-Glup-Galp;methyl O-(2-O-methyl-beta-galactopyranosyl)-(1-4)-O-(2-acetamido-2-deoxy-beta-glucopyranosyl)-(1-3)-beta-galactopyranoside

Chemical Property of N-[(2S,3R,4R,5S,6R)-4-[(2R,3R,4S,5R,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-methoxyoxan-2-yl]oxy-5-hydroxy-6-(hydroxymethyl)-2-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)-2-methyloxan-2-yl]oxyoxan-3-yl]acetamide

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 912.6°Cat760mmHg
• Flash Point: 505.7°C
• PSA: 270.04000
• Density: 1.59g/cm³
• LogP: -5.54470
• XLogP3: -5.1
• Hydrogen Bond Donor Count: 10
• Hydrogen Bond Acceptor Count: 16
• Rotatable Bond Count: 9
• Exact Mass: 573.22688416
• Heavy Atom Count: 39
• Complexity: 808

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)NC1C(C(C(OC1OC2(C(C(C(C(O2)CO)O)O)O)C)CO)O)OC3C(C(C(C(O3)CO)O)O)OC
• Isomeric SMILES: CC(=O)N[C@@H]1[C@H]([C@@H]([C@H](O[C@H]1O[C@]2([C@@H]([C@H]([C@H]([C@H](O2)CO)O)O)O)C)CO)O)O[C@H]3[C@@H]([C@H]([C@H]([C@H](O3)CO)O)O)OC

Technology Process of N-[(2S,3R,4R,5S,6R)-4-[(2R,3R,4S,5R,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-methoxyoxan-2-yl]oxy-5-hydroxy-6-(hydroxymethyl)-2-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)-2-methyloxan-2-yl]oxyoxan-3-yl]acetamide

There total 3 articles about N-[(2S,3R,4R,5S,6R)-4-[(2R,3R,4S,5R,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-methoxyoxan-2-yl]oxy-5-hydroxy-6-(hydroxymethyl)-2-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)-2-methyloxan-2-yl]oxyoxan-3-yl]acetamide 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: 80.0%

methyl O-(2-O-methyl-β-D-galactopyranosyl)-(1->4)-O-(2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl)-(1->3)-2,4,6-tri-O-benzyl-β-D-galactopyranoside → methyl O-(2-O-methyl-β-D-galactopyranosyl-1->4)-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1->3)-β-D-galactopyranoside (130648-54-3)

Guidance literature:

With hydrogen; palladium on activated charcoal; In acetic acid; for 48h; under 2587.7 Torr; Ambient temperature;

DOI:10.1016/0008-6215(90)80053-6

Reference yield:

methyl O-(3,4-O-isopropylidene-2-O-methyl-β-D-galactopyranosyl)-(1->4)-O-(2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl)-(1->3)-2,4,6-tri-O-benzyl-β-D-galactopyranoside → methyl O-(2-O-methyl-β-D-galactopyranosyl-1->4)-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1->3)-β-D-galactopyranoside (130648-54-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 89 percent / 60percent aq. HOAc / 2 h / 65 °C

2: 80 percent / H₂ / 10percent Pd-C / acetic acid / 48 h / 2587.7 Torr / Ambient temperature

With hydrogen; acetic acid; palladium on activated charcoal; In acetic acid;

DOI:10.1016/0008-6215(90)80053-6

Reference yield:

methyl O-(6-O-tert-butyldiphenylsilyl-3,4-O-isopropylidene-2-O-methyl-β-D-galactopyranosyl-1->4)-O-(2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl)-(1->3)-2,4,6-tri-O-benzyl-β-D-galactopyranoside → methyl O-(2-O-methyl-β-D-galactopyranosyl-1->4)-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1->3)-β-D-galactopyranoside (130648-54-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 98 percent / Bu₄NF / various solvent(s) / 3 h / Ambient temperature

2: 89 percent / 60percent aq. HOAc / 2 h / 65 °C

3: 80 percent / H₂ / 10percent Pd-C / acetic acid / 48 h / 2587.7 Torr / Ambient temperature

With tetrabutyl ammonium fluoride; hydrogen; acetic acid; palladium on activated charcoal; In acetic acid;

DOI:10.1016/0008-6215(90)80053-6

Refernces