N-[5-[3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,4-dihydroxy-6-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxymethyl]oxan-3-yl]acetamide

Base Information

• Chemical Name: N-[5-[3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,4-dihydroxy-6-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxymethyl]oxan-3-yl]acetamide
• CAS No.: 79365-98-3
• Molecular Formula: C₂₂H₃₈N₂O₁₅
• Molecular Weight: 570.548
• DSSTox Substance ID: DTXSID70412131
• Mol file: 79365-98-3.mol

Synonyms:79365-98-3;N-[5-[3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,4-dihydroxy-6-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxymethyl]oxan-3-yl]acetamide;DTXSID70412131

Chemical Property of N-[5-[3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,4-dihydroxy-6-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxymethyl]oxan-3-yl]acetamide

Chemical Property:

• PSA: 273.17000
• LogP: -4.57720
• Storage Temp.: 2-8°C
• XLogP3: -5.8
• Hydrogen Bond Donor Count: 10
• Hydrogen Bond Acceptor Count: 15
• Rotatable Bond Count: 8
• Exact Mass: 570.22721851
• Heavy Atom Count: 39
• Complexity: 837

Purity/Quality:

97% ^*data from raw suppliers

6-O-ALPHA-L-FUCOPYRANOSYL-N,N'-DIACETYLCHITOBIOSE 95.00% ^*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)O)NC(=O)C)O)OC3C(C(C(C(O3)CO)O)O)NC(=O)C)O)O)O

Technology Process of N-[5-[3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,4-dihydroxy-6-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxymethyl]oxan-3-yl]acetamide

There total 9 articles about N-[5-[3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,4-dihydroxy-6-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxymethyl]oxan-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: 84.0%

N,N'-diacetylchitobiose (14200-67-0,18422-28-1,34147-27-8,35991-83-4,109957-89-3,109957-93-9,119719-43-6,125760-94-3,141725-02-2,145841-62-9,148682-80-8) + guanosine-5'-diphospho-β-L-fucose (15839-70-0) → 6-O-α-L-fucopyranosyl-di-N-acetylchitobiose (79365-98-3,79391-05-2)

Guidance literature:

N,N'-diacetylchitobiose; guanosine-5'-diphospho-β-L-fucose; With α-1,6-FucT; manganese(ll) chloride; In various solvent(s); for 24h; pH=7.7;

With pyridine; 1-(Trimethylsilyl)imidazole; In various solvent(s); at 60 ℃; for 0.5h; Further stages.;

DOI:10.1002/1521-3765(20010601)7:11<2390::AID-CHEM23900>3.0.CO;2-0

Reference yield:

chitobiose octaacetate (117467-63-7) → 6-O-α-L-fucopyranosyl-di-N-acetylchitobiose (79365-98-3,79391-05-2)

Guidance literature:

Multi-step reaction with 6 steps

1: 420 mg / HCl / acetic acid; acetic anhydride / 60 h / Ambient temperature

2: Ag₂CO₃ / 48 h / Ambient temperature

3: sodium methoxide / methanol / 4 h / Ambient temperature

4: 73 percent / p-toluenesulfonic acid monohydrate / acetonitrile; dimethylformamide / Ambient temperature

5: 1.) tetraethylammonium bromide, 4 Angstroem molecular sieves / 1.) CH₂Cl₂, DMF, 0.5 h, 2.) CH₂Cl₂, 19 h

6: H₂ / 10percent Pd/C / acetic acid; methanol

With hydrogenchloride; 4 A molecular sieve; tetraethylammonium bromide; hydrogen; sodium methylate; toluene-4-sulfonic acid; silver carbonate; palladium on activated charcoal; In methanol; acetic anhydride; acetic acid; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1139/v90-148

Reference yield:

benzyl 2-acetamido-4-O-(2'-acetamido-4',6'-benzylidene-2'-deoxy-β-D-glucopyranosyl)-2-deoxy-6-O-(2'',3'',4''-tri-O-benzyl-α-L-fucopyranosyl)-β-D-glucopyranoside (129579-89-1) → 6-O-α-L-fucopyranosyl-di-N-acetylchitobiose (79365-98-3,79391-05-2)

Guidance literature:

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

DOI:10.1139/v90-148

upstream raw materials:

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

N,N'-diacetylchitobiose

guanosine-5'-diphospho-β-L-fucose

benzyl 2-acetylamino-4-O-(2-acetylamino-2-deoxy-β-D-glucopyranosyl)-2-deoxy-β-D-glucopyranoside