[(2R,3S,4R,5R,6S)-5-acetamido-3,4-diacetyloxy-6-sulfanyloxan-2-yl]methyl acetate

Base Information

• Chemical Name: [(2R,3S,4R,5R,6S)-5-acetamido-3,4-diacetyloxy-6-sulfanyloxan-2-yl]methyl acetate
• CAS No.: 51450-09-0
• Molecular Formula: C14H21NO8S
• Molecular Weight: 363.389
• DSSTox Substance ID: DTXSID10456392
• Nikkaji Number: J719.558C
• Mol file: 51450-09-0.mol

Synonyms:51450-09-0;[(2R,3S,4R,5R,6S)-5-acetamido-3,4-diacetyloxy-6-sulfanyloxan-2-yl]methyl acetate;2-ACETAMIDO-2-DEOXY-1-THIO-BETA-D-GLUCOPYRANOSE 3,4,6-TRIACETATE;SCHEMBL1582779;DTXSID10456392;2-(Acetylamino)-2-deoxy-1-thio-beta-D-glucopyranose 3,4,6-triacetate

Chemical Property of [(2R,3S,4R,5R,6S)-5-acetamido-3,4-diacetyloxy-6-sulfanyloxan-2-yl]methyl acetate

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.513
• Boiling Point: 527.724°C at 760 mmHg
• Flash Point: 272.958°C
• PSA: 159.52000
• Density: 1.306g/cm³
• LogP: 0.41260
• Storage Temp.: ?20°C
• XLogP3: 0.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 8
• Exact Mass: 363.09878780
• Heavy Atom Count: 24
• Complexity: 511

Purity/Quality:

99% ^*data from raw suppliers

2-ACETAMIDO-2-DEOXY-1-THIO-BETA-D-GLUCOPYRANOSE-3,4,6-TRIACETATE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)NC1C(C(C(OC1S)COC(=O)C)OC(=O)C)OC(=O)C
• Isomeric SMILES: CC(=O)N[C@@H]1[C@H]([C@@H]([C@H](O[C@H]1S)COC(=O)C)OC(=O)C)OC(=O)C

Technology Process of [(2R,3S,4R,5R,6S)-5-acetamido-3,4-diacetyloxy-6-sulfanyloxan-2-yl]methyl acetate

There total 19 articles about [(2R,3S,4R,5R,6S)-5-acetamido-3,4-diacetyloxy-6-sulfanyloxan-2-yl]methyl acetate 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: 92.0%

2-acetamido-3,4,6-tri-O-acetyl-1-S-acetyl-2-deoxy-1-thio-β-D-glucopyranoside (10043-46-6,129693-99-8,129694-00-4) → 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-1-thio-β-D-glucopyranose (51450-09-0)

Guidance literature:

With sodium hydrogencarbonate; D,L-dithiothreitol; In N,N-dimethyl-formamide; at 20 ℃;

DOI:10.1021/acs.jmedchem.9b00550

Reference yield: 91.0%

S-thiouronium 2-N-acetamido-3,4,6-tri-O-acetyl-2-deoxy-1-thio-β-D-glucopyranoside hydrochloride (51224-18-1) → 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-1-thio-β-D-glucopyranose (51450-09-0)

Guidance literature:

With potassium bisulfite; In chloroform; at 80 ℃; for 0.333333h;

DOI:10.1135/cccc19961489

Reference yield: 90.0%

→ 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-1-thio-β-D-glucopyranose (51450-09-0)

Guidance literature:

With sodium hydrogencarbonate; diothiothreitol; In N,N-dimethyl acetamide; at 20 ℃; for 1h;

upstream raw materials:

S-thiouronium 2-N-acetamido-3,4,6-tri-O-acetyl-2-deoxy-1-thio-β-D-glucopyranoside hydrochloride

2-acetamido-3,4,6-tri-O-acetyl-1-carbamoyl-2-deoxy-1-thio-β-D-glucopyranose

2-acetamido-3,4,6-tri-O-acetyl-1-S-acetyl-2-deoxy-1-thio-β-D-glucopyranoside

Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-chloro-tetrahydro-pyran-4-yl ester

Downstream raw materials:

(3,6/4,5)-6-(2-Acetamido-3,4,6-tri-O-acetyl-2-desoxy-β-D-glucopyranosylthio)-4-brom-3,5-dihydroxy-cyclohexen

triphenylmethyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-1-thio-β-D-glucopyranoside

2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-1-S-(2,4-dinitrophenyl)-1-thio-β-D-glucopyranose

diphenylmethyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-1-thio-β-D-glucopyranoside