phenyl-3,4,6-tri-O-acetyl-2-acetamido-2-deoxy-1-selenenylsulfide-β-d-glucopyranoside

Base Information

• Chemical Name: phenyl-3,4,6-tri-O-acetyl-2-acetamido-2-deoxy-1-selenenylsulfide-β-d-glucopyranoside
• CAS No.: 678968-48-4
• Molecular Formula: C₂₀H₂₅NO₈SSe
• Molecular Weight: 518.446
• Mol file: 678968-48-4.mol

Synonyms:phenyl-3,4,6-tri-O-acetyl-2-acetamido-2-deoxy-1-selenenylsulfide-β-d-glucopyranoside

Chemical Property of phenyl-3,4,6-tri-O-acetyl-2-acetamido-2-deoxy-1-selenenylsulfide-β-d-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of phenyl-3,4,6-tri-O-acetyl-2-acetamido-2-deoxy-1-selenenylsulfide-β-d-glucopyranoside

There total 5 articles about phenyl-3,4,6-tri-O-acetyl-2-acetamido-2-deoxy-1-selenenylsulfide-β-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: 73.0%

2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-1-thio-β-D-glucopyranose (51450-09-0) + Phenylselenyl bromide (34837-55-3) → phenyl-3,4,6-tri-O-acetyl-2-acetamido-2-deoxy-1-selenenylsulfide-β-d-glucopyranoside (678968-48-4)

Guidance literature:

In dichloromethane; at 20 ℃; for 0.166667h; Inert atmosphere;

DOI:10.1002/anie.200704381

Reference yield: 66.0%

→ phenyl-3,4,6-tri-O-acetyl-2-acetamido-2-deoxy-1-selenenylsulfide-β-d-glucopyranoside (678968-48-4)

Guidance literature:

Reference yield: 50.0%

diphenyl diselenide (1666-13-3) + Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-chloro-tetrahydro-pyran-4-yl ester (3068-34-6) → phenyl-3,4,6-tri-O-acetyl-2-acetamido-2-deoxy-1-selenenylsulfide-β-d-glucopyranoside (678968-48-4)

Guidance literature:

Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-chloro-tetrahydro-pyran-4-yl ester; With benzyltriethylammonium tetrathiomolybdate; In acetonitrile; at 25 ℃; for 2h;

diphenyl diselenide; In acetonitrile; at 25 ℃; for 4h;

DOI:10.1016/j.carres.2014.09.005

upstream raw materials:

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

Phenylselenyl bromide

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-2-deoxy-α-D-glucopyranosyl chloride

Downstream raw materials:

N-acetyl-S-(3,4,6-tri-O-acetyl-2-acetamido-2-deoxy-β-D-glucopyranosylthio)-L-cysteine methyl ester