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

Base Information

• Chemical Name: triphenylmethyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-1-thio-β-D-glucopyranoside
• CAS No.: 91288-33-4
• Molecular Formula: C₃₃H₃₅NO₈S
• Molecular Weight: 605.709
• Mol file: 91288-33-4.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 4 articles about triphenylmethyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-1-thio-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: 90.0%

triphenylmethanethiol (3695-77-0) + Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-chloro-tetrahydro-pyran-4-yl ester (3068-34-6) → triphenylmethyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-1-thio-β-D-glucopyranoside (91288-33-4)

Guidance literature:

With potassium tert-butylate; In N,N-dimethyl-formamide; for 0.25h; Inert atmosphere;

DOI:10.1021/acs.orglett.9b02811

Reference yield: 42.0%

2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-1-thio-β-D-glucopyranose (51450-09-0) + trityl chloride (76-83-5) → triphenylmethyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-1-thio-β-D-glucopyranoside (91288-33-4)

Guidance literature:

In pyridine; for 96h; Ambient temperature;

DOI:10.1016/0008-6215(84)85124-1

Reference yield:

S-thiouronium 2-N-acetamido-3,4,6-tri-O-acetyl-2-deoxy-1-thio-β-D-glucopyranoside hydrochloride (51224-18-1) → triphenylmethyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-1-thio-β-D-glucopyranoside (91288-33-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 62 percent / potassium pyrosulfite / H₂O; CHCl₃ / 1.) 85 deg C, 2o min; 2.) rt, 0.5 h.

2: 42 percent / pyridine / 96 h / Ambient temperature

With potassium disulphite; In pyridine; chloroform; water;

DOI:10.1016/0008-6215(84)85124-1

upstream raw materials:

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

trityl chloride

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

Downstream raw materials:

triphenylmethyl 2-acetamido-2-deoxy-1-thio-β-D-glucopyranoside

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