phenyl 2-azido-2-deoxy-3,4,6-tri-O-acetyl-1-thio-α/β-D-glucopyranoside

Base Information

• Chemical Name: phenyl 2-azido-2-deoxy-3,4,6-tri-O-acetyl-1-thio-α/β-D-glucopyranoside
• CAS No.: 183875-22-1
• Molecular Formula: C₁₈H₂₁N₃O₇S
• Molecular Weight: 423.447
• Mol file: 183875-22-1.mol

Synonyms:phenyl 2-azido-2-deoxy-3,4,6-tri-O-acetyl-1-thio-α/β-D-glucopyranoside

Chemical Property of phenyl 2-azido-2-deoxy-3,4,6-tri-O-acetyl-1-thio-α/β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of phenyl 2-azido-2-deoxy-3,4,6-tri-O-acetyl-1-thio-α/β-D-glucopyranoside

There total 5 articles about phenyl 2-azido-2-deoxy-3,4,6-tri-O-acetyl-1-thio-α/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: 95.0%

1,3,4,6-tetra-O-acetyl-2-azido-2-deoxy-D-glucopyranose (171032-74-9) + thiophenol (108-98-5) → phenyl 2-azido-2-deoxy-3,4,6-tri-O-acetyl-1-thio-α/β-D-glucopyranoside (183875-22-1)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane;

DOI:10.1016/j.tetlet.2006.10.064

Reference yield: 90.0%

phenylthiotrimethylsilane (4551-15-9) + 1,3,4,6-tetra-O-acetyl-2-azido-2-deoxy-D-glucopyranose (171032-74-9) → phenyl 2-azido-2-deoxy-3,4,6-tri-O-acetyl-1-thio-α/β-D-glucopyranoside (183875-22-1)

Guidance literature:

With zinc(II) iodide; In 1,2-dichloro-ethane; at 50 ℃;

DOI:10.1016/S0960-894X(02)01073-9

Reference yield:

2-azido-2-deoxy-D-glucose → phenyl 2-azido-2-deoxy-3,4,6-tri-O-acetyl-1-thio-α/β-D-glucopyranoside (183875-22-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 4-dimethylaminopyridine; pyridine

2: 95 percent / BF₃*OEt₂ / CH₂Cl₂

With pyridine; dmap; boron trifluoride diethyl etherate; In dichloromethane;

DOI:10.1016/j.tetlet.2006.10.064

upstream raw materials:

1,3,4,6-tetra-O-acetyl-2-azido-2-deoxy-D-glucopyranose

thiophenol

phenylthiotrimethylsilane

(+)-D-glucosamine hydrochloride

Downstream raw materials:

phenyl 2-azido-2-deoxy-1-thio-β-D-glucopyranoside

5-azido-4-benzyloxy-2-hydroxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3-ol

5-azido-2-azidomethyl-4-benzyloxy-6-phenylsulfanyl-tetrahydro-pyran-3-ol

acetic acid 5-azido-2-azidomethyl-4-benzyloxy-6-phenylsulfanyl-tetrahydro-pyran-3-yl ester