phenyl 2,3,6-tri-O-acetyl-4-deoxy-1-thio-β-D-xylo-hexoside

Base Information

• Chemical Name: phenyl 2,3,6-tri-O-acetyl-4-deoxy-1-thio-β-D-xylo-hexoside
• CAS No.: 849132-36-1
• Molecular Formula: C₁₈H₂₂O₇S
• Molecular Weight: 382.434
• Mol file: 849132-36-1.mol

Synonyms:phenyl 2,3,6-tri-O-acetyl-4-deoxy-1-thio-β-D-xylo-hexoside

Chemical Property of phenyl 2,3,6-tri-O-acetyl-4-deoxy-1-thio-β-D-xylo-hexoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of phenyl 2,3,6-tri-O-acetyl-4-deoxy-1-thio-β-D-xylo-hexoside

There total 11 articles about phenyl 2,3,6-tri-O-acetyl-4-deoxy-1-thio-β-D-xylo-hexoside 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: 83.0%

tetra-O-acetyl-4-deoxy-α-D-xylo-hexopyranose (50705-20-9) + thiophenol (108-98-5) → phenyl 2,3,6-tri-O-acetyl-4-deoxy-1-thio-β-D-xylo-hexoside (849132-36-1)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at 20 ℃; for 2h;

DOI:10.1016/j.tetasy.2004.12.004

Reference yield: 73.0%

Acetic acid (2S,3R,4S,5S,6R)-3-acetoxy-6-acetoxymethyl-5-phenoxythiocarbonyloxy-2-phenylsulfanyl-tetrahydro-pyran-4-yl ester (849132-35-0) → phenyl 2,3,6-tri-O-acetyl-4-deoxy-1-thio-β-D-xylo-hexoside (849132-36-1)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In toluene; at 60 ℃; for 4h;

DOI:10.1016/j.tetasy.2004.12.004

Reference yield:

methyl 4-deoxy-α-D-xylo-hexopyranoside (13241-00-4) → phenyl 2,3,6-tri-O-acetyl-4-deoxy-1-thio-β-D-xylo-hexoside (849132-36-1)

Guidance literature:

Multi-step reaction with 3 steps

1: pyridine

2: H₂SO₄

3: 83 percent / boron trifluoride diethyl etherate / CH₂Cl₂ / 2 h / 20 °C

With pyridine; sulfuric acid; boron trifluoride diethyl etherate; In dichloromethane;

DOI:10.1016/j.tetasy.2004.12.004

upstream raw materials:

tetra-O-acetyl-4-deoxy-α-D-xylo-hexopyranose

thiophenol

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

methyl 2,3,6-tri-O-benzoyl-α-D-galactopyranoside

Refernces

• 1、 Stick, Robert V.,Stubbs, Keith A.. "From glycoside hydrolases to thioglycoligases: The synthesis of thioglycosides". . p. 321 - 335. Retrieved 2007/10/03.