S-phenyl 3,4,6-tri-O-acetyl-2-deoxy-β-D-arabino-thiohexopyranoside

Base Information

• Chemical Name: S-phenyl 3,4,6-tri-O-acetyl-2-deoxy-β-D-arabino-thiohexopyranoside
• CAS No.: 135700-54-8
• Molecular Formula: C₁₈H₂₂O₇S
• Molecular Weight: 382.434
• Mol file: 135700-54-8.mol

Synonyms:S-phenyl 3,4,6-tri-O-acetyl-2-deoxy-β-D-arabino-thiohexopyranoside

Chemical Property of S-phenyl 3,4,6-tri-O-acetyl-2-deoxy-β-D-arabino-thiohexopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of S-phenyl 3,4,6-tri-O-acetyl-2-deoxy-β-D-arabino-thiohexopyranoside

There total 5 articles about S-phenyl 3,4,6-tri-O-acetyl-2-deoxy-β-D-arabino-thiohexopyranoside 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: 57.0%

3,4,6-tri-O-acetyl-2-deoxy-α-D-arabino-hexopyranosyl chloride (88580-20-5) + thiophenol (108-98-5) → S-phenyl 3,4,6-tri-O-acetyl-2-deoxy-β-D-arabino-thiohexopyranoside (135700-54-8)

Guidance literature:

With triethylamine; In dichloromethane; at 20 ℃; for 1h; Inert atmosphere;

DOI:10.1002/anie.202115394

Reference yield:

1,3,4,6-tetra-O-acetyl-2-deoxy-D-glucopyranose (69515-91-9) + thiophenol (108-98-5) → S-phenyl 3,4,6-tri-O-acetyl-2-deoxy-β-D-arabino-thiohexopyranoside (135700-54-8) + thiophenyl 2-deoxy-3,4,6-tri-O-acetyl-α-D-glucopyranoside (90670-51-2)

Guidance literature:

With boron trifluoride diethyl etherate; In toluene; at 20 ℃; for 2h; Title compound not separated from byproducts;

DOI:10.1021/jm050144u

Reference yield:

thiophenol (108-98-5) + Acetic acid (2R,3S,4R)-4-acetoxy-2-acetoxymethyl-6-chloro-tetrahydro-pyran-3-yl ester (125354-45-2) → S-phenyl 3,4,6-tri-O-acetyl-2-deoxy-β-D-arabino-thiohexopyranoside (135700-54-8)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In toluene; at 20 ℃;

DOI:10.1021/jo061417b

upstream raw materials:

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

thiophenol

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

D-glucal triacetate