(2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-{[(4-methoxyphenyl)ethynyl]thio}tetrahydro-2H-pyran-3,4,5-triyl triacetate

Base Information

• Chemical Name: (2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-{[(4-methoxyphenyl)ethynyl]thio}tetrahydro-2H-pyran-3,4,5-triyl triacetate
• CAS No.: 1467024-09-4
• Molecular Formula: C₂₃H₂₆O₁₀S
• Molecular Weight: 494.519
• Mol file: 1467024-09-4.mol

Synonyms:(2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-{[(4-methoxyphenyl)ethynyl]thio}tetrahydro-2H-pyran-3,4,5-triyl triacetate

Chemical Property of (2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-{[(4-methoxyphenyl)ethynyl]thio}tetrahydro-2H-pyran-3,4,5-triyl triacetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-{[(4-methoxyphenyl)ethynyl]thio}tetrahydro-2H-pyran-3,4,5-triyl triacetate

There total 4 articles about (2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-{[(4-methoxyphenyl)ethynyl]thio}tetrahydro-2H-pyran-3,4,5-triyl triacetate 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: 65.0%

tetraacetyl thioglucose (19879-84-6) + 1-bromo-2-(4-methoxyphenyl)acetylene (33675-41-1) → (2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-{[(4-methoxyphenyl)ethynyl]thio}tetrahydro-2H-pyran-3,4,5-triyl triacetate (1467024-09-4)

Guidance literature:

With 4,4'-di-tert-butyl-2,2'-bipyridine; lithium bromide; nickel dibromide; In N,N-dimethyl-formamide; at 20 ℃; for 3h; Electrochemical reaction; Inert atmosphere;

DOI:10.1039/d0cc01126f

Reference yield: 27.0%

tetraacetyl thioglucose (19879-84-6) + C21H17OS(1+)*CF3O3S(1-) → (2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-{[(4-methoxyphenyl)ethynyl]thio}tetrahydro-2H-pyran-3,4,5-triyl triacetate (1467024-09-4)

Guidance literature:

With triethylamine; In dimethyl sulfoxide; for 0.0583333h; chemoselective reaction; Flow reactor;

DOI:10.1039/d1gc01937f

Reference yield:

(4-methoxyphenylethynyl)trimethylsilane (3989-14-8) → (2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-{[(4-methoxyphenyl)ethynyl]thio}tetrahydro-2H-pyran-3,4,5-triyl triacetate (1467024-09-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: dichloromethane / 1 h / -50 °C

1.2: -50 °C / Heating

2.1: triethylamine / dimethyl sulfoxide / 0.06 h / Flow reactor

With triethylamine; In dichloromethane; dimethyl sulfoxide;

DOI:10.1039/d1gc01937f

upstream raw materials:

tetraacetyl thioglucose

1-bromo-2-(4-methoxyphenyl)acetylene

4-methoxyphenylacetylen

(4-methoxyphenylethynyl)trimethylsilane