(3R,5R)-1,3,4,5-Tetraacetoxy-cyclohexanecarboxylic acid 2-thioxo-2H-pyridin-1-yl ester

Base Information

• Chemical Name: (3R,5R)-1,3,4,5-Tetraacetoxy-cyclohexanecarboxylic acid 2-thioxo-2H-pyridin-1-yl ester
• CAS No.: 89031-75-4
• Molecular Formula: C₂₀H₂₃NO₁₀S
• Molecular Weight: 469.469
• Mol file: 89031-75-4.mol

Synonyms:

Chemical Property of (3R,5R)-1,3,4,5-Tetraacetoxy-cyclohexanecarboxylic acid 2-thioxo-2H-pyridin-1-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,5R)-1,3,4,5-Tetraacetoxy-cyclohexanecarboxylic acid 2-thioxo-2H-pyridin-1-yl ester

There total 2 articles about (3R,5R)-1,3,4,5-Tetraacetoxy-cyclohexanecarboxylic acid 2-thioxo-2H-pyridin-1-yl ester 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:

(-)-1,3,4,5-Tetra-O-acetylquinic acid (23804-28-6,32469-24-2,62445-00-5) → (3R,5R)-1,3,4,5-Tetraacetoxy-cyclohexanecarboxylic acid 2-thioxo-2H-pyridin-1-yl ester (89031-75-4)

Guidance literature:

Multi-step reaction with 2 steps

1: oxalylchloride / DMF / benzene / 2 h / Ambient temperature

2: DMAP / toluene / 2 h / 110 °C

With Chloro-oxo-acetic acid; dmap; N,N-dimethyl-formamide; In toluene; benzene;

DOI:10.1016/S0040-4020(01)97173-X

Reference yield:

2-mercaptopyridine-1-oxide sodium salt (3811-73-2) + Acetic acid (3R,5R)-3,4,5-triacetoxy-1-chlorocarbonyl-cyclohexyl ester (92651-21-3,92822-51-0,95463-24-4) → (3R,5R)-1,3,4,5-Tetraacetoxy-cyclohexanecarboxylic acid 2-thioxo-2H-pyridin-1-yl ester (89031-75-4)

Guidance literature:

dmap; In toluene; at 110 ℃; for 2h;

DOI:10.1016/S0040-4020(01)97173-X

Reference yield:

(3R,5R)-1,3,4,5-Tetraacetoxy-cyclohexanecarboxylic acid 2-thioxo-2H-pyridin-1-yl ester (89031-75-4) → 1β,2β,3α,5αβ-tetraacetoxycyclohexane (66325-66-4,89025-63-8,92298-56-1)

Guidance literature:

With tri-n-butyl-tin hydride; 2,2'-azobis(isobutyronitrile); In toluene; for 3h; Yield given; adding 15 min;

DOI:10.1016/S0040-4020(01)97173-X

upstream raw materials:

2-mercaptopyridine-1-oxide sodium salt

Acetic acid (3R,5R)-3,4,5-triacetoxy-1-chlorocarbonyl-cyclohexyl ester

(-)-1,3,4,5-Tetra-O-acetylquinic acid

Downstream raw materials:

1β,2β,3α,5αβ-tetraacetoxycyclohexane

Refernces