Propionyl 3,4,6-Tri-O-acetyl-2-acetamido-2-deoxy--D-thiogalactopyranoside

Base Information

• Chemical Name: Propionyl 3,4,6-Tri-O-acetyl-2-acetamido-2-deoxy--D-thiogalactopyranoside
• CAS No.: 936026-72-1
• Molecular Formula: C₁₇H₂₅NO₁₀S
• Molecular Weight: 435.452
• Mol file: 936026-72-1.mol

Synonyms:Propionyl 3,4,6-Tri-O-acetyl-2-acetamido-2-deoxy--D-thiogalactopyranoside;3-[[3,4,6-Tri-O-acetyl-2-(acetylaMino)-2-deoxy-α-D-galactopyranosyl]thio]propanoic Acid

Chemical Property of Propionyl 3,4,6-Tri-O-acetyl-2-acetamido-2-deoxy--D-thiogalactopyranoside

Chemical Property:

• PSA: 183.32000
• LogP: 0.69070

Purity/Quality:

98% ^*data from raw suppliers

Propionyl3,4,6-Tri-O-acetyl-2-acetamido-2-deoxy-β-D-thiogalactopyranoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Propionyl 3,4,6-Tri-O-acetyl-2-acetamido-2-deoxy-β-D-thiogalactopyranoside (cas# 936026-72-1) is a compound useful in organic synthesis.

Technology Process of Propionyl 3,4,6-Tri-O-acetyl-2-acetamido-2-deoxy--D-thiogalactopyranoside

There total 4 articles about Propionyl 3,4,6-Tri-O-acetyl-2-acetamido-2-deoxy--D-thiogalactopyranoside 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: 88.0%

β-Propiolactone (57-57-8) + 1-thio-2-N-acetylamino-3,4,6-tri-O-acetyl-1,2-dideoxy-α-D-galactopyranose (434942-45-7) → S-(2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-α-D-galactopyranosyl)-3-thiopropionic acid (936026-72-1)

Guidance literature:

With sodium hexamethyldisilazane; In N,N-dimethyl-formamide; at 20 ℃; for 24h;

DOI:10.1021/jo0110909

Reference yield: 70.0%

3-mercaptopropionic acid (107-96-0) + 2-acetamido-1,3,4,6-tetra-O-acetyl-2-deoxy-β-D-galactopyranose (3006-60-8) → 3-(((2S,3R,4R,5R,6R)-3-acetamido-4,5-diacetoxy-6-(acetoxymethyl)tetrahydro-2H-pyran-2-yl)thio)propionic acid (936026-72-1)

Guidance literature:

With tin(IV) chloride; In dichloromethane; at 60 ℃; for 18h;

Reference yield:

(3aR,5R,6R,7R,7aR)-5-(acetoxymethyl)-6,7-diacetoxy-2-methyl-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole (67145-37-3) → S-(2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-α-D-galactopyranosyl)-3-thiopropionic acid (936026-72-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 100 percent / trifluoroacetic acid / methanol; H₂O

2: 88 percent / sodium bis(trimethylsilyl)amide / dimethylformamide / 24 h / 20 °C

With sodium hexamethyldisilazane; trifluoroacetic acid; In methanol; water; N,N-dimethyl-formamide;

DOI:10.1021/jo0110909

upstream raw materials:

β-Propiolactone

1-thio-2-N-acetylamino-3,4,6-tri-O-acetyl-1,2-dideoxy-α-D-galactopyranose

(3aR,5R,6R,7R,7aR)-5-(acetoxymethyl)-6,7-diacetoxy-2-methyl-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole

2-acetamido-1,3,4,6-tetra-O-acetyl-2-deoxy-β-D-galactopyranose

Refernces

• 1、 -. "CLEARING AGENT". Paragraph 0085-0087. . Retrieved 2020/01/08.