p-tolyl 3,4,6-tri-O-acetyl-2-deoxy-2-N-(2,2,2-trichloroethoxycarbonylamino)-1-thio-β-D-galactopyranoside

Base Information

• Chemical Name: p-tolyl 3,4,6-tri-O-acetyl-2-deoxy-2-N-(2,2,2-trichloroethoxycarbonylamino)-1-thio-β-D-galactopyranoside
• CAS No.: 533927-89-8
• Molecular Formula: C₂₂H₂₆Cl₃NO₉S
• Molecular Weight: 586.875
• Mol file: 533927-89-8.mol

Synonyms:p-tolyl 3,4,6-tri-O-acetyl-2-deoxy-2-N-(2,2,2-trichloroethoxycarbonylamino)-1-thio-β-D-galactopyranoside

Chemical Property of p-tolyl 3,4,6-tri-O-acetyl-2-deoxy-2-N-(2,2,2-trichloroethoxycarbonylamino)-1-thio-β-D-galactopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of p-tolyl 3,4,6-tri-O-acetyl-2-deoxy-2-N-(2,2,2-trichloroethoxycarbonylamino)-1-thio-β-D-galactopyranoside

There total 4 articles about p-tolyl 3,4,6-tri-O-acetyl-2-deoxy-2-N-(2,2,2-trichloroethoxycarbonylamino)-1-thio-β-D-galactopyranoside 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: 80.0%

1,3,4,6-Tetra-O-acetyl-2-(2,2,2-trichloroethoxycarbonylamino)-2-deoxy-α/β-D-galactopyranose (151909-93-2) + para-thiocresol (106-45-6) → p-tolyl 3,4,6-tri-O-acetyl-2-deoxy-2-N-(2,2,2-trichloroethoxycarbonylamino)-1-thio-β-D-galactopyranoside (533927-89-8)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at 0 - 20 ℃; Inert atmosphere;

DOI:10.1021/acs.orglett.7b02271

Reference yield:

D-(+)-galactosamine hydrochloride (1772-03-8,4710-95-6,6730-09-2,14131-59-0,14131-62-5,14131-63-6,14131-65-8,14131-67-0,14257-79-5,19124-46-0,20706-90-5,91673-92-6) → p-tolyl 3,4,6-tri-O-acetyl-2-deoxy-2-N-(2,2,2-trichloroethoxycarbonylamino)-1-thio-β-D-galactopyranoside (533927-89-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: NaHCO₃ / H₂O / 2 h / 20 °C

2.1: pyridine / 20 °C

2.2: 20.76 g / BF₃*Et₂O / CH₂Cl₂ / 6 h / 20 °C

With pyridine; sodium hydrogencarbonate; In water;

DOI:10.1021/jo070585g

Reference yield:

2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-D-galactopyranose → p-tolyl 3,4,6-tri-O-acetyl-2-deoxy-2-N-(2,2,2-trichloroethoxycarbonylamino)-1-thio-β-D-galactopyranoside (533927-89-8)

Guidance literature:

Multi-step reaction with 2 steps

1: pyridine; dmap / Inert atmosphere

2: boron trifluoride diethyl etherate / dichloromethane / 0 - 20 °C / Inert atmosphere

With pyridine; dmap; boron trifluoride diethyl etherate; In dichloromethane;

DOI:10.1007/s11426-011-4449-x

upstream raw materials:

acetic anhydride

para-thiocresol

D-(+)-galactosamine hydrochloride

1,3,4,6-Tetra-O-acetyl-2-(2,2,2-trichloroethoxycarbonylamino)-2-deoxy-α/β-D-galactopyranose

Downstream raw materials:

p-tolyl 3,4,6-tri-O-acetyl-2-amino-2-deoxy-1-thio-β-D-galactopyranoside

C₅₇H₅₆Cl₃NO₁₂S

C₅₄H₅₆Cl₃NO₁₄S

p-tolyl 2-deoxy-2-trichloracetamido-1-thio-β-D-galactopyranoside