2,3,4,6-TETRA-O-ACETYL-ALPHA-D-GALACTOPYRANOSYL CHLORIDE

Base Information

• Chemical Name: 2,3,4,6-TETRA-O-ACETYL-ALPHA-D-GALACTOPYRANOSYL CHLORIDE
• CAS No.: 14227-87-3
• Molecular Formula: C14H19 Cl O9
• Molecular Weight: 366.752
• Mol file: 14227-87-3.mol

Synonyms:Galactopyranosylchloride, tetraacetate, a-D- (8CI); a-D-Galactopyranosylchloride, tetraacetate (9CI); 2,3,4,6-Tetra-O-acetyl-a-D-galactopyranosyl chloride

Chemical Property of 2,3,4,6-TETRA-O-ACETYL-ALPHA-D-GALACTOPYRANOSYL CHLORIDE

Chemical Property:

• Melting Point: 78-79 °C(Solv: ligroine (8032-32-4))
• Boiling Point: 406.4±45.0 °C(Predicted)
• PSA: 114.43000
• Density: 1.33±0.1 g/cm3(Predicted)
• LogP: 0.30830
• Solubility.: Chloroform, Dichloromethane, Ethyl Acetate

Purity/Quality:

98%Min ^*data from raw suppliers

2,3,4,6-Tetra-O-acetyl-α-D-galactopyranosyl Chloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 2,3,4,6-Tetra-O-acetyl-α-D-galactopyranosyl Chloride (cas# 14227-87-3) is a compound useful in organic synthesis.

Technology Process of 2,3,4,6-TETRA-O-ACETYL-ALPHA-D-GALACTOPYRANOSYL CHLORIDE

There total 34 articles about 2,3,4,6-TETRA-O-ACETYL-ALPHA-D-GALACTOPYRANOSYL CHLORIDE 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: 97.2%

1,2,3,4,6-penta-O-acetyl-β-D-galactopyranoside → 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl chloride (572-10-1,4451-35-8,4451-36-9,14227-52-2,14227-87-3,14227-88-4,14257-40-0,17081-03-7,19186-60-8,57237-01-1,65982-17-4,65982-18-5,65982-19-6,66966-08-3,144299-57-0)

Guidance literature:

With phosphorus pentachloride; boron trifluoride diethyl etherate; In dichloromethane; for 0.5h;

Reference yield: 94.0%

β-D-galactose peracetate (4163-60-4) → 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl chloride (572-10-1,4451-35-8,4451-36-9,14227-52-2,14227-87-3,14227-88-4,14257-40-0,17081-03-7,19186-60-8,57237-01-1,65982-17-4,65982-18-5,65982-19-6,66966-08-3,144299-57-0)

Guidance literature:

With phosphorus pentachloride; boron trifluoride diethyl etherate; In dichloromethane; for 0.0833333h;

DOI:10.1016/S0040-4039(02)02446-2

Reference yield: 92.0%

2,3,4,6-tetra-O-acetyl-D-mannopyranose (3947-62-4,6207-76-7,10343-06-3,19235-21-3,22554-70-7,22860-22-6,47339-09-3,57884-82-9,62057-79-8,70191-05-8,109525-54-4,140147-37-1) → 2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl chloride (572-10-1,4451-35-8,4451-36-9,14227-52-2,14227-87-3,14227-88-4,14257-40-0,17081-03-7,19186-60-8,57237-01-1,65982-17-4,65982-18-5,65982-19-6,66966-08-3,144299-57-0)

Guidance literature:

With 1,3,5-trichloro-2,4,6-triazine; 1,8-diazabicyclo[5.4.0]undec-7-ene; N,N-dimethyl-formamide; In 1,2-dichloro-ethane; at 60 ℃; for 2h;

DOI:10.1016/j.tetlet.2009.05.077

upstream raw materials:

β-D-mannopyranose pentaacetate

per-O-acetyl-α-D-mannopyranose

2,3,4,6-tetra-O-acetyl-D-mannopyranose

2-(Trimethylsilyl)ethyl-<2,3,4,6-tetra-O-acetyl-α-D-mannopyranosid>

Downstream raw materials:

(1S)-1-(4-methoxy-phenyl)-1,5-anhydro-D-mannitol

2,3,4,6-tetra-O-acetyl-D-mannopyranose

2,3,4,6-tetra-O-acetyl-α/β-D-galactopyranose

1,3,4,6-tetra-O-acetyl-α-D-galactopyranoside

Refernces

• 1、 Li, Zhihao,Bavaro, Teodora,Tengattini, Sara,Bernardini, Roberta,Mattei, Maurizio,Annunziata, Francesca,Cole, Richard B.,Zheng, Changping,Sollogoub, Matthieu,Tamborini, Lucia,Terreni, Marco,Zhang, Yongmin. "Chemoenzymatic synthesis of arabinomannan (AM) glycoconjugates as potential vaccines for tuberculosis". supporting information. . Retrieved 2020/07/27.
• 2、 Pongener, Imlirenla,Nikitin, Kirill,McGarrigle, Eoghan M.. "Synthesis of glycosyl chlorides using catalytic Appel conditions". supporting information. p. 7531 - 7535. Retrieved 2019/08/20.