D-Galactosamine pentaacetate

Base Information

• Chemical Name: D-Galactosamine pentaacetate
• CAS No.: 76375-60-5
• Molecular Formula: C16H23NO10
• Molecular Weight: 389.359
• Hs Code.: 29400090
• Mol file: 76375-60-5.mol

Synonyms:Galactopyranose,2-acetamido-2-deoxy-, tetraacetate (7CI);2-Acetamido-1,3,4,6-tetra-O-acetyl-2-deoxy-D-galactopyranose;

Chemical Property of D-Galactosamine pentaacetate

Chemical Property:

• Appearance/Colour: White
• Melting Point: 230 °C (dec.)
• Boiling Point: 530.163 °C at 760 mmHg
• PKA: 13.41±0.70(Predicted)
• Flash Point: 274.433 °C
• PSA: 143.53000
• Density: 1.3 g/cm³
• LogP: -0.40350
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly, Sonicated), DMSO (Slightly)

Purity/Quality:

98% ^*data from raw suppliers

2-Acetamido-1,3,4,6-tetra-O-acetyl-2-deoxy-D-galactopyranose ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Anti-tumour agent.

Technology Process of D-Galactosamine pentaacetate

There total 124 articles about D-Galactosamine pentaacetate 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: 95.0%

2-amino-2-deoxy-D-glucose hydrochloride + acetic anhydride (108-24-7) → 2-acetamido-1,3,4,6-tetra-O-acetyl-2-deoxy-β-D-glucopyranose (3006-60-8,4539-83-7,6730-10-5,7772-79-4,7784-54-5,10385-50-9,14086-90-9,26151-16-6,76375-60-5,76375-61-6,95341-98-3,95341-99-4,134451-91-5,134451-96-0,136982-81-5,145375-11-7,148347-15-3)

Guidance literature:

With pyridine; at 20 ℃; Cooling with ice;

DOI:10.1080/07328303.2014.996290

Reference yield: 90.0%

1,3,4,6-tetra-O-acetyl-D-glucosamine hydrochloride (5432-46-2,10034-19-2,10034-20-5,34948-62-4,110253-00-4,1191127-63-5) + acetic anhydride (108-24-7) → 2-acetamido-1,3,4,6-tetra-O-acetyl-2-deoxy-β-D-glucopyranose (3006-60-8,4539-83-7,6730-10-5,7772-79-4,7784-54-5,10385-50-9,14086-90-9,26151-16-6,76375-60-5,76375-61-6,95341-98-3,95341-99-4,134451-91-5,134451-96-0,136982-81-5,145375-11-7,148347-15-3)

Guidance literature:

With pyridine;

DOI:10.1002/ejoc.201200062

Reference yield: 88.0%

N-acetyl-D-glucosamine (14131-68-1) + acetic anhydride (108-24-7) → 2-acetamido-1,3,4,6-tetra-O-acetyl-2-deoxy-β-D-glucopyranose (3006-60-8,4539-83-7,6730-10-5,7772-79-4,7784-54-5,10385-50-9,14086-90-9,26151-16-6,76375-60-5,76375-61-6,95341-98-3,95341-99-4,134451-91-5,134451-96-0,136982-81-5,145375-11-7,148347-15-3)

Guidance literature:

With pyridine; at 20 ℃; for 29.5h;

upstream raw materials:

acetic anhydride

2-amino-2-deoxy-D-idose; hydrochloride

1,3,4,6-tetra-O-acetyl-D-glucosamine hydrochloride

D-(+)-glucosamine hydrochloride

Downstream raw materials:

[1]naphthyl-(tri-O-acetyl-2-acetylamino-2-deoxy-β-D-glucopyranoside)

2-acetylamino-1,1-diphenyl-1,2-dideoxy-D-glucitol

methyl 2-acetamido-2-deoxy-3,4,6-tri-O-methyl-β-D-glucopyranoside

1-(2-naphthyl) 3,4,6-tri-O-acetyl-2-acetamido-2-deoxy-β-D-glucopyranoside

Refernces

• 1、 Yan, Bingjia,Li, Wenyi,Hackenberger, Christian P. R.. "A silyl ether-protected building block forO-GlcNAcylated peptide synthesis to enable one-pot acidic deprotection". supporting information. p. 8014 - 8017. Retrieved 2021/10/04.
• 2、 Morelli, Laura,Legnani, Laura,Ronchi, Silvia,Confalonieri, Laura,Imperio, Daniela,Toma, Lucio,Compostella, Federica. "2,3-Carbamate mannosamine glycosyl donors in glycosylation reactions of diacetone-D-glucose. An experimental and theoretical study". . . Retrieved 2021/08/26.