1-O,3-O,4-O,6-O-Tetraacetyl-2-(acetylamino)-2-deoxy-α-D-galactopyranose

Base Information

• Chemical Name: 1-O,3-O,4-O,6-O-Tetraacetyl-2-(acetylamino)-2-deoxy-α-D-galactopyranose
• CAS No.: 10385-50-9
• Molecular Formula: C16H23 N O10
• Molecular Weight: 389.359
• Mol file: 10385-50-9.mol

Synonyms:Galactopyranose,2-acetamido-2-deoxy-, 1,3,4,6-tetraacetate, a-D- (8CI); NSC 231915

Chemical Property of 1-O,3-O,4-O,6-O-Tetraacetyl-2-(acetylamino)-2-deoxy-α-D-galactopyranose

Chemical Property:

• PSA: 143.53000
• LogP: -0.40350

Purity/Quality:

98%,99%, ^*data from raw suppliers

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

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 1-O,3-O,4-O,6-O-Tetraacetyl-2-(acetylamino)-2-deoxy-α-D-galactopyranose

There total 147 articles about 1-O,3-O,4-O,6-O-Tetraacetyl-2-(acetylamino)-2-deoxy-α-D-galactopyranose 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

p-nitrophenyl 2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-β-D-glucopyranoside

Refernces

• 1、 Anders, Thorsten,Adamiak, Kathrin,Keul, Helmut,Elling, Lothar,Moeller, Martin. "Synthesis of a Difunctional Orthogonal Coupler for the Preparation of Carbohydrate-Functionalized sP(EO-stat-PO) Hydrogels". . p. 1201 - 1210. Retrieved 2011.
• 2、 Whitaker et al.. "-". . p. 1885,1888. Retrieved 1962.
• 3、 Chaplin, David,Crout, David H. G.,Bornemann, Stephen,Hutchinson, David W.,Khan, Riaz. "Conversion of 2-Acetamido-2-deoxy-β-D-glucopyranose (N-Acetylglucosamine) into 2-Acetamido-2-deoxy-β-D-galactopyranose (N-Acetylgalactosamine) Using a Biotransformation to Generate a Selectively Deprotected Substrate for SN2 Inversion". . p. 235 - 238. Retrieved 1992.
• 4、 Xiong, Xingquan,Yi, Chao,Han, Qian,Shi, Lin,Li, Sizhong. "I2/ionic liquid as a highly efficient catalyst for per-O-acetylation of sugar under microwave irradiation". . p. 237 - 243. Retrieved 2015.
• 5、 Bhatt, Beenu,Boehm, Raphael,Dyason, Jeffrey C.,Thomson, Robin J.,Von Itzstein, Mark,Kerry, Philip S.,Russell, Rupert J. M.. "Exploring the interactions of unsaturated glucuronides with influenza virus sialidase". . p. 8963 - 8968,6. Retrieved 2012.
• 6、 Traar, Pedro,Belaj, Ferdinand,Francesconi, Kevin A.. "Synthesis of methyl 2-acetamido-2-deoxy-1-seleno-β-D-gluco- And galacto-pyranoside: Selenium metabolites in human urine". . p. 1051 - 1053. Retrieved 2004.
• 7、 Mikeska, Thomas,Nieger, Martin,Mansikkamaeki, Heidi,Daniels, Joerg,Kolter, Thomas. "Crystal structures of O-acetylated 2-acylamino-2-deoxy-D-galactose derivatives". . p. 2119 - 2128. Retrieved 2003.
• 8、 Cao, Zhiling,Qu, Yingying,Zhou, Jiexing,Liu, Weiwei,Yao, Guowei. "Stereoselective Synthesis of Quercetin 3-O-Glycosides of 2-Amino-2-Deoxy-d-Glucose under Phase Transfer Catalytic Conditions". . p. 28 - 40. Retrieved 2015.
• 9、 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.
• 10、 -. "S-ANTIGEN TRANSPORT INHIBITING OLIGONUCLEOTIDE POLYMERS AND METHODS". Paragraph 0068; 0467. . Retrieved 2021/06/22.