METHYL 2-ACETAMIDO-2-DEOXY-BETA-D-GLUCOPYRANOSIDE

Base Information

• Chemical Name: METHYL 2-ACETAMIDO-2-DEOXY-BETA-D-GLUCOPYRANOSIDE
• CAS No.: 3946-01-8
• Molecular Formula: C9H17 N O6
• Molecular Weight: 235.237
• Mol file: 3946-01-8.mol

Synonyms:Glucopyranoside,methyl 2-acetamido-2-deoxy-, b-D- (8CI); Methyl 2-acetamido-2-deoxy-b-D-glucopyranoside; Methyl 2-acetamido-2-deoxy-b-D-glucoside; Methyl2-deoxy-2-acetamido-b-D-glucopyranoside; Methyl N-acetyl-b-D-glucosaminide; Methyl N-acetylglucosaminide; b-Methyl N-acetyl-D-glucosamine; b-Methyl N-acetylglucosaminide

Chemical Property of METHYL 2-ACETAMIDO-2-DEOXY-BETA-D-GLUCOPYRANOSIDE

Chemical Property:

• Melting Point: 204-206°C
• PSA: 108.25000
• Density: 1.36
• LogP: -2.03260
• Storage Temp.: 2-8°C
• Solubility.: Methanol (Slightly), Water (Slightly)

Purity/Quality:

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

Methyl 2-acetamido-2-deoxy-b-D-glucopyranoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: Methyl 2-Acetamido-2-deoxy-β-D-glucopyranoside (cas# 3946-01-8) is a compound useful in organic synthesis.

Technology Process of METHYL 2-ACETAMIDO-2-DEOXY-BETA-D-GLUCOPYRANOSIDE

There total 55 articles about METHYL 2-ACETAMIDO-2-DEOXY-BETA-D-GLUCOPYRANOSIDE 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: 100.0%

methanol (67-56-1) + N-Acetyl-D-glucosamine (7512-17-6,72-87-7,1136-42-1,1136-44-3,6082-29-7,6730-06-9,7772-94-3,10036-64-3,14131-60-3,14131-64-7,14131-68-1,14215-68-0,62057-49-2,62057-50-5,62057-51-6,62057-52-7,62057-53-8,62057-54-9,62057-55-0,62057-56-1,62075-50-7,62137-54-6,134451-97-1,134522-12-6,148347-16-4) → methyl N-acetyl-D-glucosamine (3055-46-7,3946-01-8,5627-24-7,6082-04-8,6082-22-0,17327-09-2,22256-76-4,32087-35-7,32087-36-8,95341-97-2,114029-61-7,114612-10-1,114612-13-4,116559-74-1)

Guidance literature:

With acetyl chloride; for 23h;

DOI:10.1039/b309715n

Reference yield: 100.0%

methyl 2-acetamido-3,4,6-O-triacetyl-2-deoxy-β-D-glucopyranoside (2771-48-4) → methyl N-acetyl-β-D-glucosaminide (3946-01-8)

Guidance literature:

With sodium methylate; In methanol; at 20 ℃; for 5h; Inert atmosphere; Schlenk technique;

DOI:10.1021/acs.orglett.5b02413

Reference yield: 98.0%

methanol (67-56-1) + 2-methyl-(1,2-dideoxy-5,6-O-isopropylidene-α-D-glucofurano)-<2,1-d>-2-oxazoline (117177-19-2) → methyl N-acetyl-β-D-glucosaminide (3946-01-8)

Guidance literature:

With toluene-4-sulfonic acid; at 20 ℃; for 5h;

DOI:10.1021/ol051523k

upstream raw materials:

diazomethane

methanol

diethyl ether

2-acetamido-2-deoxy-D-glucose

Downstream raw materials:

N-((4aR,6S,7R,8R,8aS)-8-Hydroxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-acetamide

methyl-[2-(2,4-dinitro-anilino)-2-deoxy-β-D-glucopyranoside]

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

methyl 2-acetamido-3,4-di-O-acetyl-2-deoxy-6-O-triphenylmethyl-β-D-glucopyranoside

Refernces

• 1、 Sandford et al.. "-". . p. 153,154-164. Retrieved 1973.
• 2、 Malik, Leila,Nygaard, Jesper,Cristensen, Niels J.,Madsen, Charlotte S.,R?sner, Heike I.,Kragelund, Birthe B.,Hoiberg-Nielsen, Rasmus,Streicher, Werner W.,Arleth, Lise,Thulstrup, Peter W.,Jensen, Knud J.. "A de Novo-Designed Monomeric, Compact Three-Helix-Bundle Protein on a Carbohydrate Template". . p. 1905 - 1918. Retrieved 2015.
• 3、 Chen, Anji,Adhikari, Surya B.,Mays, Kellie,Wang, Guijun. "Synthesis and Study of Molecular Assemblies Formed by 4,6-O-(2-Phenylethylidene)-Functionalized d -Glucosamine Derivatives". . p. 8076 - 8089. Retrieved 2017.
• 4、 Pettenuzzo, Andrea,Vezzù, Keti,Di Paolo, Maria Luisa,Fotopoulou, Eirini,Marchiò, Luciano,Via, Lisa Dalla,Ronconi, Luca. "Design, physico-chemical characterization andin vitrobiological activity of organogold(iii) glycoconjugates". supporting information. p. 8963 - 8979. Retrieved 2021/07/02.
• 5、 García-Oliva, Cecilia,Cabanillas, Alfredo H.,Perona, Almudena,Hoyos, Pilar,Rumbero, ángel,Hernáiz, María J.. "Efficient Synthesis of Muramic and Glucuronic Acid Glycodendrimers as Dengue Virus Antagonists". supporting information. p. 1588 - 1596. Retrieved 2020/02/05.