ChemicalBook CAS DataBase List N-ACETYL-ALPHA-D-GLUCOSAMINE

N-ACETYL-ALPHA-D-GLUCOSAMINE synthesis

8synthesis methods

Product Name:N-ACETYL-ALPHA-D-GLUCOSAMINE
CAS Number:10036-64-3
Molecular formula:C8H15NO6
Molecular Weight:221.21

(3R,4R,5S,6R)-3-amino-6-(hydroxymethyl)tetrahydro-2H-pyran-2,4,5-triol hydrochloride

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75-36-5 Synthesis

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Yield:-

Reaction Conditions:

Stage #1: (+)-D-glucosamine hydrochloridewith triethylamine in methanol at 20; for 0.5 h;
Stage #2: acetyl chloride in methanol;diethyl ether; for 2.5 h;Cooling with ice;Overall yield = 63 percent;

Steps:

Synthesis of N-acyl-D-glucosamines (2)

General procedure: Glucosamine hydrochloride (11.6 mmol) was suspended in methanol(30 mL) containing triethylamine (34.8 mmol). The mixture was vigorouslystirred at room temperature for 0.5 h, and then cooled to 5 C before theprecipitates of triethylamine hydrochloride were filtered off. Acyl chloride(15.0 mmol) was slowly added dropwise into the filtrate over 0.5 h, anddiethyl ether (50 mL) was then added. The mixture was vigorously stirredin an ice bath to rapidly precipitate. After chilling for 2 h, the solid materialwas filtered, washed with ether and dichloromethane, and dried to giveproducts 2a-2h.

References:

Cao, Zhi-ling;Zhu, Cong;Wu, Wen-ying;Zhu, Dan-dan;Qian, Dong;Zhu, Jian;Chang, Tian-ge;Sheng, Mei;Yang, Xiu-li;Liu, Wei-wei [Journal of Carbohydrate Chemistry,2020,vol. 39,# 9,p. 472 - 484]