1,3,4,6-Tetra-O-acetyl-a-D-glucosamineHCI

1,3,4,6-Tetra-O-acetyl-a-D-glucosamineHCI Property

Melting point:

197-200°C

RTECS 

LZ6574000

storage temp. 

Inert atmosphere,2-8°C

solubility 

Methanol (Slightly), Water (Slightly)

form 

Powder

color 

White to Pale Brown

optical activity

[α]/D 30.0±2.0°, c = 1 in H2O

Water Solubility 

Soluble in water at 10mg/ml

InChI

InChI=1/C14H21NO9.ClH/c1-6(16)20-5-10-12(21-7(2)17)13(22-8(3)18)11(15)14(24-10)23-9(4)19;/h10-14H,5,15H2,1-4H3;1H/t10-,11-,12-,13-,14-;/s3

InChIKey

BQLUYAHMYOLHBX-GOLNYAHLNA-N

SMILES

[C@@H]1(OC(=O)C)[C@@H](COC(=O)C)O[C@@H](OC(=O)C)[C@H](N)[C@H]1OC(=O)C.Cl |&1:0,5,12,17,19,r|

Safety

WGK Germany 

3

HS Code 

29329990

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P280Wear protective gloves/protective clothing/eye protection/face protection.

1,3,4,6-Tetra-O-acetyl-a-D-glucosamineHCI Chemical Properties,Usage,Production

Chemical Properties

White Solid

Uses

A potential metabolic inhibitor of cellular-membrane glycoconjugates.

Synthesis

Triester of (2S,3R,4R,5S,6R)-6-(acetyloxymethyl)-3-(((E)-4-methoxybenzylidene)amino)tetrahydro-2H-pyran-2,4,5-triacetate (4.0 g, 8.6 mmol) was used as a raw material and dissolved in preheated acetone (36 mL). Subsequently, 5 M HCl (2 mL) was slowly added to the solution and precipitation was observed. After cooling the reaction mixture to room temperature, ether (36 mL) was added and stirred continuously for 2 hours. The precipitate was collected by filtration, washed with ether and dried under reduced pressure to afford 1,3,4,6-tetra-O-acetyl-2-amino-2-deoxy-D-glucopyranose hydrochloride (2.9 g, 79%) as a white solid. The melting point of the product is 205°C (literature value: 231-233°C, ignition [49], melting point 235°C); specific optical rotation [α] 20D +36.6 (c 1.0, MeOH), literature value [49] +32 (H2O); infrared (IR) spectra (νmax 2939 cm?1 (broad peak, NH3Cl), 1751 cm?1 (C=O); 1H-NMR (DMSO-d6, 300 MHz) δ 1.95 (6H, s, CH3CO), 2.00 (3H, s, CH3CO), 2.14 (3H, s, CH3CO), 3.52 (1H, t, J = 9.7 Hz, H-2), 3.98 (2H, m, H-6, H-5), 4.15 (1H, dd, J = 12.3, 4.1 Hz, H-6), 4.87 (1H, t, J = 9.8 Hz, H-4), 5.28 (1H, t, J = 9.8 Hz, H-3), 5.84 (1H, d, J = 8.8 Hz, H-1), 8.26 (3H, s, NH3Cl).

References

[1] Journal of Organic Chemistry, 1999, vol. 64, # 16, p. 5926 - 5929
[2] Journal of the American Chemical Society, 2018, vol. 140, # 8, p. 3120 - 3127
[3] Carbohydrate Research, 2010, vol. 345, # 11, p. 1541 - 1547
[4] Advanced Synthesis and Catalysis, 2010, vol. 352, # 14-15, p. 2657 - 2662
[5] RSC Advances, 2014, vol. 4, # 12, p. 6239 - 6245