BENZYL 2-ACETAMIDO-2-DEOXY-ALPHA-D-GLUCOPYRANOSIDE Chemical Properties

Melting point:

183-185°C

Boiling point:

594.9±50.0 °C(Predicted)

Density 

1.34±0.1 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Store in freezer, under -20°C

solubility 

DMSO (Slightly), Methanol (Slightly), Water (Slightly)

form 

Solid

pka

12.98±0.70(Predicted)

color 

White

optical activity

Consistent with structure

CAS DataBase Reference

13343-62-9(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Hazard Note 

Irritant

HS Code 

29389090

BENZYL 2-ACETAMIDO-2-DEOXY-ALPHA-D-GLUCOPYRANOSIDE Usage And Synthesis

Chemical Properties

White Powder

Uses

Phenylmethyl 2-(acetylamino)-2-deoxy-α-D-glucopyranoside is a class of biochemical reagents used in glycobiology research. Glycobiology studies the structure, synthesis, biology, and evolution of sugars. It involves carbohydrate chemistry, enzymology of glycan formation and degradation, protein-glycan recognition, and the role of glycans in biological systems. This field is closely related to basic research, biomedicine, and biotechnology[1].

Synthesis

GENERAL STEPS: N-acetylglucosamine (6.40 g, 28.9 mmol) was dissolved in benzyl alcohol (50 mL, 480 mmol) and concentrated aqueous hydrochloric acid solution (3.0 mL) was added. The reaction mixture was stirred at 90°C for 3 hours. After completion of the reaction, the crude product was cooled to room temperature, poured into ether (500 mL) and crystallized at 4°C for 18 hours. The crystallized product was collected by filtration and washed with petroleum ether. Purification by silica gel column chromatography (eluent: dichloromethane/methanol, 95:5 to 88:12, v/v) afforded benzylglycoside 2 (6.67 g, 21.4 mmol, 74% yield) as a white, foamy solid. rf = 0.25 (dichloromethane/methanol, 90:10, v/v); melting point 182-184°C; [α]D17.8 = +222 (c 0.1, methanol); IR (thin film) νmax 3298, 3092, 2938, 2901, 2844, 1648, 1552, 1497, 1455, 1375, 1309, 1230, 1156, 1093, 1047, 778, 732, 695 cm?1; 1H NMR (500 MHz, CD3OD) δ 7.40-7.25 (m, 5H, aromatic H), 4.85 (d, 1H, J = 3.6 Hz, H-1′), 4.74 (d, 1H, J = 12.0 Hz, H-1a), 4.49 (d, 1H, J = 12.0 Hz, H-1b), 3.89 (dd, 1H, J = 3.6, 10.8 Hz, H-2′), 3.83 ( dd, 1H, J = 1.6, 11.4 Hz, H-6a′), 3.73-3.64 (m, 3H, H-6b′, H-3′, H-4′), 3.36 (dd, 1H, J = 9.6 Hz, H-5′), 1.95 (s, 3H, acetyl CH3); 13C NMR (125 MHz, CD3OD) δ 173.6 (C= O, acetyl), 139.0 (aromatic quaternary carbon), 129.4, 129.3, 128.8 (aromatic CH), 97.5 (C-1′), 74.1 (C-4′), 72.7 (C-3′), 72.5 (C-5′), 70.1 (C-1), 62.7 (C-6′), 55.4 (C-2′), 22.5 (acetyl CH3 ); HRMS (ESI) m/z [C15H22NO6]+ Calculated value: 312.1442, measured value: 312.1446.

References

[1] Varki A, et al editors. Essentials of Glycobiology [Internet]. 4th ed. Cold Spring Harbor (NY): Cold Spring Harbor Laboratory Press; 2022. PMID:35536922

BENZYL 2-ACETAMIDO-2-DEOXY-ALPHA-D-GLUCOPYRANOSIDE(13343-62-9)Related Product Information

• BENZYL 2-ACETAMIDO-2-DEOXY-ALPHA-D-GLUCOPYRANOSIDE
• 2-[[7-(ACETYLAMINO)-6-(BENZYLOXY)-2-PHENYLPERHYDROPYRANO[3,2-D][1,3]DIOXIN-8-YL]OXY]PROPANOIC ACID
• BENZYL 2-ACETAMIDO-2-DEOXY-3-O-(2,3,4,6-TETRA-O-ACETYL-BETA-D-GALACTOPYRANOSYL)-A-D-GLUCOPYRANOSIDE
• 1-Benzyl 2-Acetamido-6-O-benzyl-4-(2,3,4,6-tetra-O-acetyl-b-D-galactopyranosyl)-2-deoxy-a-D-glucopyranoside
• AC-ALPHA-BENZYL-4,6-O-BENZYLIDENE-MURAMIC ACID
• Benzyl2-acetamido-4,6-O-benzylidene-3-O-(carboxymethyl)-2-deoxy-a-D-glucopyranoside
• BENZYL 2-ACETAMIDO-2-DEOXY-3,6-DI-O-ACETYL-ALPHA-D-GLUCOPYRANOSIDE
• BENZYL N-ACETYL-4,6-O-BENZYLIDENE-A-D-MURAMIC ACID, METHYL ESTER
• BENZYL 2-ACETAMIDO-3,6-DI-O-BENZYL-2-DEOXY-ALPHA-D-GLUCOPYRANOSIDE
• BENZYL 2-ACETAMIDO-3-O-ALLYL-4,6-O-BENZYLIDENE-2-DEOXY-ALPHA-D-GLUCOPYRANOSIDE
• BENZYL 2-ACETAMIDO-2-DEOXY-6-O-TRIPHENYL-METHYL-ALPHA-D-GLUCOPYRANOSIDE
• BENZYL 2-ACETAMIDO-2-DEOXY-3-O-METHYL-ALPHA-D-GLUCOPYRANOSIDE
• BENZYL 2-ACETAMIDO-4,6-O-BENZYLIDENE-3-O-(2,3,4,6-TETRA-O-ACETYL-BETA-D-GALACTOPYRANOSYL)-2-DEOXY-ALPHA-D-GLUCOPYRANOSIDE
• Benzyl 2-Acetamido-2-deoxy-4-O-b-D-galactofuranosyl-a-D-glucopyranoside
• Benzyl 2-Acetamido-2-deoxy-4,6-O-isopropylidene-a-D-glucopyranoside
• Benzyl 2-Acetamido-2-deoxy-3-O-(b-D-galactopyranosyl)-a-D-glucopyranoside
• BENZYL N-ACETYL-6-O-BENZYL-A-D-MURAMIC ACID, METHYL ESTER
• BENZYL 2-ACETAMIDO-4,6-O-BENZYLIDENE-2-DEOXY-ALPHA-D-GLUCOPYRANOSIDE