1,2,3,4,6-PENTA-O-ACETYL-ALPHA-D-MANNOPYRANOSE Chemical Properties

Melting point:

64-75°C

Boiling point:

135 °C(Press: 0.0001 Torr)

Density 

1.30

storage temp. 

Sealed in dry,Store in freezer, under -20°C

solubility 

Soluble in chloroform

form 

Powder

color 

White to Off-white

InChI

InChI=1/C16H22O11/c1-7(17)22-6-12-13(23-8(2)18)14(24-9(3)19)15(25-10(4)20)16(27-12)26-11(5)21/h12-16H,6H2,1-5H3/t12-,13-,14+,15+,16+/s3

InChIKey

LPTITAGPBXDDGR-OWYFMNJBSA-N

SMILES

[C@@H]1(OC(=O)C)[C@H](OC(=O)C)[C@H](O[C@H](COC(=O)C)[C@H]1OC(=O)C)OC(=O)C |&1:0,5,10,12,18,r|

CAS DataBase Reference

4163-65-9(CAS DataBase Reference)

Safety Information

WGK Germany 

3

MSDS

• Language:English Provider:SigmaAldrich

1,2,3,4,6-PENTA-O-ACETYL-ALPHA-D-MANNOPYRANOSE Usage And Synthesis

Uses

1,2,3,4,6-Penta-O-acetyl-α-D-mannopyranose (cas# 4163-65-9) is a compound useful in organic synthesis.

Uses

1,2,3,4,6-PENTA-O-ACETYL-ALPHA-D-MANNOPYRANOSE was used for glycosylation in a study that assessed novel synthetic inhibitors of selectin-mediated cell adhesion. 1 It has also been used in a study to investigate stereospecific entry to spiroketal glycosides using alkylidenecarbene CH insertion.

Synthesis

D-Anhydrous glucose (3.00 g, 16.6 mmol) was dissolved in anhydrous pyridine (33 mL) and acetic anhydride (31.5 mL, 333 mmol) was added slowly and dropwise at 0 °C and under nitrogen protection. The reaction mixture was stirred at 0 °C for 1 h. After that, a catalytic amount of DMAP (200 mg, 1.67 mmol) was added. Subsequently, the reaction mixture was gradually warmed up to room temperature, during which a slight exothermic phenomenon was observed. After 6 hours of reaction, the clarified yellow reaction solution was slowly poured into rapidly stirred ice water (125 mL) and a viscous solid was precipitated. After extraction by ethyl acetate (345 mL), the solvent was evaporated and co-evaporated with anhydrous toluene (320 mL) to give the final fully acetylated glucose as a yellow solid (5.84 g, 90% yield).

References

[1] Angewandte Chemie, International Edition, 2009, vol. 48, p. 2723 - 2726
[2] Angewandte Chemie, 2009, vol. 121, p. 2761 - 2764
[3] Tetrahedron, 2013, vol. 69, # 41, p. 8731 - 8737
[4] Green Chemistry, 2011, vol. 13, # 1, p. 59 - 63
[5] Journal of the Chinese Chemical Society, 2009, vol. 56, # 2, p. 398 - 403

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