1,3,4,6-Tetra-O-acetyl-β-D-mannopyranose Chemical Properties

Melting point:

160-161 °C(lit.)

Boiling point:

425.5±45.0 °C(Predicted)

Density 

1.33±0.1 g/cm3(Predicted)

refractive index 

-22.5 ° (C=1.4, CHCl3)

storage temp. 

Sealed in dry,2-8°C

solubility 

very faint turbidity in Chloroform

form 

powder to crystal

pka

12.22±0.70(Predicted)

color 

White to Almost white

optical activity

[α]19/D 68°, c = 0.7 in pyridine

BRN 

96634

InChI

InChI=1/C14H20O10/c1-6(15)20-5-10-12(21-7(2)16)13(22-8(3)17)11(19)14(24-10)23-9(4)18/h10-14,19H,5H2,1-4H3/t10-,11+,12-,13-,14-/s3

InChIKey

SHBHJRVMGYVXKK-XVIXHAIJSA-N

SMILES

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

CAS DataBase Reference

18968-05-3(CAS DataBase Reference)

Safety Information

Safety Statements 

22-24/25

WGK Germany 

3

HS Code 

29400090

MSDS

• Language:English Provider:SigmaAldrich

1,3,4,6-Tetra-O-acetyl-β-D-mannopyranose Usage And Synthesis

Uses

1,3,4,6-Tetra-o-acetyl-beta-d-mannopyranose is an intermediate in the preparation of precursors of 2-[18F]fluoro-2-deoxy-D-glucose for diagnostic use in positron emission tomography.

Synthesis

General procedure for the synthesis of (2S,3S,4R,5R,6R)-6-(acetyloxymethyl)-3-hydroxytetrahydro-2H-pyran-2,4,5-triyl triacetate from 1,2-O-(1-ethoxyethylidene)-β-D-mannopyranose triacetate: to a solution of anhydrous acetone (27 mL) of the protoacid ester (4.4 g, 12 mmol), a slow addition of a 1 M aqueous hydrochloric acid (HCl) solution (2.7 mL), and the reaction was carried out under vigorous stirring (the water bath temperature was maintained at about 18 °C). The reaction mixture was continued to be stirred at room temperature for 5 min before being concentrated on a rotary evaporator, keeping the temperature below 20 °C. The concentrated solid was dissolved in chloroform (CHCl3, 25 mL) and washed with deionized water (2 x 10 mL). The organic phase was dried over anhydrous sodium sulfate (Na2SO4) and filtered, and the filtrate was concentrated on a rotary evaporator. The residue was ground with ether (Et2O) and recrystallized from ethanol (EtOH) to give the target product tetraacetylmannose (1.9 g, 45% yield) as a white solid. Thin layer chromatography (TLC) Rf value was 0.13 (unfolding agent: hexane/ethyl acetate = 1:1). The melting point is 134-136°C. High Resolution Mass Spectrometry (HRMS-ESI): m/z C14H20NaO10 ([M+Na]+) Calculated value 371.09542, measured value 371.09581 (error 0.39 mmu, 1.06 ppm).

References

[1] Bioorganic and Medicinal Chemistry, 2018, vol. 26, # 8, p. 1848 - 1858
[2] Tetrahedron, 1992, vol. 48, # 47, p. 10249 - 10264
[3] Tetrahedron Letters, 2013, vol. 54, # 17, p. 2190 - 2193

1,3,4,6-Tetra-O-acetyl-β-D-mannopyranose(18968-05-3)Related Product Information

• 1,3-BUTANEDIOL DIACETATE
• 1,1,3-TRIETHOXYPROPANE
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• 1,3-Diacetoxy-2-(acetoxymethoxy)propane
• 1,4-DIACETOXYBUTANE
• Diacetin
• 2-[(Acetyloxy)methoxy]ethyl acetate
• D-Mannitol
• D-LYXOSE
• L(+)-Rhamnose monohydrate
• 1,6-Diacetoxyhexane
• 2-Butoxyethyl acetate
• 1,1,3-TRIMETHOXYBUTANE
• TATM
• D-Mannose
• (R)-1,2-4-TRIACETOXYBUTANE
• BETA-METHYL-D-LYXOPYRANOSIDE
• 1,3,4,6-Tetra-O-acetyl-β-D-mannopyranose