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Volumn 3, Issue 1, 2006, Pages 35-38

A facile route for the regioselective deacetylation of peracetylated carbohydrates at anomeric position

Author keywords

Acylation; Carbohydrates; Glycosides; Glycosylations; Regioselectivity

Indexed keywords

EID: 34247181277 PISSN: 15701786 EISSN: None Source Type: Journal
DOI: 10.2174/157017806774964521 Document Type: Article

Times cited : (30)

References (27)

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- Typical Experimental Procedure: Ammonium acetate (0.3 g, 4.0 mmol) was added into a stirred solution of α-D-mannopyranose peracetate 1c (0.8 g, 2.0 mmol) in anhydrous DMF (3 mL, The resulting mixture was stirred at ambient temperature overnight. The solvent was removed under reduced pressure and the residue was purified by flash chromatography (hexane/ethyl acetate) to afford the desired 2,3,4,6-tetra-O-acetyl-D-mannopyranose 2c: 0.7 g (98, All the products except 2h are known compounds. Spectral and analytical data for 2a: [16] 1H NMR (CDCl3, 5.44 (t, 1H, J, 10.2 Hz, 5.36 (bs, 1H, 4.99 (t, 1H, J= 10.2 Hz, 4.78 (dd, 1H, J, 3.5, 3.5 Hz, 4.19, 4.13 (m, 2H, 4.01 (d, 1H, J, 5.6 Hz, 2.00 (s, 3H, 1.99 (s, 3H, 1.98 (s, 3H, 1.95 (s. 3H, 13C NMR CDCl3, δ, 171.24, 170.54, 170.52, 169.99, 90.11, 71.37, 70.12, 68.70, 67.10, 62.19, 20.88, 20.85, 20.77, 20.77. C
- 3): δ = 170.92, 170.84, 170.64, 170.53, 169.96, 169.56, 169.30, 100.97, 100.96, 95.35, 90.15, 73.42, 73.19, 73.11, 72.22, 72.06, 71.83, 71.52, 69.55, 68.29, 68.00, 62.00, 61.77, 20.94, 20.85, 20.74.

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