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Volumn 2, Issue 3, 2005, Pages 242-246

Sc(OTf)3 efficiently catalyzed the glycosidation of 1-C-alkyl-2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl acetates with alcohols

Author keywords

1 C alkyl glycoside; Glycosidation; Glycosyl acetate; Ketoside; Lewis acid; Sc(OTf)3

Indexed keywords

EID: 28844505561 PISSN: 15701786 EISSN: None Source Type: Journal
DOI: 10.2174/1570178053765410 Document Type: Review

Times cited : (17)

References (19)

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- Chemical glycosidation; a) Li, X. L.; Ohtake, H.; Takahashi, H.; Ikegami, S. Tetrahedron, 2001, 57, 4283;

3
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5
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- Enzymatic glycosidation;
- d) Chang, C-F.; Yang, W-B.; Chang, C-C.; Lin, C-H. Tetrahedron Lett., 2002, 43, 6515; Enzymatic glycosidation;
- (2002) Tetrahedron Lett , vol.43 , pp. 6515
- Chang, C.-F.¹ Yang, W.-B.² Chang, C.-C.³ Lin, C.-H.⁴

6
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9
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- Li, X.L.¹ Ohtake, H.² Takahashi, H.³ Ikegami, S.⁴

10
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- As the analogs of the 1-C-alkyl-hexopyranose derivatives, the glycosidation using the 1-C-alkoxyalkyl-hexopyranose derivatives was reported; Heskamp, B. M.; Veeneman, G. H.; van der Marel, G. A.; van Boeckel, C. A. A.; van Boom, J. H. Tetrahedron, 1995, 51, 5657.
- b) As the analogs of the 1-C-alkyl-hexopyranose derivatives, the glycosidation using the 1-C-alkoxyalkyl-hexopyranose derivatives was reported; Heskamp, B. M.; Veeneman, G. H.; van der Marel, G. A.; van Boeckel, C. A. A.; van Boom, J. H. Tetrahedron, 1995, 51, 5657.

11
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- As the 1-C-alkyl-hexofuranose derivative, the glycosidation using 2,3:5,6-di-O- isopropylidene-1-C-methyl-D-mannofuranosyl acetate was reported; Dondoni, A.; Marra, A.; Rojo, I.; Scherrmann, M.-C. Tetrahedron, 1996, 52, 3057.
- c) As the 1-C-alkyl-hexofuranose derivative, the glycosidation using 2,3:5,6-di-O- isopropylidene-1-C-methyl-D-mannofuranosyl acetate was reported; Dondoni, A.; Marra, A.; Rojo, I.; Scherrmann, M.-C. Tetrahedron, 1996, 52, 3057.

12
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14
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16
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- 2,3,4,6-Tetra-O-benzyl-1-C-methyl-α-D-glucopyranosyl acetate has also been synthesized from 1 by a multistep reaction sequence; Fukase, H.; Horii, S. J. Org. Chem., 1992, 57, 3642.
- 2,3,4,6-Tetra-O-benzyl-1-C-methyl-α-D-glucopyranosyl acetate has also been synthesized from 1 by a multistep reaction sequence; Fukase, H.; Horii, S. J. Org. Chem., 1992, 57, 3642.

17
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- 2O gave the open ring compound; Heskamp, B. M.; Noort, D.; van der Marel, G. A.; van Boom, J. H. Synlett, 1992, 713.
- 2O gave the open ring compound; Heskamp, B. M.; Noort, D.; van der Marel, G. A.; van Boom, J. H. Synlett, 1992, 713.

18
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19
- 46249125151
- A typical glycosidation procedure is as follows: To a stirred solution of Sc(OTf)3 (4.4 mg, 0.0089 mmol) and phenethyl alcohol (20.7 mg, 0.17 mmol) in toluene was added 3a (101.2 mg, 0.17 mmol) at 0 °C. The resulting mixture was stiffed for 1 h. The reaction was then quenched by the addition of a sat. NaHCO3 solution (5 mL, The reaction mixture was extracted with CHCl3, and the organic layer was washed with water and a sat. NaCl solution. After the organic layer was dried over Na2SO4, the solvent was evaporated under reduced pressure. The crude product was purified by preparative silica gel TLC (ethyl acetate/hexane=1/4, to give 4a as a white oil (99.2 mg, 89, 4a: 1H NMR (400 MHz, CDCl3, δ1.26 (3H, s, CH3, 2.93 (2H, m, OCH2C H2Ph, 3.31 (1H, d, J, 9.5 Hz, H-2, 3.36 (1H, m, H-5, 3.52-3.59 (3H, m, H-6 and H-4, 3.61-3.66 2H
- 3)

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