New Synthetic Methodology for Regio- and Stereoselective Synthesis of Oligosaccharides via Sugar Ortho Ester Intermediates

Journal of Organic Chemistry

Volumn 63, Issue 17, 1998, Pages 5744-5745

  Wang, Wei ^a   Kong, Fanzuo ^a  

^a RESEARCH CENTER FOR ECO ENVIRONMENTAL SCIENCES   (China)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001206769     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo981135e     Document Type: Article

References (33)

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5. General reviews: (a) Preparative Carbohydrate Chemistry; Hanessian, S., Ed.; Marcel Dekker Inc.: New York, 1997; Chapters 12-22. (b) Barresi, F.; Hindsgaul, O. J. Carbohydr. Chem. 1995, 14, 1043. (c) Schmidt, R. R.; Kinzy, W. Adv. Carbohydr. Chem. Biochem. 1994, 50, 21. (d) Toshima, K.; Tatsuta, K. Chem. Rev. 1993, 93, 1503. Glycal donors: Dannishefsky, S. J.; Bilodeau, M. T. Angew. Chem., Int. Ed. Engl. 1996, 35, 1380. Glycosyl sulfoxide donors: Yan, L.; Kahne, D. J. Am. Chem. Soc. 1996, 118, 9239. 1-Hydroxy glycosyl donors: Garcia, B. A.; Poole, J. A.; Gin, D. Y. J. Am. Chem. Soc. 1997, 119, 7597. 1,2-Anhyrdo glycosyl donors: Du, Y.; Kong, F. Tetrahedron Lett. 1995, 427.
6. General reviews: (a) Preparative Carbohydrate Chemistry; Hanessian, S., Ed.; Marcel Dekker Inc.: New York, 1997; Chapters 12-22. (b) Barresi, F.; Hindsgaul, O. J. Carbohydr. Chem. 1995, 14, 1043. (c) Schmidt, R. R.; Kinzy, W. Adv. Carbohydr. Chem. Biochem. 1994, 50, 21. (d) Toshima, K.; Tatsuta, K. Chem. Rev. 1993, 93, 1503. Glycal donors: Dannishefsky, S. J.; Bilodeau, M. T. Angew. Chem., Int. Ed. Engl. 1996, 35, 1380. Glycosyl sulfoxide donors: Yan, L.; Kahne, D. J. Am. Chem. Soc. 1996, 118, 9239. 1-Hydroxy glycosyl donors: Garcia, B. A.; Poole, J. A.; Gin, D. Y. J. Am. Chem. Soc. 1997, 119, 7597. 1,2-Anhyrdo glycosyl donors: Du, Y.; Kong, F. Tetrahedron Lett. 1995, 427.
7. General reviews: (a) Preparative Carbohydrate Chemistry; Hanessian, S., Ed.; Marcel Dekker Inc.: New York, 1997; Chapters 12-22. (b) Barresi, F.; Hindsgaul, O. J. Carbohydr. Chem. 1995, 14, 1043. (c) Schmidt, R. R.; Kinzy, W. Adv. Carbohydr. Chem. Biochem. 1994, 50, 21. (d) Toshima, K.; Tatsuta, K. Chem. Rev. 1993, 93, 1503. Glycal donors: Dannishefsky, S. J.; Bilodeau, M. T. Angew. Chem., Int. Ed. Engl. 1996, 35, 1380. Glycosyl sulfoxide donors: Yan, L.; Kahne, D. J. Am. Chem. Soc. 1996, 118, 9239. 1-Hydroxy glycosyl donors: Garcia, B. A.; Poole, J. A.; Gin, D. Y. J. Am. Chem. Soc. 1997, 119, 7597. 1,2-Anhyrdo glycosyl donors: Du, Y.; Kong, F. Tetrahedron Lett. 1995, 427.
8. General reviews: (a) Preparative Carbohydrate Chemistry; Hanessian, S., Ed.; Marcel Dekker Inc.: New York, 1997; Chapters 12-22. (b) Barresi, F.; Hindsgaul, O. J. Carbohydr. Chem. 1995, 14, 1043. (c) Schmidt, R. R.; Kinzy, W. Adv. Carbohydr. Chem. Biochem. 1994, 50, 21. (d) Toshima, K.; Tatsuta, K. Chem. Rev. 1993, 93, 1503. Glycal donors: Dannishefsky, S. J.; Bilodeau, M. T. Angew. Chem., Int. Ed. Engl. 1996, 35, 1380. Glycosyl sulfoxide donors: Yan, L.; Kahne, D. J. Am. Chem. Soc. 1996, 118, 9239. 1-Hydroxy glycosyl donors: Garcia, B. A.; Poole, J. A.; Gin, D. Y. J. Am. Chem. Soc. 1997, 119, 7597. 1,2-Anhyrdo glycosyl donors: Du, Y.; Kong, F. Tetrahedron Lett. 1995, 427.
9. General reviews: (a) Preparative Carbohydrate Chemistry; Hanessian, S., Ed.; Marcel Dekker Inc.: New York, 1997; Chapters 12-22. (b) Barresi, F.; Hindsgaul, O. J. Carbohydr. Chem. 1995, 14, 1043. (c) Schmidt, R. R.; Kinzy, W. Adv. Carbohydr. Chem. Biochem. 1994, 50, 21. (d) Toshima, K.; Tatsuta, K. Chem. Rev. 1993, 93, 1503. Glycal donors: Dannishefsky, S. J.; Bilodeau, M. T. Angew. Chem., Int. Ed. Engl. 1996, 35, 1380. Glycosyl sulfoxide donors: Yan, L.; Kahne, D. J. Am. Chem. Soc. 1996, 118, 9239. 1-Hydroxy glycosyl donors: Garcia, B. A.; Poole, J. A.; Gin, D. Y. J. Am. Chem. Soc. 1997, 119, 7597. 1,2-Anhyrdo glycosyl donors: Du, Y.; Kong, F. Tetrahedron Lett. 1995, 427.
10. General reviews: (a) Preparative Carbohydrate Chemistry; Hanessian, S., Ed.; Marcel Dekker Inc.: New York, 1997; Chapters 12-22. (b) Barresi, F.; Hindsgaul, O. J. Carbohydr. Chem. 1995, 14, 1043. (c) Schmidt, R. R.; Kinzy, W. Adv. Carbohydr. Chem. Biochem. 1994, 50, 21. (d) Toshima, K.; Tatsuta, K. Chem. Rev. 1993, 93, 1503. Glycal donors: Dannishefsky, S. J.; Bilodeau, M. T. Angew. Chem., Int. Ed. Engl. 1996, 35, 1380. Glycosyl sulfoxide donors: Yan, L.; Kahne, D. J. Am. Chem. Soc. 1996, 118, 9239. 1-Hydroxy glycosyl donors: Garcia, B. A.; Poole, J. A.; Gin, D. Y. J. Am. Chem. Soc. 1997, 119, 7597. 1,2-Anhyrdo glycosyl donors: Du, Y.; Kong, F. Tetrahedron Lett. 1995, 427.
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27. Typical conditions for ortho ester preparation: To a stirred mixture of 1 (238 mg, 0.58 mmol), 6 (188 mg, 0.577 mmol), 2,4-lutidine (68 μL, 0.58 mmol), and molecular sieves (0.2 g) in dichloromethane (6 mL) was added silver triflate (148 mg, 0.58 mmol) under nitrogen atmosphere in a dark room, and the reaction was carried out at room temperature and monitored by TLC (2:1 petroleum ether/ethyl acetate). After completion of the reaction, the mixture was partitioned between dichloromethane and water, and the organic phase was concentrated under reduced pressure. The residual oil was purified by silica gel column chromatography with 2:1 petroleum ether/ ethyl acetate as the eluent, giving the product 7 as an amorphous solid in a yield of 95% (360 mg), capable of being used for further rearrangement.
28. Typical rearrangement conditions: To a stirred solution of sugar-sugar ortho ester 7 (360 mg, 0.55 mmol) in dichloromethane (6 mL) was added TMSOTf (10 μL, 0.1 equiv) at 0 °C under nitrogen atmosphere, and the reaction was monitored by TLC (2:1 petroleum ether/ethyl acetate). After completion of the reaction, to the mixture was added triethylamine (15 μL) and then the mixture was treated at the same way as described in (5), giving 9 in a yield of 78%.
29. 2), 4.24 (dd, H-6′a), 4.16 (dd H-6′b), 4.05 (dd, H-6a), 3.96-3.91 (m, H-5′), 3.78 (dd, H-6b), 3.70-3.66 (m, H-5), 3.52 (t, H-4), 3.48 (dd, H-2).
30. 3CO).
31. Kochetkov, N. K.; Khorlin, A. J.; Bochkov, A. F. Tetrahedron 1967, 23, 693.
32. 16: C, 58.66; H, 5.63. Found: C, 58.76; H, 5.62.
33. 9: C, 63.76; H, 5.60. Found: C, 63.82; H, 5.58], the direct coupling of which with acetobromoglucose in the presence of AgOTf furnished allyl 4-O-acetyl-3-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-2,6-di-O- benzoyl-α-D-glucopyranoside (18), identical with the product obtained from rearrangement of 17.