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Kinetically controlled Ferrier rearrangement of 3-O-mesyl-D-glycal derivatives.
Carbohydr Res. 2009 Mar 10; 344(4):516-20.CR

Abstract

The Ferrier rearrangement, which is widely used in carbohydrate chemistry, is generally performed under acidic conditions to give an alpha anomer with high stereoselectivity. We have found that 3-O-mesyl-D-glycals 2-4 were smoothly reacted with alcohols in the presence of triethylamine. The present reaction was shown to proceed under kinetic control to give approximately 1.3:1.0 mixture of alpha and beta anomers, indicating that a kinetic anomeric effect does not operate.

Authors+Show Affiliations

Graduate School of Integrated Science, Yokohama City University, Kanazawa-ku, Yokohama, Japan.No affiliation info availableNo affiliation info available

Pub Type(s)

Journal Article

Language

eng

PubMed ID

19185852

Citation

Watanabe, Yuhya, et al. "Kinetically Controlled Ferrier Rearrangement of 3-O-mesyl-D-glycal Derivatives." Carbohydrate Research, vol. 344, no. 4, 2009, pp. 516-20.
Watanabe Y, Itoh T, Sakakibara T. Kinetically controlled Ferrier rearrangement of 3-O-mesyl-D-glycal derivatives. Carbohydr Res. 2009;344(4):516-20.
Watanabe, Y., Itoh, T., & Sakakibara, T. (2009). Kinetically controlled Ferrier rearrangement of 3-O-mesyl-D-glycal derivatives. Carbohydrate Research, 344(4), 516-20. https://doi.org/10.1016/j.carres.2008.12.015
Watanabe Y, Itoh T, Sakakibara T. Kinetically Controlled Ferrier Rearrangement of 3-O-mesyl-D-glycal Derivatives. Carbohydr Res. 2009 Mar 10;344(4):516-20. PubMed PMID: 19185852.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Kinetically controlled Ferrier rearrangement of 3-O-mesyl-D-glycal derivatives. AU - Watanabe,Yuhya, AU - Itoh,Tsubasa, AU - Sakakibara,Tohru, Y1 - 2008/12/25/ PY - 2008/10/01/received PY - 2008/12/13/revised PY - 2008/12/16/accepted PY - 2009/2/3/entrez PY - 2009/2/3/pubmed PY - 2009/5/15/medline SP - 516 EP - 20 JF - Carbohydrate research JO - Carbohydr. Res. VL - 344 IS - 4 N2 - The Ferrier rearrangement, which is widely used in carbohydrate chemistry, is generally performed under acidic conditions to give an alpha anomer with high stereoselectivity. We have found that 3-O-mesyl-D-glycals 2-4 were smoothly reacted with alcohols in the presence of triethylamine. The present reaction was shown to proceed under kinetic control to give approximately 1.3:1.0 mixture of alpha and beta anomers, indicating that a kinetic anomeric effect does not operate. SN - 1873-426X UR - https://www.unboundmedicine.com/medline/citation/19185852/Kinetically_controlled_Ferrier_rearrangement_of_3_O_mesyl_D_glycal_derivatives_ L2 - https://linkinghub.elsevier.com/retrieve/pii/S0008-6215(08)00593-4 DB - PRIME DP - Unbound Medicine ER -