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Glycosylations of Glycals using N-Iodosuccinimide (NIS) and Phosphorus Compounds for Syntheses of 2-Iodo- and 2-Deoxyglycosides.
Kimura, Tomoya; Takahashi, Daisuke; Toshima, Kazunobu.
Affiliation
  • Kimura T; Department of Applied Chemistry, Faculty of Science and Technology, Keio University , 3-14-1 Hiyoshi, Kohoku-ku, Yokohama 223-8522, Japan.
  • Takahashi D; Department of Applied Chemistry, Faculty of Science and Technology, Keio University , 3-14-1 Hiyoshi, Kohoku-ku, Yokohama 223-8522, Japan.
  • Toshima K; Department of Applied Chemistry, Faculty of Science and Technology, Keio University , 3-14-1 Hiyoshi, Kohoku-ku, Yokohama 223-8522, Japan.
J Org Chem ; 80(19): 9552-62, 2015 Oct 02.
Article in En | MEDLINE | ID: mdl-26375399
ABSTRACT
The glycosylations of glycals and alcohols using N-iodosuccinimide (NIS) and a catalytic amount of PPh3 effectively proceeded under mild conditions to provide the corresponding 2-deoxy-2-iodoglycosides in high yields. The reactivity of the iodoglycosylations with PPh3 significantly increased in comparison to that using NIS alone as an activator. In addition, the glycosylations of glycals and alcohols using catalytic amounts of NIS and P(OPh)3 were effectively realized to give the corresponding 2-deoxyglycosides in high yields.
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Full text: 1 Collection: 01-internacional Database: MEDLINE Language: En Journal: J Org Chem Year: 2015 Type: Article Affiliation country: Japan
Fulltext
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PubMed Links
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Full text: 1 Collection: 01-internacional Database: MEDLINE Language: En Journal: J Org Chem Year: 2015 Type: Article Affiliation country: Japan