Journal ArticleDOI
Synthesis of α‐2‐Deoxyglycosides by Acid‐Mediated Conjugate Addition
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TLDR
In this article, a new method for the synthesis of α−2−deoxyglycosides from hex−1−en−3−uloses is reported. But the method is not suitable for α,β−unsaturated ketones.About:
This article is published in Journal of Carbohydrate Chemistry.The article was published on 2005-03-01. It has received 7 citations till now. The article focuses on the topics: Glucal & Conjugate.read more
Citations
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Journal ArticleDOI
Protecting group and solvent control of stereo- and chemoselectivity in glucal 3-carbamate amidoglycosylation.
TL;DR: In the Rh(2)(OAc)(4)-catalyzed amidoglycosylation of glucal 3-carbamates, anomeric stereoselectivity and the extent of competing C3-H oxidation depend on the 4O and 6O protecting groups, which permits high alpha-anomer selectivity with further improvement in less polar solvents.
Journal ArticleDOI
Ready access to 3-amino-2,3-dideoxysugars via regio- and stereo-selective tandem hydroamination–glycosylation of glycals
TL;DR: A highly stereoselective BF(3)·OEt(2)-promoted tandem hydroamination-glycosylation on a glycal scaffold has been developed to form 3-amino-2,3-dideoxysugars in a one-pot procedure that offers simplicity and general applicability to a broad range of variations on each component.
Journal ArticleDOI
Microwave-assisted stereoselective α-2-deoxyglycosylation of hex-1-en-3-uloses
Hui-Chang Lin,Hsu-Hsuan Wu,Zi-Ping Lin,Chih-Yuan Lin,Chun-Hung Lin,Kun-Lung Chen,Fung Fuh Wong +6 more
TL;DR: In this article, α-2-deoxy glycosides were successfully synthesized by means of microwave-assisted glycosylation by treating Hex-1-en-3-uloses with a catalytic amount of AlCl 3 and various O -nucleophiles including alcohols and sugars under microwave conditions.
Journal ArticleDOI
Synthesis of new 2-phosphono-α-d-glycoside derivatives by stereoselective oxa-Michael addition to a d-galacto derived enone
TL;DR: The synthesis of new 2-phosphono-alpha-D-glycoside derivatives by stereoselective oxa-Michael addition to an enone derived from D-galactal and containing a phosphonate group is described.
Journal ArticleDOI
Synthesis of α-2-deoxy-ulosides by Michael addition of hex-1-en-3-ones
Zi-Ping Lin,Fung Fuh Wong,Yen-Bo Chen,Yu-Cheng Lin,Masayuki Kimura,Kimiyoshi Kaneko,Hiroyuki Takayama,Jin-Bin Wu,Chun-Hung Lin,Hui-Chang Lin +9 more
TL;DR: In this paper, α-2-deoxyulosides were synthesized in moderate to good yields by adding various O -nucleophiles to hex-1-en-3-ones in the presence of NaOH.
References
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Journal ArticleDOI
Synthesis of Branched-Chain Sugars
TL;DR: An overview of the synthesis of branched-chain sugars can be found in this article, where the concepts related to the nucleophilic reactions of sugar oxiranes, aldol addition, and cyclization of dialdehydes with nitroalkanes are discussed.
Book
Bioactive Carbohydrates: In Chemistry, Biochemistry and Biology
John F. Kennedy,Charles A. White +1 more