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ChemInform Abstract: Diastereoselective Propargylation of Sugar Aldehydes. New Synthesis of 6-Deoxyheptoses.

โœ Scribed by Z. PAKULSKI; A. ZAMOJSKI

Book ID
101841850
Publisher
John Wiley and Sons
Year
2010
Weight
35 KB
Volume
28
Category
Article
ISSN
0931-7597

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โœฆ Synopsis

Diastereoselective Propargylation of Sugar Aldehydes. New Synthesis of 6-Deoxyheptoses.

-Treatment of sugar aldehydes with propargyl bromide in the presence of Zn is found to give homopropargylic alcohols in good yields. Products with D-manno, D-gluco, as well as D-altro configurations are obtained with excellent diastereoselectivity (anti:syn = ยฟ 20:1). Hydrogenation of the triple bond yields homoallylic alcohols like (VIII) which are useful intermediates in the synthesis of 6-deoxyheptoses. Ozonolysis of the triple bond leads to 6-deoxyhepturonic esters.

-(PAKULSKI, Z.; ZAMOJSKI,

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ChemInform Abstract: Synthesis of 6-Deoxyheptose Derivatives via Cyclic Sulfates and Oxetanes.
โœ Antonio Vargas-Berenguel; Francisco Santoyo-Gonzalez; Jose A. Calvo-Asin; Franci ๐Ÿ“‚ Article ๐Ÿ“… 2010 ๐Ÿ› John Wiley and Sons โš– 31 KB ๐Ÿ‘ 2 views

Synthesis of 6-Deoxyheptose Derivatives via Cyclic Sulfates and Oxetanes. -Two methods for chain elongation and synthesis of 6deoxyheptoses are detailed. The first approach is based on a regioselective opening of 4,6-cyclic sulfates [cf. (I)] and the second one involves a ring expansion of oxiranes