Tetrahedron

… , 6-O-benzylidene-2, 3-dideoxy-5-thio-β-dl-threo-hex-2-enopyranoside via hetero-Diels–Alder reaction and unusual stabilities of 1, 5-anhydro-4, 6-O-benzylidene 2, 3- …

Y Watanabe, T Sakakibara

Index: Watanabe, Yuhya; Sakakibara, Tohru Tetrahedron, 2009 , vol. 65, # 3 p. 599 - 606

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Citation Number: 11

Abstract

The title compound was prepared via hetero-Diels–Alder reaction of 1-acetoxy-1, 3- butadiene and thioaldehyde, followed by Pummerer rearrangement. Different from the corresponding sugar and 5a-carba sugar, C-inside isomer of 1, 5-anhydro-4, 6-O- benzylidene-2, 3-dideoxy-5-thio-dl-thero-hex-2-enitol was found to be thermodynamically more stable than the corresponding O-inside one and these thermodynamic stabilities ...