138963-02-7Relevant academic research and scientific papers
A Domino Epoxide Ring-Opening Xanthate Migration Reaction: An Alternative Entry to Thiosugars
Comba, María B.,Mangione, María I.,Suárez, Alejandra G.,Sarotti, Ariel M.,Spanevello, Rolando A.
, p. 6848 - 6856 (2018/12/11)
A sterereospecific and efficient synthesis of thiosugars derived from levoglucosenone and methyl α-d-glucopyranoside was developed by a domino epoxide ring opening- xanthate migration to afford 1,3-oxathiolane-2-thiones in high yields. The stereochemical outcome of the new C–S bond was defined by the configuration of the starting materials. The 1,3-oxathiolane-2-thiones were subsequently submitted to a second tandem reaction affording the corresponding 2,3-episulfide alcohols. The thiosugars obtained are useful building blocks for the synthesis of thiooligosaccharides with potential biological properties.
Method of manufacturing D-allosan
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, (2008/06/13)
The carbonyl group at the 2-position of levoglucosenone is reduced to obtain a hydroxyl group having a β-configuration. The hydroxyl group having a β-configuration is reversed to an α-configuration, and hydroxyl groups are added at the 3- and 4-positions
SYNTHESIS OF D-ALLOSAN FROM LEVOGLUCOSENONE
Matsumoto, Katsuya,Ebata, Takashi,Koseki, Koshi,Kawakami, Hiroshi,Matsushita, Hajime
, p. 2225 - 2240 (2007/10/02)
The stereoselective reduction and cis-dihydroxylation of levoglucosenone (1,6-anhydro-3,4-dideoxy-β-D-glycero-hex-3-enopyranos-2-ulose), gave D-allosan (1,6-anhydro-β-D-allopyranose) in high yield.
