Novel synthesis of 5-thio-hexopyranoside: Preparation of 5-thio-D- and L-glucose and 1,6-anhydro-5-thio-L- and D-altrose

Tetrahedron

Volumn 59, Issue 35, 2003, Pages 7011-7022

  Uenishi, Jun'ichi ^a   Ohmiya, Hirohisa ^a  

^a KYOTO PHARMACEUTICAL UNIVERSITY   (Japan)

Author keywords

Asymmetric dihydroxylation; D and L 5 thio hexopyranoside; Stereoselective synthesis; Thiosugar

Indexed keywords

1,6 ANHYDRO 5 THIOALTROSE; 5 THIOHEXOPYRANOSIDE; ACETAL DERIVATIVE; ACETIC ACID; ALCOHOL DERIVATIVE; ARABINOSE; GAMMA HYDROXYCROTYLALDEHYDE DIETHYLACETAL; GAMMA THIIRANYLDIETHYLACETAL; GLUCOSE DERIVATIVE; PYRANOSIDE; THIOGLUCOSE; UNCLASSIFIED DRUG; XYLOSE;

ARTICLE; ASYMMETRIC SYNTHESIS; CARBON NUCLEAR MAGNETIC RESONANCE; CYCLIZATION; DRUG HYDROXYLATION; DRUG SYNTHESIS; DRUG TRANSFORMATION; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; THIN LAYER CHROMATOGRAPHY; ULTRAVIOLET SPECTROPHOTOMETRY;

EID: 0043160218     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(03)00864-0     Document Type: Article

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39. 1H NMR spectrum were in good accordance with methyl 2,3,4,6-O-tetraacetyl-5-thio-β-D-altrose reported by Hughes, see: Al-Masoudi N.A.L., Hughes N.A. Carbohydr. Res. 148:1986;39-49.
40. Since compounds D-2′ and L-2′ are quite stable in acidic conditions, their hydrolysis leading to D-2′ and L-2′ have not been successful.