Details

Autor(en) / Beteiligte

• Lipták, András
• Sajtos, Ferenc
• Jánossy, Lóránt
• Gehle, Diethmar
• Szilágyi, László

Titel

A General Method for the Synthesis of Sugar 2-C-Sulfonic Acids by 1 → 2 Arylthio Group Migration in Acid-Sensitive Thioglycosides. Direct Transformation of Thiotrityl Ethers into C-Sulfonic Acids

Ist Teil von

• Organic letters, 2003-10, Vol.5 (20), p.3671-3674

Ort / Verlag

United States: American Chemical Society

Erscheinungsjahr

2003

Link zum Volltext

Quelle

Alma/SFX Local Collection

Beschreibungen/Notizen

• Fully protected triphenylmethyl 2-O-mesyl-1-thio-β-d-gluco- (14) and -α-d-mannopyranoside (28) were transformed by a stereoselective intramolecular 1 → 2 trans-arylthio migration into methyl 2-S-triphenylmethyl-α-d-manno- (15) and -β-d-glucopyranoside (29), respectively, using NaOCH3 as nucleophile. The 2-S-triphenylmethyl ethers (15 and 29) were directly oxidized to sugar 2-C-sulfonic acids by using oxone (2KHSO5, KHSO4, K2SO4). Compounds (21, 23, 32, and 35) are the first representatives of secondary sugar C-sulfonic acids.