Pummerer rearrangement of 1-deoxy-5-thioglucopyranose oxides; Novel synthesis of 5-thioglucopyranose derivatives

Tetrahedron Letters

Volumn 44, Issue 21, 2003, Pages 4089-4093

  Matsuda, Hiroko ^a   Fujita, Junji ^a   Morii, Yasuharu ^a   Hashimoto, Masaru ^a   Okuno, Toshikatsu ^a   Hashimoto, Kimiko ^b  

^a HIROSAKI UNIVERSITY   (Japan)

^b RIKEN Center for Sustainable Resource Science   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

1 DEOXY 5 THIOGLUCOPYRANOSE OXIDE; CARBOHYDRATE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CARBOHYDRATE SYNTHESIS; CARBON NUCLEAR MAGNETIC RESONANCE; PROTON NUCLEAR MAGNETIC RESONANCE; PUMMERER REACTION; STEREOCHEMISTRY;

EID: 0037652240     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)00842-6     Document Type: Article

References (15)

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12. Actually, treatment of 6b with triethylamine in MeOH gave 8b (8.0%), 9b (17%), recovered 6b (25%), and methyl ether 11 (12%).
13. +): 411.1114, found m/z=411.1137.
14. PC Spartan Pro version 1.08 by Wavefunction Inc. was used for the calculations. Since some model compounds employed for the calculations involved a sulfoxide function, ab initio method based on the 6-31G* basis set was employed by taking the accuracy into account. When 6-31G* was employed, optimization for these model compounds required 20-60 h by our systems (Athron XP 1800+, 256 Mb RAM). Since conformation search by AM1 for sulfide X gave many stable conformations (15 conformations), only the conformation found as the most stable by the above calculations was re-optimized by 6-31G* for sulfide and sulfoxides X . Conformation searches for model sulfides Y and Z could be performed directly with 6-31G*, providing three and five stable conformations, respectively. The conformations with minimum energies found by the above calculations were employed as the initial geometries for optimization of the corresponding sulfoxides.
15. -) also might be important for this kind of consideration.