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Efficient Synthesis of Optically Pure (4 R ,6 S )-4-( tert -Butyldimethylsilyloxy)- 6-(hydroxymethyl)tetrahydropyran-2-one and Its Enantiomer

✍ Scribed by Ghorpade, Sandeep R.; Kalkote, Uttam R.; Chavan, Subhash P.; Bhide, Sunil R.; Ravindranathan, T.; Puranik, Veda G.


Book ID
127163153
Publisher
American Chemical Society
Year
2001
Tongue
English
Weight
51 KB
Volume
66
Category
Article
ISSN
0022-3263

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Syntheses of 4(R)-silyloxy-6(S)-iodometh
✍ E Baader; W Bartmann; G Beck; A Bergmann; H.-W Fehlhaber; H Jendralla; K Kessele πŸ“‚ Article πŸ“… 1988 πŸ› Elsevier Science 🌐 French βš– 176 KB

Optically pure 4(R),6(S)-iodolactone 1 was obtained from a-D-(+)-glucose in 17 steps with 17% overall yield. Its enantiomere4(S),6(R)-iodolactone 1' was obtained from acetonedicarboxylic acid in 9 steps in 37% overall yield and witTi\_70% ee. Key steps in the synthesis of 1' are enzyme (PLE)-catalyz