Synthesis of higher carbon sugars from dihydroxyacetone and d-arabinose: An organocatalytic approach
The reaction of 2,3:4,5-diacetone-d-arabinose with protected dihydroxyacetone catalyzed by l-proline afforded two diastereoisomeric octoses in a 7:1 ratio in 75% yield. The anti (3S,4S) configuration at the newly created stereogenic centers was assigned to the main isomer on the basis of the X-ray analysis. The same reaction when catalyzed with unnatural d-proline provided the same products in a 1:20 ratio.
Organocatalytic syn-aldol reactions of dioxanones with (S)-isoserinal hydrate: Synthesis of L-deoxymannojirimycin and L-deoxyidonojirimycin
(Chemical Equation Presented) We report a new protocol for synthesis of L-1-deoxymannojirimycin, L-1-deoxyidonojirimycin, and the N-isopropyl derivative of the latter compound from the readily available precursors (S)-isoserinal hydrate and 2-tert-butyl-2
Palyam, Nagarjuna,Majewski, Marek
supporting information; experimental part
p. 4390 - 4392
(2009/09/06)
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