Divergent synthesis of (L)-sugars and (L)-iminosugars from D-sugars

An efficient divergent synthesis Of L-sugars and L-iminosugars from D-sugars is described. The important intermediate, delta-hydroxyalkoxamate, prepared from D-glucono-/galactono-1,5-lactone, was cyclized under Mitsunobu conditions to give the O-cyclized oxime compound and the N-cyclized lactam comp...

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Published inChemistry : a European journal Vol. 12; no. 22; pp. 5868 - 5877
Main Authors Takahashi, Hideyo, Shida, Tomomi, Hitomi, Yuko, Iwai, Yoshinori, Miyama, Namisa, Nishiyama, Kazusa, Sawada, Daisuke, Ikegami, Shiro
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 24.07.2006
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
carbohydrates
ORGANIC-SYNTHESIS
PRACTICAL SYNTHESIS
Mitsunobu reaction
EFFICIENT SYNTHESIS
TRANSITION-STATE
HEPARIN
BLEOMYCIN A
L-HEXOSES
lactams
lactones
BIOLOGICAL-ACTIVITY
CHEMICAL-SYNTHESIS
azasugars
BETA-LACTAMS
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Summary:An efficient divergent synthesis Of L-sugars and L-iminosugars from D-sugars is described. The important intermediate, delta-hydroxyalkoxamate, prepared from D-glucono-/galactono-1,5-lactone, was cyclized under Mitsunobu conditions to give the O-cyclized oxime compound and the N-cyclized lactam compound as mixtures. A more detailed investigation revealed that the appropriate protecting groups and solvents controlled the specificity for the O-/N-cyclization of the delta-hydroxyalkoxamate. Suitable protection at the delta-position of 6-hydroxyalkoxamate, derived from D-glucono-1,5-lactone, afforded the corresponding delta-alkylation product alone. Thus we succeeded in applying this to the total synthesis of L-iduronic acid. In contrast, with both TBDMS as the protecting group and RCN as the solvent the efficient conversion of D-glucono/galactono-1,5-lactone into the corresponding L-iminosugars (L-idonolactam and L-altronolactam) was achieved.
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.200600268