Enantioselective synthesis of inositols as intermediates for the preparation of deoxy-inositol phosphates from D-galactose

Cléophax, J.; Dubreuil, Didier; Géro, S. D.; Loupy, André; Almeida, Mauro Vieira de; Silva, Adison D. Da; Vass, G.; Bischoff, Erwin; Perzbom, Elisabeth; Hecker, G; Lockhoff, Oswald

doi:10.1016/0960-894x(95)00120-i

Cited by 13 publications

(2 citation statements)

References 26 publications

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“…The synthesis of this compound will give us some information on the influence of the OH in position 6 on the ionization state of the phosphate groups and its possible influence on the cooperation among the phosphates. Its synthesis has been previously reported starting from benzene or from galactose, , while our starting material was myo- inositol ( 9 ) (Scheme ). The myo- inositol was converted into 1,4,5-tri- O -benzyl-2,3- O -isopropylidene- myo- inositol ( 10 ) using the following conditions.…”

Section: Synthesismentioning

confidence: 99%

Synthesis, Acid−Base Behavior, and Binding Properties of 6-Modified myo-Inositol 1,4,5-Tris(phosphate)s

et al. 1999

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myo-Inositol 1,4,5-tris(phosphate) was modified at position 6. The analogues synthesized are reported in this publication are 6-deoxy-myo-inositol 1,4,5-tris(phosphate), 6-fluoro-6-deoxy-myo-inositol 1,4,5-tris(phosphate), epi-inositol 1, 4,5-tris(phosphate), and 6-amino-6-deoxy-myo-inositol 1,4, 5-tris(phosphate). These derivatives showed poor affinity for the Ins(1,4,5)P(3) receptors. The inframolecular acid-base behavior and the cooperative effects between the phosphate groups could help explain the loss of affinity of these 6-modified analogues.

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Section: Synthesismentioning

confidence: 99%

Synthesis, Acid−Base Behavior, and Binding Properties of 6-Modified myo-Inositol 1,4,5-Tris(phosphate)s

et al. 1999

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“…110 Οι Da Silva και Gero χρησιµοποιούν και αυτοί την αναδιάταξη τύπου Ferrier, αλλά σε διαφορετικό παράγωγο της D-γλυκόζης. 111 Η λογική είναι παρόµοια και η σύνθεση ξεκινά και σ' αυτήν την περίπτωση από το µεθυλο-α-D-γλυκοζίτη 309 (Σχήµα 46). ∆ύο από τα υδροξύλια (που θα µετατραπούν στα ΟΗ-2 και ΟΗ-3 του ινοσιτολικού σκελετού) προστατεύονται µε κυκλοεξυλιδενοκετάλη (320).…”

Section: ορθοβενζοϊκοί εστέρεςunclassified

Σύνθεση φωσφορυλιωμένων παραγώγων της myo-ινοσιτόλης

Βάρβογλη¹

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ChemInform Abstract: Enantioselective Synthesis of Inositols as Intermediates for the Preparation of Deoxy‐inositol Phosphates from D‐Galactose.

Cléophax¹,

Dubreuil²,

Géro³

et al. 1995

ChemInform

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Enantioselective Synthesis of Inositols as Intermediates for the Preparation of Deoxy-inositol Phosphates from D-Galactose. -Products (IV), (VI) and (VII) are suitable intermediates for the preparation of a series of polyphosphate analogues. Key step is the Ferrier rearrangement of the exocyclic olefin (II) under changed conditions. -(CLEOPHAX, J.; DUBREUIL, D.; GERO, S. D.; LOUPY, A.; VIEIRA DE ALMEIDA, M.; DA SILVA, A. D.; VASS, G.; Bioorg. Med. Chem. Lett. 5 (1995) 8, 831-834; Inst. Chim. Subst. Nat., CNRS, F-91198 Gif-sur-Yvette, Fr.; EN)

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Enantioselective synthesis of inositols as intermediates for the preparation of deoxy-inositol phosphates from D-galactose

Cited by 13 publications

References 26 publications

Synthesis, Acid−Base Behavior, and Binding Properties of 6-Modified myo-Inositol 1,4,5-Tris(phosphate)s

Synthesis, Acid−Base Behavior, and Binding Properties of 6-Modified myo-Inositol 1,4,5-Tris(phosphate)s

Σύνθεση φωσφορυλιωμένων παραγώγων της myo-ινοσιτόλης

ChemInform Abstract: Enantioselective Synthesis of Inositols as Intermediates for the Preparation of Deoxy‐inositol Phosphates from D‐Galactose.

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