A new synthesis of the cyclitol ring-system

Kiely, Donald E.; Cantrell, Charles E.

doi:10.1016/s0008-6215(00)81589-x

Cited by 6 publications

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“…It is worthy to note that the tertiary hydroxy group in myo -18 and scyllo -18 remained unprotected under these conditions. The literature data are rather contradictory concerning the acetylation of this tertiary alcohol using acetic anhydride [ 50 – 51 ]. With regard to a PET application, the protection of this hydroxy group is of paramount importance since the free hydroxy group could impair the incorporation of the radioactive fluorine.…”

Section: Resultsmentioning

confidence: 99%

Diastereoselective synthesis of new O-alkylated and C-branched inositols and their corresponding fluoro analogues

Collet¹,

Chrétien²,

Chapleur³

et al. 2016

Beilstein J. Org. Chem.

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SummaryEfficient routes were developed for the diastereoselective synthesis of new O-alkylated and C-branched inositols and their corresponding fluoro analogues. The key steps of the synthesis were the easy accessibility of different types of arms in term of configuration (myo and scyllo), the linking method and length, which could modulate the biological properties. These inositol derivatives, bearing an arm terminated either with a hydroxy group or a fluorine atom, could be interesting candidates for diastereoisomeric intermediates and biological evaluations, especially for PET imaging experiments.

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Section: Resultsmentioning

confidence: 99%

Diastereoselective synthesis of new O-alkylated and C-branched inositols and their corresponding fluoro analogues

Collet¹,

Chrétien²,

Chapleur³

et al. 2016

Beilstein J. Org. Chem.

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The Total Synthesis of Carbohydrates 1972–1980

Zamojski

Grynkiewicz

1984

Total Synthesis of Natural Products

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Synthesis of a Glyoxalase I Inhibitor from Streptomyces griseosporeus NIIDAet OGASAWARA

Mirza

Molleyres

Vasella

1985

Helvetica Chimica Acta

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The pseudolactones 6 and 12 were prepared in a straightforward way from methyl α‐D‐glucopyranoside and methyl α‐D‐mannopyranoside, respectively. The pseudolactone 6 reacted with tert‐butyl lithioacetate to give the protected, trihydroxylated cyclohexenone carboxylate 7 (51 %). The sterically hindered, L‐ribo‐configurated pseudolactone 12 reacted with diethyl ethylphosphonate and dimethyl methylphosphonate to give the protected trihydroxycyclohexenones 17 (49 %) and 18 (62 %), respectively. The hydroxymethylated cyclohexenone 21 was obtained from 18 by treatment with Me2AlSPh and then formaldehyde, oxidation of the product 19, and elimination. Deprotection of 21 gave 2, identical with KD16‐Ul. Esterification of 2 gave 1, identical with the title compound. Alternatively, 1 was obtained in higher yields by esterification of 21, followed by deprotection of the hydroxy groups. This synthesis gave 1 and 2 from methyl α‐D‐mannopyranoside in an overall yield of 18 and 20 %, respectively, confirming their absolute configuration.

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A new synthesis of the cyclitol ring-system

Cited by 6 publications

References 0 publications

Diastereoselective synthesis of new O-alkylated and C-branched inositols and their corresponding fluoro analogues

Diastereoselective synthesis of new O-alkylated and C-branched inositols and their corresponding fluoro analogues

The Total Synthesis of Carbohydrates 1972–1980

Synthesis of a Glyoxalase I Inhibitor from Streptomyces griseosporeus NIIDAet OGASAWARA

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