Syntheses of difluorinated carbasugar phosphates from trifluoroethanol

Timo Anderl, Christophe Audouard, Afjal Miah, Jonathan M. Percy, Giuseppe Rinaudo, Kuldip. Singh

Research output: Contribution to journalArticle

7 Citations (Scopus)

Abstract

Difluorinated cyclohexene diols (prepd. from trifluoroethanol) can be elaborated to racemic analogs of phosphorylated sugars via regioselective protection and phosphorylation of the exposed C-1 hydroxyl group. Cis-diol protection was achieved using stannylene methodol., though the regioselectivity depended on the orientation of the Me group at C-5. UpJohn dihydroxylation is effective with the phosphotriester in place and global deprotection to the tetrol monophosphates I (R1 = OH, R2 = H; R1 = H, R2 = OH) is efficient.
LanguageUndefined/Unknown
Pages5200-5206
Number of pages7
JournalOrganic and Biomolecular Chemistry
Volume7
Issue number24
DOIs
Publication statusPublished - 2009

Keywords

  • trifluoroethanol
  • difluorinated carbasugar phosphates
  • phosphorylated sugars
  • monophosphates

Cite this

Anderl, T., Audouard, C., Miah, A., Percy, J. M., Rinaudo, G., & Singh, K. (2009). Syntheses of difluorinated carbasugar phosphates from trifluoroethanol. Organic and Biomolecular Chemistry, 7(24), 5200-5206. https://doi.org/10.1039/b914068a
Anderl, Timo ; Audouard, Christophe ; Miah, Afjal ; Percy, Jonathan M. ; Rinaudo, Giuseppe ; Singh, Kuldip. / Syntheses of difluorinated carbasugar phosphates from trifluoroethanol. In: Organic and Biomolecular Chemistry. 2009 ; Vol. 7, No. 24. pp. 5200-5206.
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Anderl, T, Audouard, C, Miah, A, Percy, JM, Rinaudo, G & Singh, K 2009, 'Syntheses of difluorinated carbasugar phosphates from trifluoroethanol' Organic and Biomolecular Chemistry, vol. 7, no. 24, pp. 5200-5206. https://doi.org/10.1039/b914068a

Syntheses of difluorinated carbasugar phosphates from trifluoroethanol. / Anderl, Timo; Audouard, Christophe; Miah, Afjal; Percy, Jonathan M.; Rinaudo, Giuseppe; Singh, Kuldip.

In: Organic and Biomolecular Chemistry, Vol. 7, No. 24, 2009, p. 5200-5206.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Syntheses of difluorinated carbasugar phosphates from trifluoroethanol

AU - Anderl, Timo

AU - Audouard, Christophe

AU - Miah, Afjal

AU - Percy, Jonathan M.

AU - Rinaudo, Giuseppe

AU - Singh, Kuldip.

PY - 2009

Y1 - 2009

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AB - Difluorinated cyclohexene diols (prepd. from trifluoroethanol) can be elaborated to racemic analogs of phosphorylated sugars via regioselective protection and phosphorylation of the exposed C-1 hydroxyl group. Cis-diol protection was achieved using stannylene methodol., though the regioselectivity depended on the orientation of the Me group at C-5. UpJohn dihydroxylation is effective with the phosphotriester in place and global deprotection to the tetrol monophosphates I (R1 = OH, R2 = H; R1 = H, R2 = OH) is efficient.

KW - trifluoroethanol

KW - difluorinated carbasugar phosphates

KW - phosphorylated sugars

KW - monophosphates

U2 - 10.1039/b914068a

DO - 10.1039/b914068a

M3 - Article

VL - 7

SP - 5200

EP - 5206

JO - Organic and Biomolecular Chemistry

T2 - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

SN - 1477-0520

IS - 24

ER -