Synthesis of α-hydroxy(polyprenyl) bisphosphonates

O. O. Kolodyazhnaya; O. I. Kolodyazhnyi; R. A. Cherkasov; A. R. Garifzyanov; N. V. Davletshina; S. A. Koshkin

doi:10.1134/S1070363214040082

Synthesis of α-hydroxy(polyprenyl) bisphosphonates

O. O. Kolodyazhnaya
, O. I. Kolodyazhnyi
, R. A. Cherkasov
, A. R. Garifzyanov
, N. V. Davletshina
, S. A. Koshkin

Huck Institutes of the Life Sciences

Research output: Contribution to journal › Article › peer-review

2 Scopus citations

Abstract

Bisphosphonates derived from natural terpenes were synthesized by phosphonylation of corresponding aldehydes. The general strategy of introduction of the phosphonate groups into the polyprenol molecule involves successive treatment of a hydroxyl compound by Swern reagent to oxidize the C-OH group into C=O and a (EtO)₃P/[PyH]⁺ClO _- ⁴ mixture to phosphylate the resulting carbonyl compound.

Original language	English (US)
Pages (from-to)	647-653
Number of pages	7
Journal	Russian Journal of General Chemistry
Volume	84
Issue number	4
DOIs	https://doi.org/10.1134/S1070363214040082
State	Published - Apr 2014

All Science Journal Classification (ASJC) codes

General Chemistry

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10.1134/S1070363214040082

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@article{e867fcd13dfe4522bfcddc60f66371b4,

title = "Synthesis of α-hydroxy(polyprenyl) bisphosphonates",

abstract = "Bisphosphonates derived from natural terpenes were synthesized by phosphonylation of corresponding aldehydes. The general strategy of introduction of the phosphonate groups into the polyprenol molecule involves successive treatment of a hydroxyl compound by Swern reagent to oxidize the C-OH group into C=O and a (EtO)3P/[PyH]+ClO - 4 mixture to phosphylate the resulting carbonyl compound.",

author = "Kolodyazhnaya, \{O. O.\} and Kolodyazhnyi, \{O. I.\} and Cherkasov, \{R. A.\} and Garifzyanov, \{A. R.\} and Davletshina, \{N. V.\} and Koshkin, \{S. A.\}",

note = "Funding Information: The work was financially supported by the State Foundation for Basic Research of Ukraine (project no. F53.3/016) and Russian Foundation for Basic Research (project no. 13-03-90448).",

year = "2014",

month = apr,

doi = "10.1134/S1070363214040082",

language = "English (US)",

volume = "84",

pages = "647--653",

journal = "Russian Journal of General Chemistry",

issn = "1070-3632",

publisher = "Pleiades Publishing",

number = "4",

}

TY - JOUR

T1 - Synthesis of α-hydroxy(polyprenyl) bisphosphonates

AU - Kolodyazhnaya, O. O.

AU - Kolodyazhnyi, O. I.

AU - Cherkasov, R. A.

AU - Garifzyanov, A. R.

AU - Davletshina, N. V.

AU - Koshkin, S. A.

N1 - Funding Information: The work was financially supported by the State Foundation for Basic Research of Ukraine (project no. F53.3/016) and Russian Foundation for Basic Research (project no. 13-03-90448).

PY - 2014/4

Y1 - 2014/4

N2 - Bisphosphonates derived from natural terpenes were synthesized by phosphonylation of corresponding aldehydes. The general strategy of introduction of the phosphonate groups into the polyprenol molecule involves successive treatment of a hydroxyl compound by Swern reagent to oxidize the C-OH group into C=O and a (EtO)3P/[PyH]+ClO - 4 mixture to phosphylate the resulting carbonyl compound.

AB - Bisphosphonates derived from natural terpenes were synthesized by phosphonylation of corresponding aldehydes. The general strategy of introduction of the phosphonate groups into the polyprenol molecule involves successive treatment of a hydroxyl compound by Swern reagent to oxidize the C-OH group into C=O and a (EtO)3P/[PyH]+ClO - 4 mixture to phosphylate the resulting carbonyl compound.

UR - https://www.scopus.com/pages/publications/84901032592

UR - https://www.scopus.com/pages/publications/84901032592#tab=citedBy

U2 - 10.1134/S1070363214040082

DO - 10.1134/S1070363214040082

M3 - Article

AN - SCOPUS:84901032592

SN - 1070-3632

VL - 84

SP - 647

EP - 653

JO - Russian Journal of General Chemistry

JF - Russian Journal of General Chemistry

IS - 4

ER -

Synthesis of α-hydroxy(polyprenyl) bisphosphonates

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