Simple synthesis of oxiranylidene-2,2-bis(phosphonic acid): Tetrabenzyl geminal bisphosphonate esters as useful intermediates

Philip C. Bulman Page; Michael J. McKenzie; James A. Gallagher

doi:10.1081/SCC-120002004

Simple synthesis of oxiranylidene-2,2-bis(phosphonic acid): Tetrabenzyl geminal bisphosphonate esters as useful intermediates

Philip C. Bulman Page
, Michael J. McKenzie
, James A. Gallagher

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

14 Citations (Scopus)

Abstract

Tetrabenzyl geminal bisphosphonate esters are shown to be useful synthetic equivalents of 1,1-bis(phosphonic acid)s which may be easily functionalized at the central carbon atom without phosphonate ester hydrolysis. The parent bis(phosphonic acid) unit is readily regenerated by hydrogenolysis. The chemistry is used to prepare the elusive epoxide oxiranylidene-2,2-bis(phosphonic acid) by a short and reliable procedure.

Original language	English
Pages (from-to)	211-218
Number of pages	8
Journal	Synthetic Communications
Volume	32
Issue number	2
DOIs	https://doi.org/10.1081/SCC-120002004
Publication status	Published - 2002

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

SDG 3 Good Health and Well-being

Keywords

INHIBITOR
BREAST-CANCER
AGENTS
OSTEOPOROSIS
BONE-RESORPTION
ANALOGS
OVARIECTOMIZED RATS
POSTMENOPAUSAL WOMEN
MECHANISMS
OSTEOBLASTS

Access to Document

10.1081/SCC-120002004

Cite this

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title = "Simple synthesis of oxiranylidene-2,2-bis(phosphonic acid): Tetrabenzyl geminal bisphosphonate esters as useful intermediates",

abstract = "Tetrabenzyl geminal bisphosphonate esters are shown to be useful synthetic equivalents of 1,1-bis(phosphonic acid)s which may be easily functionalized at the central carbon atom without phosphonate ester hydrolysis. The parent bis(phosphonic acid) unit is readily regenerated by hydrogenolysis. The chemistry is used to prepare the elusive epoxide oxiranylidene-2,2-bis(phosphonic acid) by a short and reliable procedure.",

keywords = "INHIBITOR, BREAST-CANCER, AGENTS, OSTEOPOROSIS, BONE-RESORPTION, ANALOGS, OVARIECTOMIZED RATS, POSTMENOPAUSAL WOMEN, MECHANISMS, OSTEOBLASTS",

author = "\{Bulman Page\}, \{Philip C.\} and McKenzie, \{Michael J.\} and Gallagher, \{James A.\}",

year = "2002",

doi = "10.1081/SCC-120002004",

language = "English",

volume = "32",

pages = "211--218",

journal = "Synthetic Communications",

issn = "0039-7911",

publisher = "Taylor and Francis",

number = "2",

}

TY - JOUR

T1 - Simple synthesis of oxiranylidene-2,2-bis(phosphonic acid): Tetrabenzyl geminal bisphosphonate esters as useful intermediates

AU - Bulman Page, Philip C.

AU - McKenzie, Michael J.

AU - Gallagher, James A.

PY - 2002

Y1 - 2002

N2 - Tetrabenzyl geminal bisphosphonate esters are shown to be useful synthetic equivalents of 1,1-bis(phosphonic acid)s which may be easily functionalized at the central carbon atom without phosphonate ester hydrolysis. The parent bis(phosphonic acid) unit is readily regenerated by hydrogenolysis. The chemistry is used to prepare the elusive epoxide oxiranylidene-2,2-bis(phosphonic acid) by a short and reliable procedure.

AB - Tetrabenzyl geminal bisphosphonate esters are shown to be useful synthetic equivalents of 1,1-bis(phosphonic acid)s which may be easily functionalized at the central carbon atom without phosphonate ester hydrolysis. The parent bis(phosphonic acid) unit is readily regenerated by hydrogenolysis. The chemistry is used to prepare the elusive epoxide oxiranylidene-2,2-bis(phosphonic acid) by a short and reliable procedure.

KW - INHIBITOR

KW - BREAST-CANCER

KW - AGENTS

KW - OSTEOPOROSIS

KW - BONE-RESORPTION

KW - ANALOGS

KW - OVARIECTOMIZED RATS

KW - POSTMENOPAUSAL WOMEN

KW - MECHANISMS

KW - OSTEOBLASTS

U2 - 10.1081/SCC-120002004

DO - 10.1081/SCC-120002004

M3 - Article

SN - 0039-7911

VL - 32

SP - 211

EP - 218

JO - Synthetic Communications

JF - Synthetic Communications

IS - 2

ER -