Synthesis of rac-1-(9-o-carboranyl)nonyl-2-methyl-glycero-3-phosphocholine (B-Et-11-OMe), a potential boron carrier for Boron Neutron Capture Therapy (BNCT)

Peter Lemmen; Birgit Werner

doi:10.1016/0009-3084(92)90096-8

Synthesis of rac-1-(9-o-carboranyl)nonyl-2-methyl-glycero-3-phosphocholine (B-Et-11-OMe), a potential boron carrier for Boron Neutron Capture Therapy (BNCT)

Peter Lemmen
, Birgit Werner

Natural Sciences

Technical University of Munich

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

13 Scopus citations

Abstract

Boron-containing analogues of ether lipids are proposed as boron carriers in the boron neutron capture therapy (BNCT). The synthesis of rac-1-(9-o-Carboranyl)nonyl-2-methyl-glycero- 3-phosphocholine (B-Et-11-OMe) as a first representative is described. The carborane is introduced into the readily assembled glycerol ether moiety. The phosphocholine headgroup is introduced by 2-chloro-3-methyl-1,3,2-λ³-oxazaphospholane using a phosphoamidite strategy and subsequent ring opening under alkylating conditions.

Original language	English
Pages (from-to)	185-191
Number of pages	7
Journal	Chemistry and Physics of Lipids
Volume	62
Issue number	2
DOIs	https://doi.org/10.1016/0009-3084(92)90096-8
State	Published - Sep 1992

Keywords

BNCT
boron neutron capture therapy
ether lipid
glycidyl ether
phosphoamidite

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10.1016/0009-3084(92)90096-8

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title = "Synthesis of rac-1-(9-o-carboranyl)nonyl-2-methyl-glycero-3-phosphocholine (B-Et-11-OMe), a potential boron carrier for Boron Neutron Capture Therapy (BNCT)",

abstract = "Boron-containing analogues of ether lipids are proposed as boron carriers in the boron neutron capture therapy (BNCT). The synthesis of rac-1-(9-o-Carboranyl)nonyl-2-methyl-glycero- 3-phosphocholine (B-Et-11-OMe) as a first representative is described. The carborane is introduced into the readily assembled glycerol ether moiety. The phosphocholine headgroup is introduced by 2-chloro-3-methyl-1,3,2-λ3-oxazaphospholane using a phosphoamidite strategy and subsequent ring opening under alkylating conditions.",

keywords = "BNCT, boron neutron capture therapy, ether lipid, glycidyl ether, phosphoamidite",

author = "Peter Lemmen and Birgit Werner",

note = "Funding Information: The expert technical assistance of Mrs. M. Koenig is gratefully acknowledged. We are indebted to Deutsche Forschungsgemeinschaft and Fonds der Chemischen Industrie for financial support and to the CEC for support of the 'European Collaboration on BNCT'.",

year = "1992",

month = sep,

doi = "10.1016/0009-3084(92)90096-8",

language = "English",

volume = "62",

pages = "185--191",

journal = "Chemistry and Physics of Lipids",

issn = "0009-3084",

publisher = "Elsevier Ireland Ltd",

number = "2",

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TY - JOUR

T1 - Synthesis of rac-1-(9-o-carboranyl)nonyl-2-methyl-glycero-3-phosphocholine (B-Et-11-OMe), a potential boron carrier for Boron Neutron Capture Therapy (BNCT)

AU - Lemmen, Peter

AU - Werner, Birgit

N1 - Funding Information: The expert technical assistance of Mrs. M. Koenig is gratefully acknowledged. We are indebted to Deutsche Forschungsgemeinschaft and Fonds der Chemischen Industrie for financial support and to the CEC for support of the 'European Collaboration on BNCT'.

PY - 1992/9

Y1 - 1992/9

N2 - Boron-containing analogues of ether lipids are proposed as boron carriers in the boron neutron capture therapy (BNCT). The synthesis of rac-1-(9-o-Carboranyl)nonyl-2-methyl-glycero- 3-phosphocholine (B-Et-11-OMe) as a first representative is described. The carborane is introduced into the readily assembled glycerol ether moiety. The phosphocholine headgroup is introduced by 2-chloro-3-methyl-1,3,2-λ3-oxazaphospholane using a phosphoamidite strategy and subsequent ring opening under alkylating conditions.

AB - Boron-containing analogues of ether lipids are proposed as boron carriers in the boron neutron capture therapy (BNCT). The synthesis of rac-1-(9-o-Carboranyl)nonyl-2-methyl-glycero- 3-phosphocholine (B-Et-11-OMe) as a first representative is described. The carborane is introduced into the readily assembled glycerol ether moiety. The phosphocholine headgroup is introduced by 2-chloro-3-methyl-1,3,2-λ3-oxazaphospholane using a phosphoamidite strategy and subsequent ring opening under alkylating conditions.

KW - BNCT

KW - boron neutron capture therapy

KW - ether lipid

KW - glycidyl ether

KW - phosphoamidite

UR - https://www.scopus.com/pages/publications/0026785232

U2 - 10.1016/0009-3084(92)90096-8

DO - 10.1016/0009-3084(92)90096-8

M3 - Article

AN - SCOPUS:0026785232

SN - 0009-3084

VL - 62

SP - 185

EP - 191

JO - Chemistry and Physics of Lipids

JF - Chemistry and Physics of Lipids

IS - 2

ER -

Synthesis of rac-1-(9-o-carboranyl)nonyl-2-methyl-glycero-3-phosphocholine (B-Et-11-OMe), a potential boron carrier for Boron Neutron Capture Therapy (BNCT)

Abstract

Keywords

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