CHEMISTRY OF N,P-ACETALS - APPLICATION TO THE SYNTHESIS OF 20-KETOSTEROIDS

J STOELWINDER; WJ VANZOEST; A.M. van Leusen

CHEMISTRY OF N,P-ACETALS - APPLICATION TO THE SYNTHESIS OF 20-KETOSTEROIDS

J STOELWINDER
, WJ VANZOEST
, A.M. van Leusen

Bio-organic Chemistry

Onderzoeksoutput › Academic › peer review

13 Citaten (Scopus)

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A series of new derivatives of alpha-(isocyanomethyl)phosphonates (6a,b,c and 9) is described, which are formed by methylation of (E)-17-[(diethylphosphono)isocyanomethylene] steroids 5a,b,c and 17-beta-[(diethylphosphono)isocyanomethyl] steroid 8. It proved possible to hydrolyze these compounds under relatively mild conditions to 20-ketosteroids 7a,b,c and 10, showing for the first time that geminal N- and P-substituted carbon compounds do react as N,P-acetals.

Originele taal-2	English
Pagina's (van-tot)	2249-2252
Aantal pagina's	4
Tijdschrift	Journal of Organic Chemistry
Volume	57
Nummer van het tijdschrift	8
Status	Published - 10-apr-1992

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@article{47c4d76ceb78423cabda0e3ca9149f7e,

title = "CHEMISTRY OF N,P-ACETALS - APPLICATION TO THE SYNTHESIS OF 20-KETOSTEROIDS",

abstract = "A series of new derivatives of alpha-(isocyanomethyl)phosphonates (6a,b,c and 9) is described, which are formed by methylation of (E)-17-[(diethylphosphono)isocyanomethylene] steroids 5a,b,c and 17-beta-[(diethylphosphono)isocyanomethyl] steroid 8. It proved possible to hydrolyze these compounds under relatively mild conditions to 20-ketosteroids 7a,b,c and 10, showing for the first time that geminal N- and P-substituted carbon compounds do react as N,P-acetals.",

keywords = "PHOSPHORUS ANALOGS, CARBONYL-COMPOUNDS, AMINO-ACIDS, DERIVATIVES, ISOCYANIDES, PEPTIDES, CHAIN",

author = "J STOELWINDER and WJ VANZOEST and \{van Leusen\}, A.M.",

year = "1992",

month = apr,

day = "10",

language = "English",

volume = "57",

pages = "2249--2252",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "AMER CHEMICAL SOC INC",

number = "8",

}

TY - JOUR

T1 - CHEMISTRY OF N,P-ACETALS - APPLICATION TO THE SYNTHESIS OF 20-KETOSTEROIDS

AU - STOELWINDER, J

AU - VANZOEST, WJ

AU - van Leusen, A.M.

PY - 1992/4/10

Y1 - 1992/4/10

N2 - A series of new derivatives of alpha-(isocyanomethyl)phosphonates (6a,b,c and 9) is described, which are formed by methylation of (E)-17-[(diethylphosphono)isocyanomethylene] steroids 5a,b,c and 17-beta-[(diethylphosphono)isocyanomethyl] steroid 8. It proved possible to hydrolyze these compounds under relatively mild conditions to 20-ketosteroids 7a,b,c and 10, showing for the first time that geminal N- and P-substituted carbon compounds do react as N,P-acetals.

AB - A series of new derivatives of alpha-(isocyanomethyl)phosphonates (6a,b,c and 9) is described, which are formed by methylation of (E)-17-[(diethylphosphono)isocyanomethylene] steroids 5a,b,c and 17-beta-[(diethylphosphono)isocyanomethyl] steroid 8. It proved possible to hydrolyze these compounds under relatively mild conditions to 20-ketosteroids 7a,b,c and 10, showing for the first time that geminal N- and P-substituted carbon compounds do react as N,P-acetals.

KW - PHOSPHORUS ANALOGS

KW - CARBONYL-COMPOUNDS

KW - AMINO-ACIDS

KW - DERIVATIVES

KW - ISOCYANIDES

KW - PEPTIDES

KW - CHAIN

M3 - Article

SN - 0022-3263

VL - 57

SP - 2249

EP - 2252

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 8

ER -

CHEMISTRY OF N,P-ACETALS - APPLICATION TO THE SYNTHESIS OF 20-KETOSTEROIDS

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