Enantiospecific synthesis of a glycoside of D-epi-purpurosamine

2-Propyl D-epi-purpurosaminide dihydrochloride 14 and its di-N-acetylated derivative 15 were synthesized by an enantiospecific sequence which involves the 2-propyl 6-O-acetyl-3,4-dideoxy-α-D-erythro-hex-3-enopyranosid-2-ulose 2 as the key precursor. The first approach through the saturated diol 4, p...

Descripción completa

Guardado en:

Detalles Bibliográficos
Autores principales:	Iriarte Capaccio, Christian Ariel, Varela, Oscar José
Publicado:	2000
Materias:	2 propyl 2,6 diamino 2,3,4,6 tetradeoxy alpha dextro threo hexopyranoside 2 propyl 2,6 n,n diacetamido 2,3,4,6 tetradeoxy alpha dextro threo hexopyranoside alcohol allyl compound azide deoxysugar glycoside pyranoside toluenesulfonic acid derivative unclassified drug article chemical bond drug structure drug synthesis hydrogenation isomer priority journal reduction
Acceso en línea:	https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_09574166_v11_n24_p4945_IriarteCapaccio http://hdl.handle.net/20.500.12110/paper_09574166_v11_n24_p4945_IriarteCapaccio
Aporte de:	Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) de Universidad de Buenos Aires

id	paper:paper_09574166_v11_n24_p4945_IriarteCapaccio
record_format	dspace
spelling	paper:paper_09574166_v11_n24_p4945_IriarteCapaccio2023-06-08T15:56:27Z Enantiospecific synthesis of a glycoside of D-epi-purpurosamine Iriarte Capaccio, Christian Ariel Varela, Oscar José 2 propyl 2,6 diamino 2,3,4,6 tetradeoxy alpha dextro threo hexopyranoside 2 propyl 2,6 n,n diacetamido 2,3,4,6 tetradeoxy alpha dextro threo hexopyranoside alcohol allyl compound azide deoxysugar glycoside pyranoside toluenesulfonic acid derivative unclassified drug article chemical bond drug structure drug synthesis hydrogenation isomer priority journal reduction 2-Propyl D-epi-purpurosaminide dihydrochloride 14 and its di-N-acetylated derivative 15 were synthesized by an enantiospecific sequence which involves the 2-propyl 6-O-acetyl-3,4-dideoxy-α-D-erythro-hex-3-enopyranosid-2-ulose 2 as the key precursor. The first approach through the saturated diol 4, prepared by reduction of the enone system of 2, was unsuccessful as the C-2 position of 2,6-di-O-sulfonyl derivatives 5 and 6 resisted substitution by azide. Therefore, an alternative sequence starting from the allylic alcohol 3, also derived from 2, was developed. In this case, the 2,6-di-O-tosyl derivative 9 gave the expected 2,6-diazide 10 with additional unwanted rearrangement of the double bond to the 2-propyl 4,6-diazido-2,3,4,6-tetradeoxy-α-D-threo-hex-2-enopyranoside 11 isomer. However, the ditriflate derivative 13, analogous to 9, underwent substitution to afford the diazide 10 in good yield. Upon reduction of the azide functions and saturation of the double bond of 10 by catalytic hydrogenation under acidic conditions, the dihydrochloride salt 14 was obtained as a crystalline product (43% overall yield from 3. © 2001 Elsevier Science Ltd. Fil:Iriarte Capaccio, C.A. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Varela, O. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. 2000 https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_09574166_v11_n24_p4945_IriarteCapaccio http://hdl.handle.net/20.500.12110/paper_09574166_v11_n24_p4945_IriarteCapaccio
institution	Universidad de Buenos Aires
institution_str	I-28
repository_str	R-134
collection	Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA)
topic	2 propyl 2,6 diamino 2,3,4,6 tetradeoxy alpha dextro threo hexopyranoside 2 propyl 2,6 n,n diacetamido 2,3,4,6 tetradeoxy alpha dextro threo hexopyranoside alcohol allyl compound azide deoxysugar glycoside pyranoside toluenesulfonic acid derivative unclassified drug article chemical bond drug structure drug synthesis hydrogenation isomer priority journal reduction
spellingShingle	2 propyl 2,6 diamino 2,3,4,6 tetradeoxy alpha dextro threo hexopyranoside 2 propyl 2,6 n,n diacetamido 2,3,4,6 tetradeoxy alpha dextro threo hexopyranoside alcohol allyl compound azide deoxysugar glycoside pyranoside toluenesulfonic acid derivative unclassified drug article chemical bond drug structure drug synthesis hydrogenation isomer priority journal reduction Iriarte Capaccio, Christian Ariel Varela, Oscar José Enantiospecific synthesis of a glycoside of D-epi-purpurosamine
topic_facet	2 propyl 2,6 diamino 2,3,4,6 tetradeoxy alpha dextro threo hexopyranoside 2 propyl 2,6 n,n diacetamido 2,3,4,6 tetradeoxy alpha dextro threo hexopyranoside alcohol allyl compound azide deoxysugar glycoside pyranoside toluenesulfonic acid derivative unclassified drug article chemical bond drug structure drug synthesis hydrogenation isomer priority journal reduction
description	2-Propyl D-epi-purpurosaminide dihydrochloride 14 and its di-N-acetylated derivative 15 were synthesized by an enantiospecific sequence which involves the 2-propyl 6-O-acetyl-3,4-dideoxy-α-D-erythro-hex-3-enopyranosid-2-ulose 2 as the key precursor. The first approach through the saturated diol 4, prepared by reduction of the enone system of 2, was unsuccessful as the C-2 position of 2,6-di-O-sulfonyl derivatives 5 and 6 resisted substitution by azide. Therefore, an alternative sequence starting from the allylic alcohol 3, also derived from 2, was developed. In this case, the 2,6-di-O-tosyl derivative 9 gave the expected 2,6-diazide 10 with additional unwanted rearrangement of the double bond to the 2-propyl 4,6-diazido-2,3,4,6-tetradeoxy-α-D-threo-hex-2-enopyranoside 11 isomer. However, the ditriflate derivative 13, analogous to 9, underwent substitution to afford the diazide 10 in good yield. Upon reduction of the azide functions and saturation of the double bond of 10 by catalytic hydrogenation under acidic conditions, the dihydrochloride salt 14 was obtained as a crystalline product (43% overall yield from 3. © 2001 Elsevier Science Ltd.
author	Iriarte Capaccio, Christian Ariel Varela, Oscar José
author_facet	Iriarte Capaccio, Christian Ariel Varela, Oscar José
author_sort	Iriarte Capaccio, Christian Ariel
title	Enantiospecific synthesis of a glycoside of D-epi-purpurosamine
title_short	Enantiospecific synthesis of a glycoside of D-epi-purpurosamine
title_full	Enantiospecific synthesis of a glycoside of D-epi-purpurosamine
title_fullStr	Enantiospecific synthesis of a glycoside of D-epi-purpurosamine
title_full_unstemmed	Enantiospecific synthesis of a glycoside of D-epi-purpurosamine
title_sort	enantiospecific synthesis of a glycoside of d-epi-purpurosamine
publishDate	2000
url	https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_09574166_v11_n24_p4945_IriarteCapaccio http://hdl.handle.net/20.500.12110/paper_09574166_v11_n24_p4945_IriarteCapaccio
work_keys_str_mv	AT iriartecapacciochristianariel enantiospecificsynthesisofaglycosideofdepipurpurosamine AT varelaoscarjose enantiospecificsynthesisofaglycosideofdepipurpurosamine
_version_	1768546031426863104

Enantiospecific synthesis of a glycoside of D-epi-purpurosamine

Ejemplares similares