Hydroxylated pyrrolidines. Synthesis of 1,4-dideoxy-1,4-imino-L-lyxitol, 1,4,5-trideoxy-1,4-imino-D- and -L-lyxo-hexitol, 2,3,6-trideoxy-3,6-imino-D-glycero-L-altro- and -D-glycero-L-galacto-octitols, and of a chiral potential precursor of carbapenem systems

D. K. Thompson; C. N. Hubert; R. H. Wightman

doi:10.1016/S0040-4020(01)90234-0

Hydroxylated pyrrolidines. Synthesis of 1,4-dideoxy-1,4-imino-L-lyxitol, 1,4,5-trideoxy-1,4-imino-D- and -L-lyxo-hexitol, 2,3,6-trideoxy-3,6-imino-D-glycero-L-altro- and -D-glycero-L-galacto-octitols, and of a chiral potential precursor of carbapenem systems

D. K. Thompson, C. N. Hubert, R. H. Wightman

School of Engineering & Physical Sciences

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

96 Citations (Scopus)

Abstract

Enantiospecific syntheses are reported for the title pyrrolidines, from carbohydrate precursors. An intermediate in one of the routes, ethyl 2,3,6-trideoxy-3,6-imino-4,5:7,8-di-O-isopropylidine-D-glycero-L-altr o-octonate (23), could be converted in two steps into a ß-lactam.

Original language	English
Pages (from-to)	3827-3840
Number of pages	14
Journal	Tetrahedron
Volume	49
Issue number	18
DOIs	https://doi.org/10.1016/S0040-4020(01)90234-0
Publication status	Published - 1993

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Thompson, D. K., Hubert, C. N., & Wightman, R. H. (1993). Hydroxylated pyrrolidines. Synthesis of 1,4-dideoxy-1,4-imino-L-lyxitol, 1,4,5-trideoxy-1,4-imino-D- and -L-lyxo-hexitol, 2,3,6-trideoxy-3,6-imino-D-glycero-L-altro- and -D-glycero-L-galacto-octitols, and of a chiral potential precursor of carbapenem systems. Tetrahedron, 49(18), 3827-3840. https://doi.org/10.1016/S0040-4020(01)90234-0

@article{36bc1cbe61474908b4051a33197949e1,

title = "Hydroxylated pyrrolidines. Synthesis of 1,4-dideoxy-1,4-imino-L-lyxitol, 1,4,5-trideoxy-1,4-imino-D- and -L-lyxo-hexitol, 2,3,6-trideoxy-3,6-imino-D-glycero-L-altro- and -D-glycero-L-galacto-octitols, and of a chiral potential precursor of carbapenem systems",

abstract = "Enantiospecific syntheses are reported for the title pyrrolidines, from carbohydrate precursors. An intermediate in one of the routes, ethyl 2,3,6-trideoxy-3,6-imino-4,5:7,8-di-O-isopropylidine-D-glycero-L-altr o-octonate (23), could be converted in two steps into a {\ss}-lactam.",

author = "Thompson, {D. K.} and Hubert, {C. N.} and Wightman, {R. H.}",

year = "1993",

doi = "10.1016/S0040-4020(01)90234-0",

language = "English",

volume = "49",

pages = "3827--3840",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Elsevier",

number = "18",

}

Thompson, DK, Hubert, CN & Wightman, RH 1993, 'Hydroxylated pyrrolidines. Synthesis of 1,4-dideoxy-1,4-imino-L-lyxitol, 1,4,5-trideoxy-1,4-imino-D- and -L-lyxo-hexitol, 2,3,6-trideoxy-3,6-imino-D-glycero-L-altro- and -D-glycero-L-galacto-octitols, and of a chiral potential precursor of carbapenem systems', Tetrahedron, vol. 49, no. 18, pp. 3827-3840. https://doi.org/10.1016/S0040-4020(01)90234-0

Hydroxylated pyrrolidines. Synthesis of 1,4-dideoxy-1,4-imino-L-lyxitol, 1,4,5-trideoxy-1,4-imino-D- and -L-lyxo-hexitol, 2,3,6-trideoxy-3,6-imino-D-glycero-L-altro- and -D-glycero-L-galacto-octitols, and of a chiral potential precursor of carbapenem systems. / Thompson, D. K.; Hubert, C. N.; Wightman, R. H.

In: Tetrahedron, Vol. 49, No. 18, 1993, p. 3827-3840.

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

TY - JOUR

T1 - Hydroxylated pyrrolidines. Synthesis of 1,4-dideoxy-1,4-imino-L-lyxitol, 1,4,5-trideoxy-1,4-imino-D- and -L-lyxo-hexitol, 2,3,6-trideoxy-3,6-imino-D-glycero-L-altro- and -D-glycero-L-galacto-octitols, and of a chiral potential precursor of carbapenem systems

AU - Thompson, D. K.

AU - Hubert, C. N.

AU - Wightman, R. H.

PY - 1993

Y1 - 1993

N2 - Enantiospecific syntheses are reported for the title pyrrolidines, from carbohydrate precursors. An intermediate in one of the routes, ethyl 2,3,6-trideoxy-3,6-imino-4,5:7,8-di-O-isopropylidine-D-glycero-L-altr o-octonate (23), could be converted in two steps into a ß-lactam.

AB - Enantiospecific syntheses are reported for the title pyrrolidines, from carbohydrate precursors. An intermediate in one of the routes, ethyl 2,3,6-trideoxy-3,6-imino-4,5:7,8-di-O-isopropylidine-D-glycero-L-altr o-octonate (23), could be converted in two steps into a ß-lactam.

U2 - 10.1016/S0040-4020(01)90234-0

DO - 10.1016/S0040-4020(01)90234-0

M3 - Article

SN - 0040-4020

VL - 49

SP - 3827

EP - 3840

JO - Tetrahedron

JF - Tetrahedron

IS - 18

ER -