A new procedure for the synthesis of azasugars

Luigi Lay; Francesco Nicotra; Angelo Paganini; Cristina Pangrazio; Luigi Panza

doi:10.1016/0040-4039(93)88084-V

A new procedure for the synthesis of azasugars

Luigi Lay, Francesco Nicotra, Angelo Paganini, Cristina Pangrazio, Luigi Panza

Risultato della ricerca: Contributo su rivista › Articolo in rivista › peer review

Abstract

Reaction of the commercially available 2,3,5-tri-O-benzyl-D-arabinose with a primary amine (RNH₂) affords the arabinofuranosylamine 2, which on treatment with a Grignard reagent stereoselectively gives the aminoalcohol 3. 3 is an useful precursor of azasugars: it is converted into the pyrrolidine 4 by treatment with Tf₂O-Py, whereas by oxidation with PCC it affords the lactam 5 which can be reduced to the corresponding amine 6.

Lingua originale	Inglese
pagine (da-a)	4555-4558
Numero di pagine	4
Rivista	Tetrahedron Letters
Volume	34
Numero di pubblicazione	28
DOI	https://doi.org/10.1016/0040-4039(93)88084-V
Stato di pubblicazione	Pubblicato - 9 lug 1993
Pubblicato esternamente	Sì

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title = "A new procedure for the synthesis of azasugars",

abstract = "Reaction of the commercially available 2,3,5-tri-O-benzyl-D-arabinose with a primary amine (RNH2) affords the arabinofuranosylamine 2, which on treatment with a Grignard reagent stereoselectively gives the aminoalcohol 3. 3 is an useful precursor of azasugars: it is converted into the pyrrolidine 4 by treatment with Tf2O-Py, whereas by oxidation with PCC it affords the lactam 5 which can be reduced to the corresponding amine 6.",

author = "Luigi Lay and Francesco Nicotra and Angelo Paganini and Cristina Pangrazio and Luigi Panza",

year = "1993",

month = jul,

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doi = "10.1016/0040-4039(93)88084-V",

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T1 - A new procedure for the synthesis of azasugars

AU - Lay, Luigi

AU - Nicotra, Francesco

AU - Paganini, Angelo

AU - Pangrazio, Cristina

AU - Panza, Luigi

PY - 1993/7/9

Y1 - 1993/7/9

N2 - Reaction of the commercially available 2,3,5-tri-O-benzyl-D-arabinose with a primary amine (RNH2) affords the arabinofuranosylamine 2, which on treatment with a Grignard reagent stereoselectively gives the aminoalcohol 3. 3 is an useful precursor of azasugars: it is converted into the pyrrolidine 4 by treatment with Tf2O-Py, whereas by oxidation with PCC it affords the lactam 5 which can be reduced to the corresponding amine 6.

AB - Reaction of the commercially available 2,3,5-tri-O-benzyl-D-arabinose with a primary amine (RNH2) affords the arabinofuranosylamine 2, which on treatment with a Grignard reagent stereoselectively gives the aminoalcohol 3. 3 is an useful precursor of azasugars: it is converted into the pyrrolidine 4 by treatment with Tf2O-Py, whereas by oxidation with PCC it affords the lactam 5 which can be reduced to the corresponding amine 6.

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U2 - 10.1016/0040-4039(93)88084-V

DO - 10.1016/0040-4039(93)88084-V

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 28

ER -

A new procedure for the synthesis of azasugars

Abstract

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