A New Procedure for the Synthesis of Azasugars.

L Lay; F Nicotra; A Paganini; C Pangrazio; Luigi PANZA

A New Procedure for the Synthesis of Azasugars.

L Lay
, F Nicotra
, A Paganini
, C Pangrazio
, Luigi PANZA

Department of Pharmaceutical Sciences

Research output: Contribution to journal › Article

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.

Original language	English
Pages (from-to)	4555-4558
Number of pages	4
Journal	Tetrahedron Letters
Volume	34
Publication status	Published - 1993

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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 = "L Lay and F Nicotra and A Paganini and C Pangrazio and Luigi PANZA",

year = "1993",

language = "English",

volume = "34",

pages = "4555--4558",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Ltd.",

}

TY - JOUR

T1 - A New Procedure for the Synthesis of Azasugars.

AU - Lay, L

AU - Nicotra, F

AU - Paganini, A

AU - Pangrazio, C

AU - PANZA, Luigi

PY - 1993

Y1 - 1993

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.

UR - https://iris.uniupo.it/handle/11579/4468

M3 - Article

SN - 0040-4039

VL - 34

SP - 4555

EP - 4558

JO - Tetrahedron Letters

JF - Tetrahedron Letters

ER -

A New Procedure for the Synthesis of Azasugars.

Abstract

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