A NEW PROCEDURE FOR THE SYNTHESIS OF AZASUGARS

被引：54

作者：

LAY, L ^{[1
]}

NICOTRA, F ^{[1
]}

PAGANINI, A ^{[1
]}

PANGRAZIO, C ^{[1
]}

PANZA, L ^{[1
]}

机构：

[1] CNR,CTR STUDIO SOSTANZE ORGAN NAT,DIPARTIMENTO CHIM ORGAN & IND,I-20133 MILAN,ITALY

来源：

TETRAHEDRON LETTERS | 1993年 / 34卷 / 28期

关键词：

D O I：

10.1016/0040-4039(93)88084-V

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

引用

页码：4555 / 4558

页数：4

共 50 条

[31] A new procedure for the synthesis of lithium hexafluorophosphate
Naejus, R
Lemordant, D
Coudert, R
Willmann, P
JOURNAL OF FLUORINE CHEMISTRY, 1998, 90 (01) : 81 - 85
[32] A NEW PROCEDURE FOR THE SYNTHESIS OF ALKYL PERFLUOROALKANEDITHIOCARBOXYLATES
SHERMOLOVICH, YG
SLUSARENKO, YI
TIMOSHENKO, VM
ROZHENKO, AB
MARKOVSKI, LN
JOURNAL OF FLUORINE CHEMISTRY, 1991, 55 (03) : 329 - 333
[33] A new procedure for synthesis of phosphorylated ynamines
Svintsitskaya, N. I.
Aleksandrova, A. V.
Dogadina, A. V.
Ionin, B. I.
RUSSIAN JOURNAL OF GENERAL CHEMISTRY, 2008, 78 (01) : 157 - 159
[34] NEW PROCEDURE FOR THE TOTAL SYNTHESIS OF CILOSTAMIDE
Seyedi, Seyed Mohammad
Sadeghian, Hamid
Arghiani, Zahra
HETEROCYCLIC COMMUNICATIONS, 2008, 14 (03) : 183 - 186
[35] A new procedure for synthesis of phosphorylated ynamines
N. I. Svintsitskaya
A. V. Aleksandrova
A. V. Dogadina
B. I. Ionin
Russian Journal of General Chemistry, 2008, 78 : 157 - 159
[36] Synthesis of azasugars. Unexpected results in the oxidative cyclization of aminoalditols
Cipolla, L
Nicotra, F
Pangrazio, C
GAZZETTA CHIMICA ITALIANA, 1996, 126 (10): : 663 - 666
[37] Synthesis of (difluoromethyl)phosphonate azasugars designed as inhibitors for glycosyl transferases
Behr, JB
Evina, CM
Phung, N
Guillerm, G
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1997, (11): : 1597 - 1599
[38] New, efficient routes to aminosugars and azasugars, end their derivatives.
Wang, T
Lin, SN
Wu, XY
Geng, XD
Ojima, I
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1999, 218 : U129 - U129
[39] Biosynthesis of azasugars
Clark, Lorraine
Horenstein, Nicole
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2010, 240
[40] Ring-closing metathesis mediated synthesis of pyrrolizidine and quinolizidine azasugars
Overkleeft, HS
Bruggeman, P
Pandit, UK
TETRAHEDRON LETTERS, 1998, 39 (22) : 3869 - 3872

← 1 2 3 4 5 →