Desulfonylation with Mg-MeOH-NiBr2:: An expedient reagent system for the synthesis of 2-amino-2,3-dideoxy furanosides

被引：28

作者：

Das, I ^{[1
]}

Pathak, T ^{[1
]}

机构：

[1] Indian Inst Technol, Dept Chem, Kharagpur 721302, W Bengal, India

来源：

ORGANIC LETTERS | 2006年 / 8卷 / 07期

关键词：

D O I：

10.1021/ol053082a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A catalytic amount of NiBr2 with Mg-MeOH increases the efficiency of reductive desulfonylation of the beta-sulfonylated aminosugars. The Mg-MeOH-NiBr2 system has been utilized in the synthesis of 2-amino-2,3-dideoxypentofuranosides and 2-amino-2,3-dideoxyhexofuranosides. The yield of the desulfonylation improved dramatically from 0% with the known reagents to 44-75% with Mg-MeOH-NiBr2.

引用

页码：1303 / 1306

页数：4

共 24 条

[1] Asymmetric synthesis of functionalized piperidine derivatives:: synthesis of (S)-anatabine
Balasubramanian, T
Hassner, A
[J]. TETRAHEDRON-ASYMMETRY, 1998, 9 (13) : 2201 - 2205
[2] 2-deoxystreptamine: Central scaffold of aminoglycoside antibiotics
Busscher, GF
Rutjes, FPJT
van Delft, FL
[J]. CHEMICAL REVIEWS, 2005, 105 (03) : 775 - 791
[3] TRANSITION-METAL-PROMOTED REACTIONS NICKELOCENE-LITHIUM ALUMINUM-HYDRIDE .19. A VERSATILE DESULFURIZATION REAGENT
CHAN, MC
CHENG, KM
HO, KM
NG, CT
YAM, TM
WANG, BSL
LUH, TY
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (19) : 4466 - 4471
[4] EIJI A, 1996, SYNLETT, P100
[5] François D, 1998, ANGEW CHEM INT EDIT, V37, P104, DOI 10.1002/(SICI)1521-3773(19980202)37:1/2<104::AID-ANIE104>3.0.CO
[6] 2-K
[7] GAMBLE MP, 1995, SYNLETT, P779
[8] Giblin GMP, 1997, SYNLETT, P589
[9] TRANSITION-METAL PROMOTED REACTIONS .27. NICKEL(II) LITHIUM ALUMINUM-HYDRIDE MEDIATED REDUCTION OF CARBON SULFUR BONDS
HO, KM
LAM, CH
LUH, TY
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (18) : 4474 - 4476
[10] Molecular targets for design of novel inhibitors to circumvent aminoglycoside resistance
Jana, S
Deb, JK
[J]. CURRENT DRUG TARGETS, 2005, 6 (03) : 353 - 361

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