FORMATION OF AN UNSATURATED HEPTONIC ACID DURING WOLFF REARRANGEMENT OF 1-DEOXY-1-DIAZO-D-GLUCO-HEPTULOSE PENTAACETATE

被引：8

作者：

CHARON, D

机构：

[1] Institut de Biochimie, Faculté des Sciences, Orsay

来源：

CARBOHYDRATE RESEARCH | 1969年 / 11卷 / 04期

关键词：

D O I：

10.1016/S0008-6215(00)81253-7

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

Application of the Wolff rearrangement to an acetylated α-diazoketone (3,4,5,6,7-penta-O-acetyl-1-deoxy-1-diazo-d-gluco-heptulose), using silver oxide as catalyst, gave an α,β-unsaturated acid (trans-4,5,6,7-tetra-O-acetyl-2,3-dideoxy-d-arabino-hept-2-enonic acid) in good yield, instead of the expected, saturated β-acetoxy acid. The structure of this new compound, established by spectroscopic data, was confirmed by degradation studies. © 1969.

引用

页码：447 / &

共 12 条

[1] Action of the transfer of carbon acids in their high homogenous respectively its derivative
Arndt, F
Eisert, B
[J]. BERICHTE DER DEUTSCHEN CHEMISCHEN GESELLSCHAFT, 1935, 68 : 200 - 208
[2] BACHELOR FW, 1967, TETRAHEDRON LETT, P4333
[3] BESTMANN HJ, 1961, BER, V94, P751
[4] The acetyl derivatives of gluconic and xylonic acids
Major, RT
Cook, EW
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1936, 58 : 2474 - 2477
[5] RAO CNR, 1964, CHEMICAL APPLICATION, P232
[6] RAO CNR, 1964, CHEMICAL APPLICATION, P147
[7] SILVERSTEIN RM, SPECTROMETRIC IDENTI, P138
[8] SILVERSTEIN RM, SPECTROMETRIC IDENTI, P162
[9] SMITH PAS, 1967, MOL REARRANGEMENTS 1, P528
[10] Wolff L., 1912, LIEBIGS ANN CHEM, V394, P23

← 1 2 →