FORMYLATION OF PRIMARY HYDROXYL-GROUPS IN SUGARS

被引：18

作者：

GAN, LX

WHISTLER, RL

机构：

[1] PURDUE UNIV,WHISTLER CTR CARBOHYDRATE RES,W LAFAYETTE,IN 47907

[2] PURDUE UNIV,DEPT BIOCHEM,W LAFAYETTE,IN 47907

来源：

CARBOHYDRATE RESEARCH | 1990年 / 206卷 / 01期

关键词：

D O I：

10.1016/0008-6215(90)84006-G

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 99% formic acid at 25° formylates primary hydroxyl groups as shown by the easy formation of 6-O-formyl-d-glucopyranose and 6-O-formyl-d-fructofuranose, isolated as their tetra-acetates in yields of 77% and 31%, respectively. Likewise, d-glucitol gave the 2,3,4,5-tetra-O-acetyl-1,6-di-O-formyl derivative (84%) and methyl a-d-glucopyranoside gave the 6-formate (74%) characterized as the crystalline triacetate. On storage of the triacetate in methanol at 25°, the formyl group was lost and the 2,3,6-triacetate was formed, whereas the corresponding tribenzoate was deformylated in acidic methanol without migration of the benzoyl groups. © 1990.

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页码：65 / 69

页数：5

相关论文

共 10 条

[1] ACETYL MIGRATION IN PARTIALLY ACETYLATED D-GLUCOPYRANO-SIDES AND ACYLAMIDOHEXOPYRANOSIDES [J].

ALBERT, R ;

DAX, K ;

STUTZ, AE ;

WEIDMANN, H .

JOURNAL OF CARBOHYDRATE CHEMISTRY, 1983, 2 (03) :279-292

[2] SELECTIVE REMOVAL OF O-ACETYL GROUPS IN THE PRESENCE OF O-BENZOYL GROUPS BY ACID-CATALYZED METHANOLYSIS [J].

BYRAMOVA, NE ;

OVCHINNIKOV, MV ;

BACKINOWSKY, LV ;

KOCHETKOV, NK .

CARBOHYDRATE RESEARCH, 1983, 124 (01) :C8-C11

[3] A synthesis of conjugated bile acids I Glycocholic acid [J].

Cortese, F ;

Bauman, L .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1935, 57 :1393-1395

[4] SYNTHESES OF SOME FURANOSIDIC D-FRUCTOSE DERIVATIVES [J].

ERBING, B ;

LINDBERG, B .

ACTA CHEMICA SCANDINAVICA SERIES B-ORGANIC CHEMISTRY AND BIOCHEMISTRY, 1976, 30 (01) :12-14

[5] Action of formic acid on starch [J].

Gottlieb, D ;

Caldwell, CG ;

Hixon, RM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1940, 62 :3342-3344

[6] IMPROVED SPRAY REAGENT FOR THE DETECTION OF SUGARS [J].

MUKHERJEE, S ;

SRIVASTAVA, HC .

NATURE, 1952, 169 (4295) :330-330

[7] THE REACTION OF FORMIC ACID WITH CARBOHYDRATES .2. POLYSACCHARIDES - A NEW METHOD FOR DETERMINING ACCESSIBILITY [J].

TARKOW, H ;

STAMM, AJ .

JOURNAL OF PHYSICAL CHEMISTRY, 1952, 56 (02) :266-271

[8]

VIGNON MR, 1976, TETRAHEDRON LETT, P2445

[9] STARCH FORMATE [J].

WOLFF, IA ;

OLDS, DW ;

HILBERT, GE .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1957, 79 (14) :3860-3862

[10] PREPARATION AND METHANOLYSIS OF URIDINE, 6-AZAURIDINE AND 6-AZACYTIDINE O-FORMYL DERIVATIVES [J].

ZEMLICKA, J ;

BERANEK, J ;

SMRT, J .

COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS, 1962, 27 (12) :2784-&