Convenient Syntheses of 3-Deoxy-D-manno-2-octulosonic Acid (KDO) and 3-Deoxy-D-glycero-D-galacto-2-nonulosonic Acid (KDN) Derivatives from D-Mannose
作者： Ken-ichi Sato , Tomoyuki Miyata , Ikuo Tanai , Yasuchika Yonezawa
DOI: 10.1246/CL.1994.129
关键词: Glycoside 、 Stereochemistry 、 2-Octulosonic acid 、 Chemistry 、 Wittig reaction 、 Aldose 、 Stereoselectivity 、 Mannose
摘要: Horner-Wittig reactions of 4-O-benzyl-2,3:5,6-di-O-isopropylidene-D-mannose and 2,3,4,5,6,7-hexa-O-benzyl-6-D-glycero-2,3,4,5-D-galacto-heptose with methyl 2-benzyloxycarbonylamino-2-(diethoxyphosphoryl)acetate gave the corresponding α-dehydroamino acid derivatives in good yields, respectively. They were converted to 3-deoxy-4,5:7,8-di-O-isopropylidene-α-D-manno-2-octulopyranosonate (methyl 3-deoxy-D-glycero-β-D-galacto-2-nonulopyranosid)onate via α-oxoalkanoate derivatives.
csj.jp参考文章(15)
CHUNGGI SHIN, YASUCHIKA YONEZAWA, TOYOFUMI YAMADA, Dehydrooligopeptides. V. Synthesis of N-Carboxy α-Dehydroamino Acid Anhydrides and Their Transformation to α-Dehydroamino Acid and Dehydrooligopeptide Derivatives Chemical & Pharmaceutical Bulletin. ,vol. 32, pp. 3934- 3944 ,(1984) , 10.1248/CPB.32.3934
D Nadano, M Iwasaki, S Endo, K Kitajima, S Inoue, Y Inoue, A naturally occurring deaminated neuraminic acid, 3-deoxy-D-glycero-D-galacto-nonulosonic acid (KDN). Its unique occurrence at the nonreducing ends of oligosialyl chains in polysialoglycoprotein of rainbow trout eggs. Journal of Biological Chemistry. ,vol. 261, pp. 11550- 11557 ,(1986) , 10.1016/S0021-9258(18)67278-3
Frank M. Unger, The Chemistry and Biological Significance of 3-Deoxy-d-manno-2-Octulosonic Acid (KDO) Advances in Carbohydrate Chemistry and Biochemistry Volume 38. ,vol. 38, pp. 323- 388 ,(1981) , 10.1016/S0065-2318(08)60313-3
Masahiro Imoto, Shoichi Kusomoto, Tetsu Shiba, A new synthesis of 3-deoxy-d-manno-2-octulosonic acid (kdo) from d-mannose Tetrahedron Letters. ,vol. 28, pp. 6235- 6238 ,(1987) , 10.1016/S0040-4039(00)61856-7
Masahiro Imoto, Naoto Kusunose, Yoshiki Matsuura, Shoichi Kusumoto, Tetsuo Shiba, Preparation of novel pyranosyl fluorides of 3-deoxy-D--2-octulosonic acid (KDO) feasible for synthesis of KDO α-glycosides Tetrahedron Letters. ,vol. 28, pp. 6277- 6280 ,(1987) , 10.1016/S0040-4039(01)91351-6
Ph. Coutrot, C. Grison, M. Tabyaoui, A new synthesis of 3-deoxy-d-manno-2-octulosonic acid (KDO) Tetrahedron Letters. ,vol. 34, pp. 5089- 5092 ,(1993) , 10.1016/S0040-4039(00)60683-4
P.A.M. van der Klein, G.J.P.H. Boons, G.H. Veeneman, G.A. van der Marel, J.H. van Boom, An efficient route to 3-deoxy-d-manno-2-octulosonic acid (KDO) derivatives via a 1,4-cyclic sulfate approach Tetrahedron Letters. ,vol. 30, pp. 5477- 5480 ,(1989) , 10.1016/S0040-4039(01)80598-0
Hans Poisel, α-Ketoester aus α-Aminosäureestern Chemische Berichte. ,vol. 111, pp. 3136- 3139 ,(1978) , 10.1002/CBER.19781110914
Ryuichi Shirai, Mitsunobu Nakamura, Sumiko Hara, Hiroaki Takayanagi, Haruo Ogura, Thermal rearrangement of N-acetyl-N-nitrosoneuraminic acid derivative: Synthesis of 3-deoxy-D-Nonulosonic acid (KDN) Tetrahedron Letters. ,vol. 29, pp. 4449- 4452 ,(1988) , 10.1016/S0040-4039(00)80519-5
Claudine Augé, Christine Gautheron, An efficient synthesis of cytidine monophospho-sialic acids with four immobilized enzymes. Tetrahedron Letters. ,vol. 29, pp. 789- 790 ,(1988) , 10.1016/S0040-4039(00)80210-5