methyl (methyl 5-acetamido-3,4,5-trideoxy-4-C-methyl-8,9-O(methylethylidene)-β-D-glycero-D-galacto-2-nonulopyranosid)onate | 130264-74-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl (methyl 5-acetamido-3,4,5-trideoxy-4-C-methyl-8,9-O(methylethylidene)-β-D-glycero-D-galacto-2-nonulopyranosid)onate
• 英文别名: methyl (2S,4S,5R,6R)-5-acetamido-6-[(S)-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-hydroxymethyl]-2-methoxy-4-methyloxane-2-carboxylate
• CAS: 130264-74-3
• 化学式: C₁₇H₂₉NO₈
• 分子量: 375.419
• InChiKey: DJVDEHYZCOJRCX-DFLOEGRMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  113
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  methyl (methyl 5-acetamido-3,4,5-trideoxy-4-C-methyl-8,9-O(methylethylidene)-β-D-glycero-D-galacto-2-nonulopyranosid)onate 在 盐酸 、 sodium hydroxide 、 Amberlyst 15H⁺ 作用下， 生成 5-acetamido-3,4,5-trideoxy-D-glycero-D-galacto-2-nonulosonic acid
  参考文献：
  名称：

  Structural variations of N-acetylneuraminic acid, part 19: Synthesis of both epimeric pairs of the 4-C-methyl- and 4-deoxy-4-C-methyl- as well as of the ?-methylketoside of 4-deoxy-4-C-methylene-N-acetylneuraminic acid

  摘要：

  While the reaction of the 4-oxo-Neu 5 Ac derivative 2a with tributoxy methyl zirconate led exclusively to equatorial 4-C-methyl derivative 3a, the analogous reaction with tetramethyl zirconate yielded a 3:2 mixture of both diastereoisomers 3a and 4a. After removal of protecting groups the 5-acetamido-3,4-dideoxy-4-C-methyl-D-glycero-D-galacto-2-nonulosoic acid 5a and 5-acetamido-3,4-dideoxy-4-C-methyl-D-glycero-D-talo-2-nonulosonic acid 6 a were obtained. The 4-C-methylene derivative was prepared by treatment of the same 4-oxo-derivative with CH2I2/Zn/Cp2ZrCl2. Subsequent hydrogenation led to both epimeric 4-deoxy-4-C-methyl derivatives 8a and 9a. Final removal of protecting groups gave the 5-acetamido-3,4,5-trideoxy-4-C-methyl-D-glycero-D-galacto-2-nonulosonic acid 10a respectively the 5-acetamido-2,7-anhydro-4-C-methyl-3,4,5-trideoxy-D-glycero-D-talo-2-nonulosonic acid 11a. The beta-methylketosides of the 4-deoxy-4-C-methyl- (16) and 4-C-methylene-Neu 5 Ac (15) were prepared via the peracetylated derivatives to obtain modell substrates for enzymatic studies. Thus all free acids were tested for inhibition of CMP-sialate synthase. Only the 4-C-methylene compound 15 showed most unexpectedly a strong competitive inhibition of this enzyme.

  DOI：

  10.1007/bf00815172
• 作为产物：
  描述：

  methyl-5-acetamido-8,9-O-(1'-methyl-ethylidene)-3,5-dideoxy-β-D-manno-2,4-nonodiulopyranosidonic acid methyl ester 在 palladium on activated charcoal 二氯二茂锆 、 氢气 、 锌 作用下， 以 丙酮 为溶剂， 反应 0.38h， 生成 methyl (methyl 5-acetamido-3,4,5-trideoxy-4-C-methyl-8,9-O(methylethylidene)-β-D-glycero-D-galacto-2-nonulopyranosid)onate
  参考文献：
  名称：

  Structural variations of N-acetylneuraminic acid, part 19: Synthesis of both epimeric pairs of the 4-C-methyl- and 4-deoxy-4-C-methyl- as well as of the ?-methylketoside of 4-deoxy-4-C-methylene-N-acetylneuraminic acid

  摘要：

  While the reaction of the 4-oxo-Neu 5 Ac derivative 2a with tributoxy methyl zirconate led exclusively to equatorial 4-C-methyl derivative 3a, the analogous reaction with tetramethyl zirconate yielded a 3:2 mixture of both diastereoisomers 3a and 4a. After removal of protecting groups the 5-acetamido-3,4-dideoxy-4-C-methyl-D-glycero-D-galacto-2-nonulosoic acid 5a and 5-acetamido-3,4-dideoxy-4-C-methyl-D-glycero-D-talo-2-nonulosonic acid 6 a were obtained. The 4-C-methylene derivative was prepared by treatment of the same 4-oxo-derivative with CH2I2/Zn/Cp2ZrCl2. Subsequent hydrogenation led to both epimeric 4-deoxy-4-C-methyl derivatives 8a and 9a. Final removal of protecting groups gave the 5-acetamido-3,4,5-trideoxy-4-C-methyl-D-glycero-D-galacto-2-nonulosonic acid 10a respectively the 5-acetamido-2,7-anhydro-4-C-methyl-3,4,5-trideoxy-D-glycero-D-talo-2-nonulosonic acid 11a. The beta-methylketosides of the 4-deoxy-4-C-methyl- (16) and 4-C-methylene-Neu 5 Ac (15) were prepared via the peracetylated derivatives to obtain modell substrates for enzymatic studies. Thus all free acids were tested for inhibition of CMP-sialate synthase. Only the 4-C-methylene compound 15 showed most unexpectedly a strong competitive inhibition of this enzyme.

  DOI：

  10.1007/bf00815172

文献信息

• A facile and direct entry to functionalised Neu5Ac2En derivatives from the methyl ketoside of Neu5Ac methyl esters
  作者：Gaik B. Kok、Darrin R. Groves、Mark von Itzstein

  DOI：10.1039/cc9960002017

  日期：——

  Acetolysis of some methyl ketosides of N-acetylneuraminic acid (Neu5Ac) methyl esters, in a one-pot reaction, provides a rapid and efficient access to the corresponding 2,3-unsaturated Neu5Ac (Neu5Ac2en) derivatives.

  通过对 N-乙酰神经氨酸（Neu5Ac）甲酯的一些甲基酮苷进行乙酰分解的单锅反应，可以快速有效地获得相应的 2,3-不饱和 Neu5Ac（Neu5Ac2en）衍生物。
• Kok, Gaik B.; Groves, Darrin; Von Itzstein, Mark, Journal of the Chemical Society. Perkin transactions I, 1999, # 15, p. 2109 - 2115
  作者：Kok, Gaik B.、Groves, Darrin、Von Itzstein, Mark

  DOI：——

  日期：——
• Synthesis of the epimeric pair of 4-deoxy-4-(R)- and 4-deoxy-4-(S)-C-methyl-n-acetylneuraminic acid
  作者：Michael Hartmann、Erich Zbiral

  DOI：10.1016/0040-4039(90)80171-h

  日期：1990.1