methyl (methyl 5-acetamido-3,5-dideoxy-8,9-O-isopropylidene-D-glycero-α-D-galacto-2-nonulopyrasidonate) | 110390-89-1

• 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-3,5-dideoxy-8,9-O-isopropylidene-D-glycero-α-D-galacto-2-nonulopyrasidonate)
• 英文别名: Methyl-(methyl-5-acetamido-3,5-dideoxy-8,9-O-methylethyliden-D-glycero-α-D-galacto-nonulopyranosid)onat；methyl (methyl 5-acetamido-3,5-dideoxy-8,9-O-isopropylidene-α-D-glycero-D-galacto-2-nonulopyranosid)onate；methyl (2R,4S,5R,6R)-5-acetamido-6-[(S)-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-hydroxymethyl]-4-hydroxy-2-methoxyoxane-2-carboxylate
• CAS: 110390-89-1
• 化学式: C₁₆H₂₇NO₉
• 分子量: 377.392
• InChiKey: MSEJSFGFCUHMFH-ZIVBLGBNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 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：
  133
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  methyl (methyl 5-acetamido-3,5-dideoxy-8,9-O-isopropylidene-D-glycero-α-D-galacto-2-nonulopyrasidonate) 生成 methyl (2R,4S,5S,6R)-5-acetamido-4-[tert-butyl(dimethyl)silyl]oxy-6-[(S)-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-hydroxymethyl]-2-methoxyoxane-2-carboxylate
  参考文献：
  名称：

  ANAZAWA, KATSUKO;FURUHATA, KIMIO;OGURA, HARUO, CHEM. AND PHARM. BULL., 36,(1988) N2, C. 4976-4979

  摘要：

  DOI：
• 作为产物：
  描述：

  methyl (methyl 5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosid)onate 生成 methyl (methyl 5-acetamido-3,5-dideoxy-8,9-O-isopropylidene-D-glycero-α-D-galacto-2-nonulopyrasidonate)
  参考文献：
  名称：

  ANAZAWA, KATSUKO;FURUHATA, KIMIO;OGURA, HARUO, CHEM. AND PHARM. BULL., 36,(1988) N2, C. 4976-4979

  摘要：

  DOI：

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。
• ANAZAWA, KATSUKO;FURUHATA, KIMIO;OGURA, HARUO, CHEM. AND PHARM. BULL., 36,(1988) N2, C. 4976-4979
  作者：ANAZAWA, KATSUKO、FURUHATA, KIMIO、OGURA, HARUO

  DOI：——

  日期：——
• Strukturelle Abwandlungen an N-Acetylneuramins�ure, 25. Mitt.: Synthese von Methyl-2-?-glycosiden von 4-epi-, 7-epi-, 8-epi- und 7,8-bis-epi-N-Acetylneuramins�ure
  作者：B. P. Bandgar、E. Zbiral

  DOI：10.1007/bf00811116

  日期：1991.12

  The alpha-methylketoside of N-acetylneuraminic acid methylester (4) is transformed via the deacetylated compound 5 into the 9,8-O-isopropylidenderivative 6 which could be oxidized regioselectivity by RuO4 to the corresponding 4-oxo-sialic acid analogue 7. Reduction with the borane-ammonia complex produces a 1:1 mixture of 6 and the desired alpha-methylketoside of 9,8-O-isopropyliden-4-epi-N-acetyl-neuraminic acid methylester (8). Removing of the isopropylidene group gives the alpha-methylketoside of 4-epi-N-acetylneuraminic acid alpha-methylketoside (10). On the other hand compound 5 was turned into the 4,8,9-tri-O-t-butyldimethylsilylderivative 11 a from which the corresponding 7-oxo-compound 12 by oxidation with RuO4 derives. The reduction of 12 with BH3 - NH3 yielded a 1:1 mixture of the starting material 11 a and the desired 7-epi-derivative 13 a which gives either via the purified peracetylated alpha-methylketosid of 7-epi-N-acetylneuraminic acid methylester (14) or a direct saponification the sodium salt of 7-epi-N-acetylneuraminic acid-alpha-methylketoside (15).Applying the Konigs-Knorr procedure to the peracetylated 8-epi-N-acetylneuraminic acid methylester (16) gives rise to the formation of a 1:1 mixture of the corresponding alpha- and beta-methylketosides 17 and 18 besides traces of the corresponding 2,3-dideoxy-2,3-dideohydro-sialic acid derivative 19. After chromatographic separation of 17 further saponification leads to the sodium salt of 8-epi-N-acetylneuraminic acid-alpha-methylketoside (20). In an analogous procedure the sodium salt of 7,8-di-epi-N-acetylneuraminic acid-alpha-methylketoside (25) was prepared starting from the peracetylated 7,8-di-epi-N-acetylneuraminic acid methylester (21), whereby a mixture of the alpha- and beta-methylketosides 22 and 23 was formed in a ratio 95:5 besides traces of the peracetylated 2,3-dideoxy-2,3-didehydrosialic acid methylester (24).
• Synthesis and Biological Properties ofN-Acetyl-4-deoxy-D-neuraminic Acid
  作者：Heinz-Werner Hagedorn、Reinhard Brossmer

  DOI：10.1002/hlca.19860690837

  日期：1986.12.10

  AbstractN‐Acetylneuraminic acid (1) can be transformed into the methyl α‐D‐ketoside 2 which, by reaction with methanesulfonyl chloride, yields the corresponding 4‐O‐mesylate 3 and the 4,7‐di‐O‐mesylate 4 as a by‐product. Compound 3 reacts with Nal giving the 4‐deoxy‐4‐iodo compound 5 with equatorial orientation of the I‐atom. As second product, the dihydrooxazole 6 is produced. Catalytic hydrogenation of 5 is followed by ester cleavage and removal of the isopropylidene group yielding the methyl α‐D‐ketoside 8 which affords the title compound, N‐acetyl‐4‐deoxyneuraminic acid (9), by reaction with fowl plague virus sialidase. Further biochemical activities of 8 and 9 are reported.
• Alkylation of N-acetylneuraminic acid at C-4
  作者：Avraham Liav

  DOI：10.1016/0008-6215(95)00069-6

  日期：1995.7