甲基4,7,8,9-四-O-乙酰基-2-硫代-N-乙酰基-alpha-D-神经氨酸甲酯 | 116450-06-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: 甲基4,7,8,9-四-O-乙酰基-2-硫代-N-乙酰基-alpha-D-神经氨酸甲酯
• 中文别名: 甲基-4,7,8,9-四-O-乙酰基-2-硫代-N-乙酰基-Α-D-神经氨酸甲酯；甲基- 4,7,8,9-四-O-乙酰基-2-硫代-N-乙酰基-Α-D-神经氨酸甲酯
• 英文名称: methyl (methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-glycero-α-D-galacto-2-nonulopyranosid)onate
• 英文别名: Methyl 4,7,8,9-tetra-O-acetyl-2-thio-N-acetyl-a-D-neuraminic acid methyl ester；methyl (2S,4S,5R,6R)-5-acetamido-4-acetyloxy-2-methylsulfanyl-6-[(1S,2R)-1,2,3-triacetyloxypropyl]oxane-2-carboxylate
• CAS: 116450-06-7
• 化学式: C₂₁H₃₁NO₁₂S
• 分子量: 521.543
• InChiKey: VUDPJAWMOISBAC-JSNLTNBWSA-N

物化性质

• 熔点：
  80-84 °C
• 沸点：
  609.9±55.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  35
• 可旋转键数：
  15
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  195
• 氢给体数：
  1
• 氢受体数：
  13

安全信息

• 危险品标志：
  T
• 安全说明：
  S23,S26,S36/37/39,S45,S53
• 危险类别码：
  R23/24/25,R45,R36/37/38,R46

反应信息

• 作为反应物：
  描述：

  甲基4,7,8,9-四-O-乙酰基-2-硫代-N-乙酰基-alpha-D-神经氨酸甲酯 在 sodium hydroxide 、 4 A molecular sieve 、 sodium methylate 、 DMTST 、 肼 作用下， 以 甲醇 、 乙腈 为溶剂， 生成 Neu(a2-6)Glc(b)-O-Bn
  参考文献：
  名称：

  Synthesis of ganglioside M5 from sea urchin egg

  摘要：

  A main component of ganglioside M5 from egg of the sea urchin, Anthocidaris crassispina, Neu5Gc alpha 2-->6Glc beta 1-->1Cer (1), which has N-glycolyl group in neuraminic acid part, as well as phytosphingosine and saturated nonhydroxy fatty acid in ceramide part was first synthesized starting from N-acetylneuraminic acid.

  DOI：

  10.1016/s0040-4039(00)77010-9
• 作为产物：
  描述：

  N-acetyl neuraminic acid 在 甲醇 、 Dowex 50W-X₈-200(H⁺) 、 sodium 作用下， 以 二氯甲烷 为溶剂， 反应 90.67h， 生成 甲基4,7,8,9-四-O-乙酰基-2-硫代-N-乙酰基-alpha-D-神经氨酸甲酯
  参考文献：
  名称：

  Hydrolase and sialyltransferase activities of Trypanosoma cruzi trans -sialidase towards NeuAc-α-2,3-Gal-β- O -PNP

  摘要：

  NeuAc-alpha -2,3-Gal-beta -O-PNP has been synthesised and its ability to act as a substrate for the hydrolase and transferase activities of Trypanosoma cruzi trans-sialidase have been investigated. The turn-over of this compound shows marked differences from the behaviour of NeuAc-MU. In addition, distinct differences in the action of T. cruzi trans-sialidase and Clostridium perfringens neuraminidase on NeuAc-alpha -2,3-Gal-beta -O-PNP were apparent. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00611-9

文献信息

• Benzeneselenenyl triflate as an activator of thioglycosides for glycosylation reactions
  作者：Yukishige Ito、Tomoya Ogawa、Masaaki Numata、Mamoru Sugimoto

  DOI：10.1016/0008-6215(90)84078-9

  日期：1990.7

  A new method for the activation of thioglycosides was developed by use of benzeneselenenyl triflate (PhSeOTf), which, upon reaction with either a primary or secondary sugar HO-group, afforded O-glycosides under extremely mild reaction conditions. The reaction was applicable to various l-thiohexosides 2-6 as well as to a 2-thioglycoside 20 derived from N-acetylneuraminic acid (NeuAc).

  通过使用苯硒烯基三氟甲磺酸酯（PhSeOTf），开发了一种活化硫代糖苷的新方法，该方法与伯或仲糖HO-基团反应后，在极其温和的反应条件下提供了O-糖苷。该反应适用于各种1-硫代己糖苷2-6以及衍生自N-乙酰神经氨酸（NeuAc）的2-硫代糖苷20。
• Synthesis, Enzymic, and NMR Studies of Novel Sialoside Probes: Unprecedented, Selective Neuraminidase Hydrolysis of and Inhibition by C-6-(methyl)-Gal Sialosides
  作者：Subramaniam Sabesan、Susana Neira、Fred Davidson、Jens O. Duus、Klaus Bock

  DOI：10.1021/ja00084a003

  日期：1994.3

  We report here the synthesis of sialoside analogs, namely, αDNeuAc(2-6)(6-Me,R)βGal-OR 1 (R isomer, tg rotamer analog) and αDNeuAc(2-6)(6-Me,S)βDGal-OR 1 (S isomer, gt rotamer analog, R 1 =CH 2 CH 2 SiMe 3 or H) and the corresponding sulfur links thiosialosides useful for the determination of carbohydrate structural requirements in neuraminidase hydrolysis and for the design of neuraminidase inhibiton

  我们在此报告唾液酸苷类似物的合成，即 αDNeuAc(2-6)(6-Me,R)βGal-OR 1（R 异构体，tg 旋转异构体类似物）和 αDNeuAc(2-6)(6-Me,S) βDGal-OR 1（S 异构体，gt 旋转异构体类似物，R 1 = CH 2 CH 2 SiMe 3 或 H）和相应的硫键硫代唾液酸，可用于确定神经氨酸酶水解中的碳水化合物结构要求和设计神经氨酸酶抑制剂
• Preparation of Sialyl Donors Carrying Functionalized Ester Substituents: Effects on the Selectivity of Glycosylation
  作者：Yukishige Ito、Akihiro Ishiwata

  DOI：10.1055/s-2003-40332

  日期：——

  various ester substituents were prepared systematically. Nucleophilic displacement of methyl ester with Ph 3 SiSH and CS 2 CO 3 followed by in situ alkylation with RX or esterification with R-OH/DCC afforded these compounds in good yields. Glycosylations promoted by NIS-TfOH were examined in order to examine the effect of substituent of the ester portion. When conducted in CH 3 CN, enhanced α-selectivities

  系统地制备了具有各种酯取代基的甲硫基唾液酸供体。用Ph 3 SiSH 和CS 2 CO 3 对甲酯进行亲核置换，然后用RX 原位烷基化或用R-OH/DCC 酯化，以良好的收率提供这些化合物。检查由 NIS-TfOH 促进的糖基化以检查酯部分取代基的影响。在 CH 3 CN 中进行时，观察到氰甲基、2-氰乙基、2-氰苄基和 2-硝基苄酯的 α 选择性增强，这意味着这些取代基可有效增强乙腈的溶剂效应，可能是通过稳定 β 取向腈离子。
• Study on systematizing the synthesis of the a-series ganglioside glycans GT1a, GD1a, and GM1 using the newly developed N-Troc-protected GM3 and GalN intermediates
  作者：Tatsuya Komori、Akihiro Imamura、Hiromune Ando、Hideharu Ishida、Makoto Kiso

  DOI：10.1016/j.carres.2009.06.009

  日期：2009.8

  A first systematic synthesis of the glycan parts of the a-series gangliosides (GT1a, GD1a, and GM1) utilizing the newly developed N-Troc-protected GM3 and galactosaminyl building blocks is described. The key processes, including the assembly of the GM2 sequence and its conversion into the 3-hydroxy acceptor, were facilitated mainly by the high degree of participation and chemoselective cleavability

  描述了利用新开发的N-Troc保护的GM3和半乳糖胺基结构单元对a系列神经节苷脂（GT1a，GD1a和GM1）的聚糖部分进行的首次系统合成。关键过程，包括GM2序列的组装及其向3-羟基受体的转化，主要是由于半乳糖胺基单元中Troc基团的高度参与性和化学选择性可切割性而促进的。此外，新型GM2受体在与半乳糖基，唾液酸半乳糖基和二唾液酸半乳糖基供体进行糖基化过程中，充当了良好的偶联伴侣，成功地生产了GM1，GD1a和GT1a聚糖。
• A facile, regio- and stereo-selective synthesis of ganglioside GM3
  作者：Takatoshi Murase、Hideharu Ishida、Makoto Kiso、Akira Hasegawa

  DOI：10.1016/0008-6215(89)84060-1

  日期：1989.6

  of 2-(trimethylsilyl)ethyl O-(6-O-benzoyl-beta-D-galactopyranosyl)-(1----4)- 2,6-di-O-benzoyl-beta-D-glucopyranoside (4), prepared from 2-(trimethylsilyl)ethyl beta-lactoside (1) by selective 3'-O-benzylation, O-benzoylation, and subsequent removal of the benzyl group, with methyl (methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-glycero-alpha-D- galacto - 2-nonulopyranosid)onate (5)

  已经合成了在神经酰胺部分包含三个不同脂肪酰基的神经节苷脂GM3。2-（三甲基甲硅烷基）乙基O-（6-O-苯甲酰基-β-D-吡喃半乳糖基）-（1 ---- 4）-2,6-二-O-苯甲酰基-β-D-吡喃葡萄糖苷（4由2-（三甲基甲硅烷基）乙基β-乳糖苷（1）通过选择性的3'-O-苄基化，O-苯甲酰化，然后除去苄基而制备，并用甲基（甲基5-乙酰氨基-4,7,8）制得使用三氟甲磺酸二甲基（甲硫基）s作为糖基助催化剂，得到9,9-四-O-乙酰基-3,5-二甲氧基-2-硫代-D-甘油-α-D-半乳糖基-2-壬基吡喃葡萄糖苷）（5） 2-（三甲基甲硅烷基）乙基O-（甲基5-乙酰氨基-4,7,8,9-四-O-乙酰基-3,5-二脱氧-D-甘油-α-D-半乳糖-2-壬基吡喃并磺酸+ +）- （2 ---- 3）-O-（6-O-苯甲酰基-β-D-吡喃半乳糖基）-（1 ---- 4）-2,6-二-O-苯甲酰基-β-D-吡喃葡萄糖苷（