Methyl 5-Acetamido-4,7,8,9-tetra-O-benzyl-3,5-dideoxy-D-glycero-D-galacto-non-2-enonate | 116096-63-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Methyl 5-Acetamido-4,7,8,9-tetra-O-benzyl-3,5-dideoxy-D-glycero-D-galacto-non-2-enonate
• 英文别名: methyl 5-acetamido-4,7,8,9-tetra-O-benzyl-2,3-dehydro-3,5-dideoxy-D-glycero-D-galacto-2-nonulopyranosonate；methyl (2R,3R,4S)-3-acetamido-4-phenylmethoxy-2-[(1S,2R)-1,2,3-tris(phenylmethoxy)propyl]-3,4-dihydro-2H-pyran-6-carboxylate
• CAS: 116096-63-0
• 化学式: C₄₀H₄₃NO₈
• 分子量: 665.783
• InChiKey: HKJHCUZMFCVFJX-MNNDNZQNSA-N

物化性质

• 沸点：
  798.0±60.0 °C(Predicted)
• 密度：
  1.22±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  49
• 可旋转键数：
  18
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  102
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  Methyl 5-Acetamido-4,7,8,9-tetra-O-benzyl-3,5-dideoxy-D-glycero-D-galacto-non-2-enonate 在 盐酸 、 Pd(OH)2/C 、 水 、 氢气 、 Selectfluor 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.5h， 生成 methyl 5-acetamido-5-deoxy-3-fluoro-D-erythro-L-manno-2-nonulopyranosonate
  参考文献：
  名称：

  Synthetic study of 3-fluorinated sialic acid derivatives

  摘要：

  Sialic acid derivatives, analogs, and their conjugates are expected to be pharmaceutical candidates such as anti-influenza drugs and also useful probes for investigating the biological role of glycoconjugates. Derivatives of 3-fluorinated sialic acid (3-F-Sia) have been found to be excellent probes in investigating functions and mechanisms of a series of proteins. Here, we describe the syntheses of 3-F-Sia derivatives, which are useful in making biologically important conjugate probes. A practical method for the construction of 3-fluorinated sialosides based on the stereoselective formation of the corresponding anomeric O-trimethylsilyl ether and their nucleophilic attack by an alkyl halide, an allyl halide in particular, was developed. In addition, details of the synthesis of cytidine monophosphate (CMP)-3-F-Sia bearing a fluorescent tag, which has been proven to show dual functions as a substrate of CMP-sialic acid transporter (CST) and an inhibitor of sialyltransferase (STase), are described. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2014.12.010
• 作为产物：
  描述：

  N-乙酰-2,3-二脱氢-2-脱氧神经氨酸 在 氢氧化钾 、 四丁基碘化铵 、 barium(II) oxide 作用下， 以 甲醇 、 乙醚 、 二甲基亚砜 为溶剂， 生成 Methyl 5-Acetamido-4,7,8,9-tetra-O-benzyl-3,5-dideoxy-D-glycero-D-galacto-non-2-enonate
  参考文献：
  名称：

  An efficient approach to streoselective glycosylation of N-acetylneuraminic acid: Used of phenylselenyl group as a stereocontrolling auxillary

  摘要：

  DOI：

  10.1016/s0040-4039(00)61852-x

文献信息

• Synthesis of Pyrrolidine Analogues ofN-Acetylneuraminic Acid as Potential Sialidase Inhibitors
  作者：L�szl� Czollner、J�nos Kuszmann、Andrea Vasella

  DOI：10.1002/hlca.19900730522

  日期：1990.8.8

  The pyrrolidine derivatives 3, 4, and 5 were prepared from the methyl ester 7 of Neu2en5Ac via lie pyrrolidine-borane adduct 33. They inhibit Vibrio cholerae sialidase competitively with Ki = 4. 4 10−3 M, 5. 3 10−3 M, and 4. 0 10−2 M, respectively. Benzylation of 7 gave the fully O-benzylated 8 besides 9, 10, and 11. Ozonolysis and reduction with NaBH4 of 8 and 9 gave the 1, 4-diols 12 and 15, the

  的吡咯烷衍生物3，4和5是从甲基酯制备7 Neu2en5Ac的经由谎言吡咯烷甲硼烷加成物33。它们分别以K i分别为4. 4 10 -3 M，5。3 10 -3 M和4. 0 10 -2 M抑制霍乱弧菌唾液酸酶。的苄基化7得到充分ø -benzylated 8除了9,10，和11臭氧分解和还原用NaBH 4的8和9分别得到1，4-二醇12和15，乙酸羟基酯13和16以及呋喃糖酶14和17（方案1）。二醇12被选择性保护（19 20 23），并通过Mitsunobu反应转化为叠氮化物27。容易的乙酰基迁移阻碍了由12获得的双乙酸酯22的选择性碱催化的脱保护。甲磺酸盐28被证明是不稳定的。叠氮化物27转化通过将29引入酮30中（方案2）。氢化30得到二氢吡咯31，因此得到吡咯32。加合物33通过施陶丁格反应（31）并用LiBH 4 / HBF 4还原而从30获得。它被转化为吡咯烷34。通过X射
• Halogen-directed chemical sialylation: pseudo-stereodivergent access to marine ganglioside epitopes
  作者：Taiki Hayashi、Alexander Axer、Gerald Kehr、Klaus Bergander、Ryan Gilmour

  DOI：10.1039/d0sc01219j

  日期：——

  components of the complex gangliosides that regulate cellular processes. Their importance in molecular recognition manifests itself in drug design (e.g. Tamiflu®) and continues to stimulate the development of effective chemical sialylation strategies to complement chemoenzymatic technologies. Stereodivergent approaches that enable the α- or β-anomer to be generated at will are particularly powerful to attenuate

  唾液酸是调节细胞过程的复杂神经节苷脂的显着结构成分。它们在分子识别中的重要性体现在药物设计中（例如Tamiflu®），并继续刺激有效化学唾液酸化策略的发展，以补充化学酶技术。能够随意产生α-或β-异头物的立体发散方法特别有效地减弱了氢键网络和询问功能。在本文中，我们证明了N的C3处的位点选择性卤化（F和Br）海洋Neu2,6Glu表位共有的β-甘氨酰单元可实现假立体发散的唾液酸化。氟化可产生α-选择性唾液酸化作用，而无痕溴引导的唾液酸化作用则可产生β加合物。该概念在HLG-1和Hp-s1类似物的合成中得到验证。
• Synthesis of a Phosphonic Acid Analogue ofN-Acetyl-2,3-didehydro-2-deoxyneuraminic Acid, an Inhibitor ofVibrio cholerae Sialidase
  作者：Andrea Vasella、Ren� Wyler

  DOI：10.1002/hlca.19910740223

  日期：1991.3.13

  The synthesis of the phospha analogue 10 of DANA (2) is described. Bromo-hydroxylation of the known 11 ( 12 and 13) followed by treatment of the major bromohydrin 13 with 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) gave the oxirane 14 (Scheme 1). Depending on the solvent, TiBr4 transformed 14 into 16 or into a 15/16 mixture. Reductive debromination of 16 ( 17), followed by benzylation provided 18. Oxidattve

  描述了DANA（2）的磷酸酯类似物10的合成。已知11（12和13）的溴羟基化，然后用1，8-二氮杂双环[5.4.0]十一碳-7-烯（DBU）处理主要的溴代醇13，得到环氧乙烷14（方案1）。取决于溶剂，TiBr 4转化14至16或进入15 / 16混合物。还原脱溴化16（17），然后进行苄基化，得到18。通过18的皂化获得的酸的氧化脱羧（Pb（OAc）4）产生异头乙酸酯19和20。而19是惰性phosphonoylation的条件下，更具反应性的亚氨酸酯22，以一起获得23从19 / 20经由21（方案2），得到膦酸酯的混合物，24 / 25和双环缩醛26。去苄基化24 / 25和乙酰化导致acetoxyphosphonates 27/ 28。由于从AcOH中的β消去27 / 28被证明是困难，溴化物34制备自27 / 28通过photobromination并进行还原消除用Zn / Cu的（35
• Highly stereoselective glycosylation of sialic acid aided by stereocontrolling auxiliaries
  作者：Yukishige Ito、Tomoya Ogawa

  DOI：10.1016/s0040-4020(01)97586-6

  日期：1990.1

  .alpha.-Selective glycosylation of sialic acid was achieved by using a sialic acid donor which carries a stereocontrolling auxiliary such as selenide or sulfide group at C-3 position.
• Highly stereoselective glycosylation of N-acetylneuraminic acid aided by a phenylthio substituent as a stereocontrolling auxilliary
  作者：Yukishige Ito、Tomoya Ogawa

  DOI：10.1016/s0040-4039(00)80400-1

  日期：1988.1