Neu5Ac(2-6)Gal | 875136-19-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Neu5Ac(2-6)Gal
• 英文别名: 1,2:3,4-di-O-isopropylidene-6-O[methyl (5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-D-galacto-nonulopyranosyl)onate]-α-D-galactopyranoside；methyl (4S,5R,6R)-5-acetamido-4-acetyloxy-2-[[(1S,2R,6R,8R,9S)-4,4,11,11-tetramethyl-3,5,7,10,12-pentaoxatricyclo[7.3.0.02,6]dodecan-8-yl]methoxy]-6-[(1S,2R)-1,2,3-triacetyloxypropyl]oxane-2-carboxylate
• CAS: 875136-19-9
• 化学式: C₃₂H₄₇NO₁₈
• 分子量: 733.721
• InChiKey: MRBFIFCARWEKFL-YSPPFVHXSA-N

物化性质

• 沸点：
  748.2±60.0 °C(Predicted)
• 密度：
  1.35±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  51
• 可旋转键数：
  17
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  225
• 氢给体数：
  1
• 氢受体数：
  18

反应信息

• 作为产物：
  描述：

  N-acetyl-4,7,8,9-tetra-O-acetyl-2-chloro-2-deoxyneuraminic acid methyl ester 在 15-冠醚-5 、 silver trifluoromethanesulfonate 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 1.5h， 生成 Neu5Ac(2-6)Gal
  参考文献：
  名称：

  Thiomidoyl approach to the synthesis of α-sialosides

  摘要：

  Novel sialosyl donors, S-benzoxazolyl (SBox) and S-thiazolyl (STaz) sialosides, have been synthesized and applied to the stereoselective synthesis of alpha-sialosides. It was also demonstrated that it is possible to selectively activate SBox sialyl donor over ethyl thioglycoside, allowing the direct synthesis of disaccharide donors that could be used in subsequent glycosylations without further manipulations. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.11.043

文献信息

• Thioester-assisted α-sialylation reaction
  作者：Shinya Hanashima、Shoji Akai、Ken-ichi Sato

  DOI：10.1016/j.tetlet.2008.05.154

  日期：2008.8

  α-Selective sialylation reactions were carried out using novel sialic acid building blocks that possess a thioester auxiliary. In contrast to other arylthio- and benzylthioester derivatives, sialyl phosphite 1a (with the phenylthioester moiety) was employed as the α-selective building block, and was reacted with various primary alcohols, including the C6–OH group of galactose and glucose, with moderate

  使用具有硫酯助剂的新型唾液酸结构单元进行α-选择性唾液酸化反应。与其他芳基硫代和苄基硫代酯衍生物相比，亚磷酸唾液酸基酯1a（具有苯基硫代酯部分）被用作α-选择性结构单元，并与各种伯醇（包括半乳糖和葡萄糖的C6-OH基团）反应，具有出色的α选择性。对于半乳糖的C3-OH，4，6-二-O-苄基半乳糖具有所需的α-键，且选择性极好。
• Novel glycosylation reactions using glycosyl thioimidates of N-acetylneuraminic acid as sialyl donors
  作者：Kiyoshi Ikeda、Misato Aizawa、Kazuki Sato、Masayuki Sato

  DOI：10.1016/j.bmcl.2006.02.037

  日期：2006.5

  Novel sialyl donors 4 bearing a thioimidolyl moiety as the leaving group were successfully prepared from the corresponding arylthio derivatives 3 and a peracetylated chloro derivative of Neu5Ac 2 in the presence of N,N-di-isopropylethylamine with moderate yields. The reaction of 4 with various alcohols 5 was effectively activated by AgOTf as the promoter to give the corresponding O-sialosides 6 with

  在N，N-二异丙基乙胺存在下，由Neu5Ac 2的相应的芳基硫代衍生物3和过乙酰化的氯代衍生物成功地制备了带有硫代亚氨基基部分作为离去基团的新的唾液酸给体4，产率适中。AgOTf作为促进剂有效地活化了4与各种醇5的反应，从而以高收率得到了相应的O-唾液酸苷6。还用AgOTf实现了Neu5Ac 7的4-戊烯基2-糖苷上的4a的选择性活化。
• Concentration Dependence of Glycosylation Outcome: A Clue to Reproducibility and Understanding the Reasons Behind
  作者：Leonid O. Kononov、Nelly N. Malysheva、Anna V. Orlova、Alexander I. Zinin、Tatiana V. Laptinskaya、Elena G. Kononova、Natalya G. Kolotyrkina

  DOI：10.1002/ejoc.201101613

  日期：2012.4

  Changes in the concentration of reagents (0.009–0.2 M) have been shown to dramatically effect the yield and stereoselectivity of glycosylation with a sialic acid based glycosyl donor in a complex nonlinear manner that correlates with changes in the structures of the supramers of the reagents. The yield of disaccharide gradually increases with concentration and levels off at concentrations of glycosyl

  已显示试剂浓度的变化 (0.009–0.2 M) 以复杂的非线性方式显着影响基于唾液酸的糖基供体的糖基化的产率和立体选择性，这与试剂超聚体结构的变化相关。二糖的产量随着浓度的增加而逐渐增加，并在糖基供体浓度高于 69 mM 时趋于平稳。异头物的比例在某些浓度下非常高 (α/β ≈ 20:1)，在其他浓度下为中等 (α/β ≈ 8:1) 或非常低 (α/β ≈ 4:1)。通过旋光法和激光散射检测到浓度超过 69 mM 的糖基供体和糖基受体的混合超聚体的形成。
• Preparation of 4-Pentenoic Acid Ester of Neu5Ac and 4-Pentenyl Glycoside of Neu5Ac and Their Application to Glycosylation
  作者：Kiyoshi Ikeda、Jun Fukuyo、Kazuki Sato、Masayuki Sato

  DOI：10.1248/cpb.53.1490

  日期：——

  Novel sialosyl donors, 4-pentenoic acid ester of N-acetylneuraminic acids (Neu5Ac) (1a) and 4-pentenyl glycoside of Neu5Ac (1b) were successfully prepared from the corresponding per-O-acetylated 2-hydroxy and 2-chloro derivatives of Neu5Ac, respectively and applied to the synthesis of O-sialosides.

  分别从相应的全-O-乙酰化的2-羟基和2-氯衍生物中成功制备了新型唾液酸供体——N-乙酰神经氨酸（Neu5Ac）的4-戊烯酸酯（1a）和Neu5Ac的4-戊烯基糖苷（1b），并将其应用于O-唾液酸苷的合成。
• “Active” and “latent” thioglycosyl donors in oligosaccharide synthesis. Application to the synthesis of α-sialosides
  作者：René Roy、Fredrik O. Andersson、Marie Letellier

  DOI：10.1016/s0040-4039(00)60004-7

  日期：1992.10

  The use of a new "active" and "latent" thioglycosyl donor strategy in glycoside synthesis is described using arylthio alpha-sialosides of different reactivities.