trimethylsilyl 2,3,4,6-tetra-O-acetyl-α-D-galactopyranoside | 123163-89-3

• 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
• 英文名称: trimethylsilyl 2,3,4,6-tetra-O-acetyl-α-D-galactopyranoside
• 英文别名: [(2R,3S,4S,5R,6R)-3,4,5-triacetyloxy-6-trimethylsilyloxyoxan-2-yl]methyl acetate
• CAS: 123163-89-3
• 化学式: C₁₇H₂₈O₁₀Si
• 分子量: 420.489
• InChiKey: NRJIIUKUAQBWBU-DRRXZNNHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.92
• 重原子数：
  28.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  123.66
• 氢给体数：
  0.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  methyl 2,3,4-tri-O-benzoyl-6-O-(tert-butyldiphenylsilyl)-β-D-galactopyranoside 、 trimethylsilyl 2,3,4,6-tetra-O-acetyl-α-D-galactopyranoside 在 三氟甲磺酸三甲基硅酯 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 48.0h， 以47%的产率得到methyl O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1<*>6)-2,3,4-tri-O-benzoyl-β-D-galactopyranoside
  参考文献：
  名称：

  Coupling reactions of O-(trimethylsilyl) glycosides and 6-O-(tert-butyldiphenylsilyl)-protected galactosides in the presence of trimethylsilyl triflate. A new method of forming .beta.-(1 .fwdarw. 6)-oligosaccharidic linkages

  摘要：

  DOI：

  10.1021/jo00287a026
• 作为产物：
  描述：

  trimethylsilyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside 生成 trimethylsilyl 2,3,4,6-tetra-O-acetyl-α-D-galactopyranoside
  参考文献：
  名称：

  JUNG, GRACE L.;HOLME, KEVIN R.;GLAUDEMANS, CORNELIS P. J.;LEHMANN, JOCHEN+, CARBOHYDR. RES., 174,(1988) 87-98

  摘要：

  DOI：

文献信息

• Selective Acetylation of Non-anomeric Groups of per-<i>O</i>-Trimethylsilylated Sugars
  作者：Welday Desta Weldu、Cheng-Chung Wang

  DOI：10.1021/acs.joc.0c02813

  日期：2021.4.2

  Selective modification of the hydroxyl groups of sugars has been a long-standing challenge due to their proximate relative reactivity. Herein, we report a TMSOTf-catalyzed selective acetylation of the non-anomeric hydroxyl groups of several per-O-TMS-protected sugar substrates while leaving their anomeric group unaffected. In addition to standing versatile by itself, the anomeric O-TMS group left intact

  糖的羟基的选择性修饰由于其近乎相对的反应性而一直是一个长期的挑战。本文中，我们报道了TMSOTf催化的几种过O -TMS保护的糖底物的非异头羟基的选择性乙酰化，同时不影响其异头基团。除了本身具有通用性之外，可以将完整的异头O -TMS基团官能化，以提供关键的糖前体，如亚氨酸酯供体，否则可以通过逐步的异头脱保护-官能化程序进行合成。
• Iodine-hexamethyldisilane (HMDS)-mediated anomerization of peracetylated 1,2-trans-linked alkyl and aryl glycosides
  作者：Satish Malik、Krupesh J. Shah、K.P. Ravindranathan Kartha

  DOI：10.1016/j.carres.2010.02.012

  日期：2010.5

  peracetylated alkyl and aryl 1,2-trans-glycosides with iodine in the presence of HMDS has been found to result in the anomerization leading to the formation of the respective 1,2-cis-glycosides. In the case of alkyl glycosides with aglycons of short alkyl chain length complete anomerization to the alpha-glycosides was observed while with those of longer chain length the process was found to be incomplete

  已经发现在HMDS存在下用碘处理过乙酰化的烷基和芳基1，2-反式-糖苷会导致异构化，从而导致形成相应的1，2-顺式-糖苷。在具有短烷基链长的糖苷配基的烷基糖苷的情况下，观察到完全糖化为α-糖苷，而对于那些具有较长链长的糖苷，发现该过程是不完全的。这些观察已被机械地解释了。
• 3-Azi-1-methoxybutyl β-d-galactopyranoside, a photoaffinity label for monoclonal antigalactan antibodies of the VH gal 39.1/55.1 gene-family
  作者：Grace L. Jung、Kevin R. Holme、Cornelis P.J. Glaudemans、Jochen Lehmann、Helga Lay

  DOI：10.1016/0008-6215(88)85083-3

  日期：1988.3

  3-Azi-1-methoxybutyl beta-D-galactopyranoside, prepared from 2,3,4,6-tetra-O-acetyl-alpha-D-galactopyranosyl bromide in four steps, had an affinity constant for antigalactans IgA (Fab') J539 and X24 of 1550 and 1730 M-1, respectively. 3-Azi-1-methoxybutyl beta-D-(4-3H)galactopyranoside, when photolysed in the presence of IgA X24, specifically labelled the galactan-binding area of the immunoglobulin

  由2,3,4,6-四-O-乙酰基-α-D-吡喃半乳糖基溴化物分四个步骤制得的3-Azi-1-甲氧基丁基β-D-吡喃半乳糖苷具有对半乳聚糖IgA（Fab'）的亲和常数。 J539和X24分别为1550和1730 M-1。当在IgA X24存在下光解时，3-Azi-1-甲氧基丁基β-D-（4-3H）吡喃半乳糖苷特别标记了免疫球蛋白的半乳聚糖结合区。
• Stereoselective trimethylsilylation of α- and β-galactopyranoses
  作者：Yuri Asami、Yuka Kawaguchi、Yoshimi Kanie、Hajjaj Abdu-Allah、Katsuhiko Suzuki、Osamu Kanie

  DOI：10.1016/j.carres.2019.01.013

  日期：2019.2

  Trimethylsilylation of the anomeric hydroxyl groups of tetra-O-benzyl and tetra-O-acetyl galactopyranoses was investigated. Stereoselective formation of β-trimethylsilyl glycoside (β-TMS glycoside) of benzyl protected compound was achieved using N-trimethylsilyl diethylamine. In the course of the investigation of the selective synthesis of TMS galactosides using TMS-imidazole, we observed the formation

  研究了四-O-苄基和四-O-乙酰基吡喃半乳糖的异头羟基的三甲基甲硅烷基化。使用N-三甲基甲硅烷基二乙胺可实现立体选择性地形成苄基保护化合物的β-三甲基甲硅烷基糖苷（β-TMS糖苷）。在研究使用TMS-咪唑选择性合成TMS半乳糖苷的过程中，我们观察到了中间体的形成，该中间体在硅胶柱色谱分离后主要转化为α-TMS糖苷。使用TMS-三氟甲磺酸-2,6-lutindine进行的乙酰化化合物反应选择性地产生α-TMS糖苷。
• Rational Design and Synthesis of a 1,1-Linked Disaccharide That Is 5 Times as Active as Sialyl Lewis X in Binding to E-Selectin
  作者：Kazumi Hiruma、Tetsuya Kajimoto、Gabriel Weitz-Schmidt、Ian Ollmann、Chi-Huey Wong

  DOI：10.1021/ja9611093

  日期：1996.1.1

  We describe here a rational design and synthesis of (3-O-carboxymethyl)-beta-D-galactopyranosyl alpha-D-mannopyranoside which is 5 times as active as sialyl Lewis X in binding to E-selectin and also effective against P- and L-selectin. A new method for the 1,1-glycosidic bond formation via coupling of protected trimethylsilyl beta-D-galactoside and alpha-mannosyl fluoride in the presence of BF3 . Et(2)O is described.