2-(trimethylsilyl)ethyl 2,3-di-O-benzoyl-6-O-benzyl-β-D-galactopyranoside | 117252-98-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(trimethylsilyl)ethyl 2,3-di-O-benzoyl-6-O-benzyl-β-D-galactopyranoside
• 英文别名: [(2R,3S,4S,5R,6R)-5-benzoyloxy-3-hydroxy-2-(phenylmethoxymethyl)-6-(2-trimethylsilylethoxy)oxan-4-yl] benzoate
• CAS: 117252-98-9
• 化学式: C₃₂H₃₈O₈Si
• 分子量: 578.734
• InChiKey: BYQLKIXRFUDWLS-XSCYCRSJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  41.0
• 可旋转键数：
  12.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  100.52
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  2-(trimethylsilyl)ethyl 2,3-di-O-benzoyl-6-O-benzyl-β-D-galactopyranoside 在 2,4,6-三甲基吡啶 、 4 A molecular sieve 、 sodium methylate 、 silver trifluoromethanesulfonate 作用下， 以 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 12.0h， 生成 2-(trimethylsilyl)ethyl 6-O-benzyl-4-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-β-D-galactopyranoside
  参考文献：
  名称：

  2-(Trimethylsilyl)ethyl glycosides. 3. Synthesis, anomeric deblocking, and transformation into 1,2-trans 1-O-acyl sugars

  摘要：

  DOI：

  10.1021/jo00259a006
• 作为产物：
  描述：

  2-(trimethylsilyl)ethyl 4,6-O-benzylidene-β-D-galactopyranoside 在 吡啶 、 盐酸 、 4 A molecular sieve 、 sodium cyanoborohydride 作用下， 以 四氢呋喃 为溶剂， 反应 15.0h， 生成 2-(trimethylsilyl)ethyl 2,3-di-O-benzoyl-6-O-benzyl-β-D-galactopyranoside
  参考文献：
  名称：

  2-(Trimethylsilyl)ethyl glycosides. 3. Synthesis, anomeric deblocking, and transformation into 1,2-trans 1-O-acyl sugars

  摘要：

  DOI：

  10.1021/jo00259a006

文献信息

• Efficient O-Functionalization of Carbohydrates with Electrophilic Reagents
  作者：Gergely L. Tolnai、Ulf J. Nilsson、Berit Olofsson

  DOI：10.1002/anie.201605999

  日期：2016.9.5

  iodonium(III) reagents. Both electron‐withdrawing and electron‐donating aryl groups were introduced under ambient conditions and without precautions to exclude air or moisture. Furthermore, the approach was extended both to full arylation of cyclodextrin, and to trifluoroethylation of carbohydrate derivatives. This is the first general approach to introduce traditionally non‐electrophilic groups into

  使用稳定且易于制备的碘(III)试剂建立了碳水化合物衍生物O-功能化的新方法。吸电子芳基和供电子芳基都是在环境条件下引入的，并且没有采取措施排除空气或湿气。此外，该方法还扩展到环糊精的完全芳基化和碳水化合物衍生物的三氟乙基化。这是将传统非亲电基团引入糖主链周围的任何 OH 基团的第一个通用方法。该方法将适用于合成有机化学和生物化学，因为重要的官能团可以在简单而稳健的反应条件下以快速有效的方式掺入。
• Influence of saccharide size on the cellular immune response to glycopeptides
  作者：Mickael Mogemark、Thomas P. Cirrito、Petter Sjölin、Emil R. Unanue、Jan Kihlberg

  DOI：10.1039/b301747h

  日期：——

  trigalactosylated derivative of an immunogenic peptide from hen egg-white lysozyme (HEL52-61) was prepared. Synthesis was accomplished by assembly of an alpha-1,4-linked trigalactose peracetate which was coupled to Fmoc serine. After activation as a pentafluorophenyl ester the resulting building block was used in solid-phase synthesis In contrast to the corresponding mono- and digalactosylated derivatives of HEL52-61

  与抗原呈递细胞上的MHC分子结合的糖肽可能会诱发碳水化合物选择性T细胞。为了研究细胞免疫应答如何取决于碳水化合物部分的大小，制备了一种来自鸡蛋清溶菌酶（HEL52-61）的免疫原性肽的三半乳糖基化衍生物。通过组装与Fmoc丝氨酸偶联的α-1，4-连接的三半乳糖过乙酸酯来完成合成。活化为五氟苯基酯后，将所得结构单元用于固相合成。与HEL52-61的相应单-和半乳糖基化衍生物相反，三乳糖基化的HEL52-61没有免疫原性。有点令人惊讶 发现这是因为三半乳糖基衍生物与I-Ak MHC分子的结合比单半乳糖基和二半乳糖基肽弱约两个数量级。我们的观察结果为以前的发现提供了解释，这些发现表明从自然界中的MHC分子中分离出的糖肽通常携带小糖。
• Synthesis of a Single Repeat Unit of Type VIII Group B<i>Streptococcus</i>Capsular Polysaccharide¹
  作者：Eva Eichler、Harold J. Jennings、Dennis M. Whitfield

  DOI：10.1080/07328309708007324

  日期：1997.5

  We have synthesized a single repeat unit of type VIII Group B Streptococcus capsular polysaccharide, the structure of which is L-Rhap(beta 1-->4)-D-Glcp(beta 1-->4) [Neu5Ac(alpha 2-->3)]-D-Galp(beta 1-->4}(n). The synthesis presented three significant synthetic challenges namely: the L-Rhap(beta 1-->4)-D-Glcp bond, the Neu5Ac(alpha 2-->3)-D-Galp bond and 3,4-D-Galp branching. The L-Rhap bond was constructed in 60% yield (alpha:beta l:1.2) using 4-O-acetyl-2, 3-di-O-benzoyl-alpha-L-rhamnopyranosyl bromide 6 as donor, silver silicate as promotor and 6-O-benzyl-2,3-di-O-benzoyl-1-thio-beta-D-glucopyranoside as acceptor to yield disaccharide 18. The Neu5Ac(alpha 2-->3) linkage was synthesized in 66% yield using methyl [phenyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-glycero-D-galacto-nonulopyranosid]onate as donor and triol 2-(trimethylsilyl) ethyl 6-O-benzyl-beta-D-galactopyranoside as acceptor to give disaccharide 21. The 3,4-D-Galp branching was achieved by regioselective glycosylation of disaccharide diol 21 by disaccharide 18 in 28% yield to give protected tetrasaccharide 22. Tetrasaccharide 22 was deprotected to give as its 2-(trimethylsilyl)ethyl glycoside the title compound 1a. In addition the 2-(trimethylsilyl)ethyl group was cleaved and the tetrasaccharide coupled by glycosylation (via tetrasaccharide trichloroacetimidate) to a linker suitable for conjugation.
• Sjoelin, Petter; George, Shaji K.; Bergquist, Karl-Erik, Journal of the Chemical Society. Perkin transactions I, 1999, # 12, p. 1731 - 1742
  作者：Sjoelin, Petter、George, Shaji K.、Bergquist, Karl-Erik、Roy, Sarbari、Svensson, Anette、Kihlberg, Jan

  DOI：——

  日期：——
• JANSSON, KARL;AHLFORS, STEFAN;FREJD, TORBJORN;KIHLBERG, JAN;MAGNUSSON, GO+, J. ORG. CHEM., 53,(1988) N 24, C. 5629-5647
  作者：JANSSON, KARL、AHLFORS, STEFAN、FREJD, TORBJORN、KIHLBERG, JAN、MAGNUSSON, GO+

  DOI：——

  日期：——