2-(trimethylsilyl)ethyl 6-O-benzyl-β-D-galactopyranoside | 192706-11-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(trimethylsilyl)ethyl 6-O-benzyl-β-D-galactopyranoside
• 英文别名: (2R,3R,4S,5R,6R)-2-(phenylmethoxymethyl)-6-(2-trimethylsilylethoxy)oxane-3,4,5-triol
• CAS: 192706-11-9
• 化学式: C₁₈H₃₀O₆Si
• 分子量: 370.518
• InChiKey: IJBPENMJKZEJAX-DISONHOPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.37
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  88.4
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-(trimethylsilyl)ethyl 6-O-benzyl-β-D-galactopyranoside 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三氟乙酸 作用下， 以 吡啶 、 二氯甲烷 为溶剂， 反应 9.0h， 生成 O-(2,3,4-tri-O-acetyl-6-O-benzyl-α-D-galactopyranosyl) trichloroacetimidate
  参考文献：
  名称：

  VIII型B组链球菌荚膜多糖的二烯丙基化六糖的合成。

  摘要：

  作为设计，开发和制备针对细菌病原体B组链球菌的保护性疫苗的计划的一部分，我们报告了二唾液酸化六糖的合成。此六糖代表VIII型血清型特异性荚膜多糖的一部分，该多糖具有四糖重复单元[β-L-Rhap-（1-> 4）-β-D-Glcp-（1-> 4）- [α-Neu5Ac-（2-→3）]-β-D-Galp-（1→4）] n。我们已经合成了与该重复单元相对应的四糖。Eichler，HJ Jennings，DM Whitfield，J.Carbohydr。Chem。，16（1997）385-411]。由于认为保护性表位涉及几个重复单元，因此研究了扩展该四糖的方法。这个目标要求将β-L-Rhap的非反应性OH-4进行糖基化，这是通过将D-Galp糖基三氯乙酰亚氨酸酯供体与β-L-Rhap-（1→4）-D-Glcp受体偶联来实现的。随后将该三糖作为供体偶联至α-Neu5Ac-（2-→3）-D-Galp二

  DOI：

  10.1016/s0008-6215(99)00103-2
• 作为产物：
  描述：

  2-(trimethylsilyl)ethyl 2,3-di-O-benzoyl-6-O-benzyl-β-D-galactopyranoside 在 sodium methylate 作用下， 以 甲醇 为溶剂， 以66%的产率得到2-(trimethylsilyl)ethyl 6-O-benzyl-β-D-galactopyranoside
  参考文献：
  名称：

  Synthesis of a Single Repeat Unit of Type VIII Group BStreptococcusCapsular Polysaccharide¹

  摘要：

  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.

  DOI：

  10.1080/07328309708007324

文献信息

• Efficient Synthesis of a Sialic Acid α(2→3)Galactose Building Block and Its Application to the Synthesis of Ganglioside GM3
  作者：Yunpeng Liu、Xiaohong Ruan、Xiangpeng Li、Yingxia Li

  DOI：10.1021/jo800138p

  日期：2008.6.1

  with up to 73% yield and 8.4:1 stereoselectivity, was realized when 2,3,4-unprotected galactose derivatives and TBSOTf were used as acceptors and promoter, respectively. Sialylation of 2-(trimethylsilyl)ethyl 6-O-tert-butyldiphenylsilyl-β-d-galactopyranoside (3f) gave the best result, and the resultant Neu5Ac α(2→3)Gal disaccharide was successfully used in the synthesis of ganglioside GM3.

  研究了以O-乙酰化唾液酸N-苯基三氟乙酰亚氨酸酯为供体的各种半乳糖衍生物的糖基化。当分别将2,3,4-未保护的半乳糖衍生物和TBSOTf用作受体和启动子时，实现了半乳糖的高效α（2,3）唾液酸化，产率高达73％，立体选择性高达8.4：1。的2-唾液酸化（三甲基硅烷基）乙基-6- ø -叔-butyldiphenylsilyl-β-d吡喃半乳糖苷（3F），得到最好的结果，并且将所得的Neu5Acα（2→3）半乳糖二糖在神经节苷脂GM3的合成成功地用于。
• 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.
• Synthesis of a disialylated hexasaccharide of Type VIII Group B Streptococcus capsular polysaccharide
  作者：Eva Eichler、Harold J. Jennings、Michel Gilbert、Dennis M. Whitfield

  DOI：10.1016/s0008-6215(99)00103-2

  日期：1999.6

  bacterial pathogens Group B Streptococcus, we report the synthesis of a disialylated hexasaccharide. This hexasaccharide represents a portion of the serotype-specific capsular polysaccharide of Type VIII that has the tetrasaccharide repeat unit [beta-L-Rhap-(1-->4)-beta-D-Glcp-(1-->4)-[alpha-Neu5Ac-(2--> 3)]-beta-D- Galp-(1-->4)]n. A tetrasaccharide corresponding to this repeat unit has been synthesized

  作为设计，开发和制备针对细菌病原体B组链球菌的保护性疫苗的计划的一部分，我们报告了二唾液酸化六糖的合成。此六糖代表VIII型血清型特异性荚膜多糖的一部分，该多糖具有四糖重复单元[β-L-Rhap-（1-> 4）-β-D-Glcp-（1-> 4）- [α-Neu5Ac-（2-→3）]-β-D-Galp-（1→4）] n。我们已经合成了与该重复单元相对应的四糖。Eichler，HJ Jennings，DM Whitfield，J.Carbohydr。Chem。，16（1997）385-411]。由于认为保护性表位涉及几个重复单元，因此研究了扩展该四糖的方法。这个目标要求将β-L-Rhap的非反应性OH-4进行糖基化，这是通过将D-Galp糖基三氯乙酰亚氨酸酯供体与β-L-Rhap-（1→4）-D-Glcp受体偶联来实现的。随后将该三糖作为供体偶联至α-Neu5Ac-（2-→3）-D-Galp二