2-(trimethylsilyl)ethyl 2,3-di-O-benzyl-β-D-glucopyranoside | 152771-01-2

• 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-benzyl-β-D-glucopyranoside
• 英文别名: (2R,3R,4S,5R,6R)-2-(hydroxymethyl)-4,5-bis(phenylmethoxy)-6-(2-trimethylsilylethoxy)oxan-3-ol
• CAS: 152771-01-2
• 化学式: C₂₅H₃₆O₆Si
• 分子量: 460.643
• InChiKey: BUXNTEWTBVXRIB-NHTNDUFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.59
• 重原子数：
  32
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  77.4
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-(trimethylsilyl)ethyl 2,3-di-O-benzyl-β-D-glucopyranoside 在 吡啶 、 盐酸 、 potassium dichromate 、 硫酸 、 sodium hydride 、 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 29.0h， 生成 methyl [2-(trimethylsilyl)ethyl 2,3-di-O-benzyl-4-O-methyl-β-D-glucopyranosid]uronate
  参考文献：
  名称：

  Syntheses of model compounds related to an antigenic epitope in pectic polysaccharides from Bupleurum falcatum L.

  摘要：

  Stereocontrolled syntheses of model compounds related to a category of the major antigenic epitope against anti-bupleurum 2IIc/PG-1-IgG from an anti-ulcer pectic polysaccharide are described. Glycosylation of the glucuronic acid donors methyl(2,3-di-O-benzoyl-4-O-methyl-alpha -D-glucopyranosyl trichloroacetimidate)uronate and methyl (2,3-di-O-benzoyl-4-O-methyl-beta -D-glucopyranosyl)uronate-(1 -->6)-2,3,4-tri-O-benzoyl-alpha -D-galactopyranosyl trichloroacetimidate with the common acceptor 2-(trimethylsilyl)ethyl 2,3,4-tri-O-benzyl-beta -D-galactopyranoside in the presence of trimethylsilyl triflate (TMSOTf) gave the desired di- and trisaccharide derivatives. Furthermore the products were transformed into the oligo-valent clustering saccharides, N,N',N"-tri-{5-[4-O-methyl-beta -D-glucopyranosyluronic acid-(1 --> 6)-beta -D-galactopyranosyloxy]pentylcarbonylaminoethyl}-1,3,5-benzenetriamide and N,N',N"-tri-{5-[4-O-methyl-beta -D-glucopyranosyluronic acid (1 --> 6)-beta -D-galactopyranosyl-(1 --> 6)-beta -D-galactopyranosyloxy]pentylcarbonylaminoethyl}-1,3,5-benzenetriamide. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(01)00148-3
• 作为产物：
  描述：

  2-(trimethylsilyl)ethyl β-D-glucopyranoside 在 盐酸 、 sodium hydride 、 对甲苯磺酸 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 10.0h， 生成 2-(trimethylsilyl)ethyl 2,3-di-O-benzyl-β-D-glucopyranoside
  参考文献：
  名称：

  具有固定羧酸基团的Sialyl Lewis x模拟物的合成：阐明Sialyl Lewis x生物活性构象的化学方法。

  摘要：

  溶液和唾液酸化的路易斯x（sLe（x））的生物活性构象之间的关系已通过化学方法解决。为了模拟sLe（x）1的最佳溶液构象，设计并合成了更刚性的类似物2。1的唾液酸残基被固定在与半乳糖融合的六元环缩醛的赤道位置的羧酸官能团取代。由于熵的考虑，如果优选的溶液构象和sLe（x）的结合形式相似，则有望提高生物活性。由于在E-选择素结合测定中发现模拟物2是无活性的，因此sLe（x）的结合形式很可能与当时的溶液构象不同。

  DOI：

  10.1021/jo951067l

文献信息

• Synthesis of the monodeoxy derivatives of 2-(trimethylsilyl)ethyl β-lactoside
  作者：Tomas Ekberg、Göran Magnusson

  DOI：10.1016/0008-6215(93)84028-5

  日期：1993.8

  Monodeoxy derivatives of 2-(trimethylsilyl)ethyl (Me3SiEt) beta-lactoside were synthesized, by deoxygenation at the disaccharide level, for the 2'-, 3'-, 4'-, and 6'-monodeoxylactosides. The 2-, 3-, and 6-deoxy derivatives were synthesized by beta-D-galactosylation of suitably protected monodeoxygenated Me3SiEt glucosides. Silver silicate was shown to be an efficient glycosylation promoter in the preparation

  通过在二糖水平上脱氧，合成2-（三甲基甲硅烷基）乙基（Me 3 SiEt）β-乳糖苷的单脱氧衍生物，用于2'-，3'-，4'-和6'-单脱氧乳糖苷。通过适当保护的单脱氧Me3SiEt葡糖苷的β-D-半乳糖基化合成2-，3-和6-脱氧衍生物。在制备2-和3-脱氧乳糖苷中，硅酸银被证明是有效的糖基化促进剂。
• A Chemical Synthesis of GlcNAcβ(1→4)GlcUA-UDP to Elucidate the Catalytic Mechanism of Hyaluronic Acid Synthases (HAS)
  作者：Hironao Takaku、Makoto Kiso、Hide-ki Ishida、Masaya Fujita、Toshiyuki Inazu、Hideharu Ishida

  DOI：10.1055/s-2007-970766

  日期：2007.3

  A first chemical synthesis of GlcNAcβ(1→4)GlcUA-UDP is described here. This compound can be an essential tool to elucidate the catalytic mechanism of hyaluronic acid synthases (HAS) and this synthetic strategy contributes to the synthesis of ­various UDP-sugars which include modified GlcUA moieties.

  本文描述了GlcNAcβ(1→4)GlcUA-UDP的首次化学合成。这种化合物可以成为阐明透明质酸合成酶（HAS）催化机制的重要工具，这种合成策略有助于合成各种UDP糖，包括修饰的GlcUA部分。
• Synthesis of Tetrasaccharide Repeating Unit of the O‐Antigen from Enterohemorrhagic <i>Escherichia coli</i> O157 in the form of its 2‐(trimethylsilyl)ethyl Glycoside
  作者：Kakali Sarkar、Nirmolendu Roy

  DOI：10.1080/07328300500495878

  日期：2006.1.1

  Two alpha-linked disaccharide derivatives, ethyl 3,4,6-tri-O-acetyl-2-azido-2-deoxy-alpha-D-galactopyranosyl-(1 -> 2)-4-azido-3-O-benzyl-4,6-dideoxy-1-thio-alpha-D-mannopyranoside (10) and 2-(trimethylsilyl)ethyl 3-O-acetyl-4-O-benzoyl-2-O-benzyl-alpha-L-fucopyranosyl-(1 -> 4)-2,3-di-O-benzyl-6-O-tert-butyldiphenylsilyl-beta-D-glucopyranoside (16), were prepared from appropriate monosaccharide synthons. The disaccharide 16 was deacetylated and debenzoylated to afford the acceptor 17, which was allowed to react with the donor 10 to afford a tetrasaccharide derivative 18. This tetrasaccharide was transformed in three steps into 21, the desired repeating unit of the antigen from enterohemorrhagic E. coli type O157.
• A novel de-O-chloroacetylation reagent: 1-seleonocarbamoylpiperidine
  作者：Shingo Sogabe、Hiromune Ando、Mamoru Koketsu、Hideharu Ishihara

  DOI：10.1016/j.tetlet.2006.07.009

  日期：2006.9

  1-Selenocarbamoylpiperidine 2 chemoselectively cleaves the O-chloroacetyl group in the presence of other acyl groups such as acetyl, pivaloyl, and Fmoc without the assistance of a base. The high lipophilicity of 2 allowed us to use 1,4-dioxane, THF, and DMF as reaction solvents, thereby enabling dechloroacetylation at high temperature. A comparative experiment with other dechloroacetyl reagents showed that selenourea 2 has a high potential as a dechloroacetylation reagent. (c) 2006 Elsevier Ltd. All rights reserved.
• Restriction of Conformation in Galabiosides Via an <i>O</i>⁶−<i>O</i>²‘-Methylene Bridge
  作者：Michael Wilstermann、Joakim Balogh、Göran Magnusson

  DOI：10.1021/jo962371x

  日期：1997.5.1

  Treatment of 2-(trimethylsilyl)ethyl 2,3-di-O-acetyl-4-O-(3,4,6-tri-O-acetyl-alpha-D-galactopyranosyl)-beta-D-galactopyranoside (12) and 2-(trimethylsilyl)ethyl 2,3-di-O-benzyl-beta-D-glucopyranoside (15) with the novel reagent combination formaldehyde diphenylmercaptal-N-iodosuccinimide-trifluoromethanesulfonic acid [(PhS)(2)CH2/NIS/TfOH], gave the corresponding 6,2'-O- and 4,6-O-methylidene acetals 13 and 16 in 52% and 53% yield, respectively. Deacetylation of 13 gave 2-(trimethylsilyl)ethyl 4-O-alpha-D-galactopyranosyl-beta-D-galactopyranoside (1). The conformation of 1 was similar to that of the non-acetalated parent glycoside.