Tetrakis-(3-bromo-propyl)-silane | 850883-22-6

• 分子结构分类: 有机化合物 - 有机盐 - 有机金属盐
• 英文名称: Tetrakis-(3-bromo-propyl)-silane
• 英文别名: Silane, tetrakis(3-bromopropyl)-；tetrakis(3-bromopropyl)silane
• CAS: 850883-22-6
• 化学式: C₁₂H₂₄Br₄Si
• 分子量: 516.024
• InChiKey: KTBPOOFLBREMIO-UHFFFAOYSA-N

物化性质

• 沸点：
  407.9±45.0 °C(Predicted)
• 密度：
  1.637±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.58
• 重原子数：
  17
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  2-acetamido-3,4,6-tri-O-acetyl-1-S-acetyl-2-deoxy-1-thio-β-D-glucopyranose 、 Tetrakis-(3-bromo-propyl)-silane 在 CSA 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 2.0h， 以94%的产率得到
  参考文献：
  名称：

  Synthesis of sialyllactosamine clusters using carbosilane as core scaffolds by means of chemical and enzymatic approaches

  摘要：

  An efficient synthesis of sialyllactosamine (SiaLacNAc) clusters using carbosilanes as core scaffolds has been accomplished by means of chemical and enzymatic approaches. N-Acetyl-D-glucosamine (GlcNAc) clusters having O-glycosidic linkage or S-glycosidic linkage were chemically synthesized from known intermediates in high yields. The GlcNAc clusters were first used as substrates for beta 1,4 galactosyl transferase using UDP-galactose (UDP-Gal) as a sugar source to provide corresponding N-acetyllactosamine clusters. Further sugar elongation of the LacNAc clusters was demonstrated using alpha 2,3 sialyl transferase and CMP-neuraminic acid (CMP-NANA) to yield the corresponding SiaLacNAc clusters. (c) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.06.066

文献信息

• Systematic syntheses of influenza neuraminidase inhibitors: A series of carbosilane dendrimers uniformly functionalized with thioglycoside-type sialic acid moieties
  作者：Jun-Ichi Sakamoto、Tetsuo Koyama、Daisei Miyamoto、Sangchai Yingsakmongkon、Kazuya I.P.J. Hidari、Wipawee Jampangern、Takashi Suzuki、Yasuo Suzuki、Yasuaki Esumi、Takemichi Nakamura、Ken Hatano、Daiyo Terunuma、Koji Matsuoka

  DOI：10.1016/j.bmc.2009.06.036

  日期：2009.8

  and 12-functionalized dendrimers, and in linkage patterns, such as normal aliphatic linkage, ether- and amide-linkages. Biological evaluations of these glycodendrimers showed that all of the ether- and amide-elongated compounds had inhibitory potencies for the influenza sialidases in the mM range, while compounds having normal aliphatic linkage did not have any activities except for a 12-functionalized

  为了开发新型流感唾液酸酶抑制剂，我们构建了糖簇库，该糖簇由十二种具有硫糖苷键的唾液酸化树枝状大分子组成，可抵抗唾液酸酶的水解。通过唾液酸经乙酰基修饰的糖苷配基在糖苷配基末端改性的硫代唾液酸苷与十二种具有溴化末端的碳硅烷树状大分子在脱乙酰基条件下的缩合反应合成了这些唾液酸树枝状酯，并进行了暂时的重新保护以进行纯化。通过酯交换作用和随后的皂化作用来除去对糖类树状聚合物的所有保护，从而以良好的产率提供相应的水溶性糖类树状聚合物。为了研究结构与活动的关系，树枝状大分子支架，其中糖部分的数目不同，例如3-，4-，6-和12-官能化树枝状大分子，并且在连接方式上不同，例如正常的脂族连接，醚-和酰胺-连接。这些糖类树状大分子的生物学评估表明，所有醚和酰胺延长的化合物都对mN范围的唾液酸流感病毒具有抑制作用，而具有正常脂族键的化合物除12-官能化化合物外没有任何活性。
• Synthesis of carbosilane dendrimers having peripheral mannose and mannobiose
  作者：Tomonori Mori、Ken Hatano、Koji Matsuoka、Yasuaki Esumi、Eric J. Toone、Daiyo Terunuma

  DOI：10.1016/j.tet.2005.01.090

  日期：2005.3

  The mannose monosaccharide derivative, acetylthiopropyl 2,3,4,6-tetra-O-acetyl-alpha-D-mannopyranoside (Man), and the mannobiose derivative, acetylthiopropyl 2,4,6-tri-O-acetyl-3-O-(2,3',4',6'-tetra-O-acetyl-alpha-D-mannopyranosyl)-alpha-D-mannopyranoside (alpha-1,3-Man), were synthesized respectively. These mannose derivatives were introduced into carbosilane dendrimer scaffolds of the zero and first generations. As a result, six carbosilane dendrimers were functionalized by Man and alpha-1,3-Man. Isothermal titration microcalorimetry was done to determine binding assay between mannose moieties of carbosilane dendrimer and concanavalin A. It was found that carbosilane dendrimers bound more efficiently to concanavalin A than free mannose (Me-alpha-Man) and mannobiose (Me-alpha-1,3-' Man). (c) 2005 Elsevier Ltd. All rights reserved.
• Lactotriaose-containing carbosilane dendrimers: Syntheses and lectin-binding activities
  作者：Akihiro Yamada、Ken Hatano、Tetsuo Koyama、Koji Matsuoka、Naonori Takahashi、Kazuya I.P.J. Hidari、Takashi Suzuki、Yasuo Suzuki、Daiyo Terunuma

  DOI：10.1016/j.bmc.2006.12.030

  日期：2007.2

  Carbosilane dendrimers periphery-functionalized with lactotriaose (GlcNAc beta 1-3Gal beta l-4Glc) with valencies of three, four, six, and twelve were prepared for use in a lectin-binding assay. A lactotriaose derivative was prepared from D-glucosamine and D-lactose derivatives. The N-Troc-protected glucosamine glycosyl donor and 3'-O-unprotected lactose glycosyl acceptor were condensed in the presence of silver trifluoromethanesulfonate and methylsulfenyl bromide to provide corresponding trisaccharide with new beta-1-3 linkages in 92% yield. The protection group of the trisaccharide was transformed into an acetyl group. The 4-pentenyl glycoside was prepared from the acetate via glycosyl bromide. The alkene was converted into acetyl sulfide by addition of thioacetic acid under radical conditions. The lactotriaose unit was linked with carbosilane dendrimers to afford acelyl-protected glycodendrimers. De-O-acetylation of the dendrimers was carried out in the presence of sodium methoxide and then aq NaOH to give the desired lactotriaose clusters using a carbosilane dendrimer backbone. Their biological activities toward WGA were evaluated by fluorescence methods. The binding constants of free lactotriaose and trivalent, tetravalent, hexavalent, and dodecavalent glycodendrimers to WGA were determined to be 1.1 x 10(3), 4.4 x 10(4), 5.1 x 10(4), 2.8 x 10(6), and 1.3 x 10(6) M-1, respectively. The hexavalent glycodendrimer showed a 2500-fold larger binding effect than that of free lactotriaose. (c) 2006 Elsevier Ltd. All rights reserved.
• Sialyl α(2 → 3) lactose clusters using carbosilane dendrimer core scaffolds as influenza hemagglutinin blockers
  作者：Hiroyuki Oka、Tomotsune Onaga、Tetsuo Koyama、Chao-Tan Guo、Yasuo Suzuki、Yasuaki Esumi、Ken Hatano、Daiyo Terunuma、Koji Matsuoka

  DOI：10.1016/j.bmcl.2008.06.101

  日期：2008.8

  An efficient synthesis of a series of carbosilane dendrimers uniformly functionalized with sialyl alpha(2 -> 3) lactose (Neu5Ac alpha(2 -> 3)Gal beta(1 -> 4)Glc beta 1 ->) moieties was accomplished. The results of a preliminary study on biological responses against influenza virus hemagglutinin, using the sialyl lactose clusters showed unique biological activities on the basis of the structure-activity relationship according to the carbosilane scaffolds. (c) 2008 Elsevier Ltd. All rights reserved.
• Thiosialoside clusters using carbosilane dendrimer core scaffolds as a new class of influenza neuraminidase inhibitors
  作者：Jun-Ichi Sakamoto、Tetsuo Koyama、Daisei Miyamoto、Sangchai Yingsakmongkon、Kazuya I.P.J. Hidari、Wipawee Jampangern、Takashi Suzuki、Yasuo Suzuki、Yasuaki Esumi、Ken Hatano、Daiyo Terunuma、Koji Matsuoka

  DOI：10.1016/j.bmcl.2006.10.085

  日期：2007.2

  An efficient synthesis of a series of carbosilane dendrimers uniformly functionalized with alpha-thioglycoside of sialic acid was accomplished. The results of a preliminary study on biological responses against influenza virus sialidases using thiosialoside clusters showed that some of the glycodendrimers have inhibitory potencies against the sialidases. (c) 2006 Elsevier Ltd. All rights reserved.