benzyl 2,3,4,6-tetra-O-trimethylsilyl-β-D-glucopyranoside | 18978-00-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzyl 2,3,4,6-tetra-O-trimethylsilyl-β-D-glucopyranoside
• 英文别名: Benzyl-2,O³,O⁴,O⁶-tetrakis-trimethylsilyl-β-D-glucopyranosid>；trimethyl-[(2R,3R,4S,5R,6R)-2-phenylmethoxy-3,5-bis(trimethylsilyloxy)-6-(trimethylsilyloxymethyl)oxan-4-yl]oxysilane
• CAS: 18978-00-2
• 化学式: C₂₅H₅₀O₆Si₄
• 分子量: 559.01
• InChiKey: QMOOUTBEWHHYJE-NHTNDUFYSA-N

物化性质

• 沸点：
  483.8±45.0 °C(Predicted)
• 密度：
  0.99±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.44
• 重原子数：
  35.0
• 可旋转键数：
  12.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  55.38
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  benzyl 2,3,4,6-tetra-O-trimethylsilyl-β-D-glucopyranoside 以 甲醇 、 溶剂黄146 、 丙酮 为溶剂， 反应 2.0h， 以75%的产率得到benzyl 2,3,4-tri-O-trimethylsilyl-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis and biological studies of glycosyl dopamine derivatives as potential antiparkinsonian agents

  摘要：

  A new approach to deliver dopamine into the central nervous system, based on the use of D-glucose as transportable agent, has been studied. Glycosyl dopamine derivatives bearing the sugar moiety linked to either the amino group or the catechol ring of dopamine through amide, eater or glycosidic bonds were synthesised as potential antiparkinsonian agents. Studies on the binding to dopamine D-2 receptor, in vitro stability, and locomotive effect in mice of the synthetic glycoconjugates are reported. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(00)00073-2
• 作为产物：
  描述：

  三甲基氯硅烷 、 苄基 alpha-D-吡喃葡萄糖苷 在 1,6-己二胺 作用下， 以 吡啶 为溶剂， 以74%的产率得到benzyl 2,3,4,6-tetra-O-trimethylsilyl-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis and biological studies of glycosyl dopamine derivatives as potential antiparkinsonian agents

  摘要：

  A new approach to deliver dopamine into the central nervous system, based on the use of D-glucose as transportable agent, has been studied. Glycosyl dopamine derivatives bearing the sugar moiety linked to either the amino group or the catechol ring of dopamine through amide, eater or glycosidic bonds were synthesised as potential antiparkinsonian agents. Studies on the binding to dopamine D-2 receptor, in vitro stability, and locomotive effect in mice of the synthetic glycoconjugates are reported. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(00)00073-2

文献信息

• Triterpenoid glycosides from Ladenbergia hexandra Klotzsch
  作者：Megumi Furukawa、Satoshi Kamo、Mitsuko Makino、Masahiro Kurita、Keiichi Tabata、Keiichi Matsuzaki、Takashi Suzuki、Taketo Uchiyama

  DOI：10.1016/j.phytochem.2017.01.014

  日期：2017.4

  From the bark of Ladenbergia hexandra Klotzsch, ten triterpenoid glycosides were isolated along with five known compounds, and their structures were determined based on extensive NMR and mass spectroscopic, GC and HPLC analyses. Some triterpenoid glycosides contained 6-deoxy-D-allose or D-allose as a sugar moiety. The absolute stereochemical assignment of the sugars was determined by comparison with

  从 Ladenbergia hexandra Klotzsch 的树皮中分离出 10 种三萜糖苷和 5 种已知化合物，并基于广泛的 NMR 和质谱、GC 和 HPLC 分析确定了它们的结构。一些三萜糖苷含有 6-脱氧-D-阿洛糖或 D-阿洛糖作为糖部分。糖的绝对立体化学归属是通过与合成样品的比较以及 GC 和 HPLC 分析来确定的。
• Direct Glycosylation of Bioactive Small Molecules with Glycosyl Iodide and Strained Olefin as Acid Scavenger
  作者：Xiangying Gu、Lin Chen、Xin Wang、Xiao Liu、Qidong You、Wenwei Xi、Li Gao、Guohua Chen、Yue-Lei Chen、Bing Xiong、Jingkang Shen

  DOI：10.1021/jo402551x

  日期：2014.2.7

  A new strategy for diversity-oriented direct glycosylation of bioactive small molecules was developed. This reaction features (-)-beta-pinene as acid scavenger and work with glycosyl iodides under mild conditions. With the aid of RP-HPLC and chiral SFC separation techniques, the new direct glycosylation proved effective at gram scale on bioactive small molecules including AZD6244, podophyllotoxin, paclitaxel, and docetaxel. Interesting glycoside derivatives were efficiently created with good yields and 1,2-cis selectivity.
• SCHWAB, WILFRIED;SCHELLER, GERHARD;SCHREIER, PETER, PHYTOCHEMISTRY, 29,(1990) N, C. 607-612
  作者：SCHWAB, WILFRIED、SCHELLER, GERHARD、SCHREIER, PETER

  DOI：——

  日期：——