benzyl 2,3,4,6-bis(di-O-isopropylidene)-α-D-mannopyranoside | 139722-11-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧吡喃
• 英文名称: benzyl 2,3,4,6-bis(di-O-isopropylidene)-α-D-mannopyranoside
• 英文别名: benzyl 2,3:4,6-di-O-isopropylidene-α-D-mannopyranoside；(1R,2S,6S,7S,9R)-4,4,12,12-tetramethyl-7-phenylmethoxy-3,5,8,11,13-pentaoxatricyclo[7.4.0.02,6]tridecane
• CAS: 139722-11-5；104477-36-3；117275-31-7；117275-32-8；117275-33-9
• 化学式: C₁₉H₂₆O₆
• 分子量: 350.412
• InChiKey: QNYVELBQGTXQGL-NRKLIOEPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  55.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  benzyl 2,3,4,6-bis(di-O-isopropylidene)-α-D-mannopyranoside 在 palladium on activated charcoal sodium hydroxide 、 氢气 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 96.0h， 生成 diethyl (2,3:4,6-di-O-isopropylidene-α-D-mannopyranosyl)methylphosphonate
  参考文献：
  名称：

  （4,6-di-O-膦酰基-β-d-甘露吡喃糖基）-甲基膦酸酯的合成及生物活性作为1l-肌醇1,4,5-三磷酸酯的类似物

  摘要：

  摘要由d-甘露糖合成了标题化合物（1）的α和β端基异构体。在关键步骤中，通过在两相条件下将受保护的甘露糖衍生物（8）与亚甲基双膦酸四乙酯直接Wadsworth-Emmons缩合制备甘露吡喃糖基磷酸酯的膦酸酯类似物。体外生物测定表明，β端基异构体（1a）是Ins（1,4,5）P 3 3-激酶的有效抑制剂，可抑制其他酶。

  DOI：

  10.1016/0008-6215(94)80020-0
• 作为产物：
  描述：

  甘露糖 在 对甲苯磺酸 、 乙酰氯 作用下， 以 丙酮 为溶剂， 反应 1.0h， 生成 benzyl 2,3,4,6-bis(di-O-isopropylidene)-α-D-mannopyranoside
  参考文献：
  名称：

  （4,6-di-O-膦酰基-β-d-甘露吡喃糖基）-甲基膦酸酯的合成及生物活性作为1l-肌醇1,4,5-三磷酸酯的类似物

  摘要：

  摘要由d-甘露糖合成了标题化合物（1）的α和β端基异构体。在关键步骤中，通过在两相条件下将受保护的甘露糖衍生物（8）与亚甲基双膦酸四乙酯直接Wadsworth-Emmons缩合制备甘露吡喃糖基磷酸酯的膦酸酯类似物。体外生物测定表明，β端基异构体（1a）是Ins（1,4,5）P 3 3-激酶的有效抑制剂，可抑制其他酶。

  DOI：

  10.1016/0008-6215(94)80020-0

文献信息

• Synthesis of (1-deoxy-4,6-O-bisphosphoryl-β-<scp>D</scp>-mannopyranosyl)methane phosphonate as an analogue of<scp>L</scp>-myo-inositol-1,4,5-trisphosphate
  作者：Sung-Kee Chung、Sung-Hwan Moon

  DOI：10.1039/c39920000077

  日期：——

  Synthesis of the α- and β-anomers of the title compound starting from D-mannose is reported.

  报道了从D-甘露糖合成标题化合物的α-和β-异构体。
• Cationic Palladium(II)-Catalyzed Stereoselective Glycosylation with Glycosyl Trichloroacetimidates
  作者：Jaemoon Yang、Colleen Cooper-Vanosdell、Enoch A. Mensah、Hien M. Nguyen

  DOI：10.1021/jo702436p

  日期：2008.2.1

  [GRAPHICS]The development of a new method for stereoselective glycosylation with glycosyl trichloroacetimidate donors employing cationic palladium(II), Pd(CH3CN)(4)(BF4)(2), is described. This process employs Pd(CH3CN)(4)(BF4)(2) as an efficient activator, providing access to a variety of disaccharides and glycopeptides. This reaction is highly stereoselective and proceeds under mild conditions with low catalyst loading. Interestingly, this palladium catalysis directs beta-glucosylations in the absence of classical neighboring group participation.
• Using In(III) as a promoter for glycosylation
  作者：Amanda L. Mattson、Anna K. Michel、Mary J. Cloninger

  DOI：10.1016/j.carres.2011.10.016

  日期：2012.1

  InCl3, InBr3, and In(OTf)(3) were tested as promoters in the preparation of glycosides from trichloroacetimidate precursors. A range of protecting groups and of alcohol acceptors were used to determine the versatility of these promoters. Disaccharide formation was demonstrated. In most cases, the In(III) compounds were shown to promote glycosylation better than the widely used promoter BF3 center dot OEt2. (C) 2011 Elsevier Ltd. All rights reserved.
• Yashunsky, Dmitry V.; Tsvetkov, Yury E.; Ferguson, Michael A.J., Journal of the Chemical Society. Perkin Transactions 1 (2001), 2002, vol. 2, # 2, p. 242 - 256
  作者：Yashunsky, Dmitry V.、Tsvetkov, Yury E.、Ferguson, Michael A.J.、Nikolaev, Andrei V.

  DOI：——

  日期：——
• Synthesis and biological activities of (4,6-di-O-phosphonato-β-d-mannopyranosyl)-methylphosphonate as an analogue of 1l-myo-inositol 1,4,5-trisphosphate
  作者：Sung-Kee Chung、Sung-Hwan Moon

  DOI：10.1016/0008-6215(94)80020-0

  日期：1994.7

  Abstract The synthesis of the α and β anomers of the title compound ( 1 ) was accomplished from d -mannose. In the key step, the phosphonate analogues of the mannopyranosyl phosphates were prepared by a direct Wadsworth-Emmons condensation of a protected mannose derivative ( 8 ) with tetraethyl methylenebisphosphonate under two-phase conditions. In vitro bioassays have shown that the β anomer ( 1a

  摘要由d-甘露糖合成了标题化合物（1）的α和β端基异构体。在关键步骤中，通过在两相条件下将受保护的甘露糖衍生物（8）与亚甲基双膦酸四乙酯直接Wadsworth-Emmons缩合制备甘露吡喃糖基磷酸酯的膦酸酯类似物。体外生物测定表明，β端基异构体（1a）是Ins（1,4,5）P 3 3-激酶的有效抑制剂，可抑制其他酶。