3-chloro-tri-O-benzyl-D-glucal | 71074-76-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-chloro-tri-O-benzyl-D-glucal
• 英文别名: 3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-5-chloro-3,4-dihydro-2H-pyran；2-chloroglucal；(2R,3R,4S)-5-chloro-3,4-bis(phenylmethoxy)-2-(phenylmethoxymethyl)-3,4-dihydro-2H-pyran
• CAS: 71074-76-5
• 化学式: C₂₇H₂₇ClO₄
• 分子量: 450.962
• InChiKey: RQSMVSXSBHFEGV-ZONZVBGPSA-N

物化性质

• 熔点：
  31-35 °C
• 沸点：
  547.9±50.0 °C(Predicted)
• 密度：
  1.22±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  32
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-chloro-tri-O-benzyl-D-glucal 在 乙醇 、 sodium 作用下， 以 氨 为溶剂， 反应 1.0h， 以74%的产率得到D-葡萄烯糖
  参考文献：
  名称：

  The lithiation of 2-chloroglucal derivatives

  摘要：

  Lithiation of 2-chloroglucal derivatives provides ready access to the corresponding 1-lithioglucals which undergo a variety of serve useful intermediates for further elaboration of the carbohydrate nucleus. Removal of the 2-chloro substituent may be affected using a Birch-type reduction. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.09.087
• 作为产物：
  描述：

  3,4,6-三苄氧基-D-葡萄烯糖 在 N-氯代丁二酰亚胺 、 silver nitrate 作用下， 以 乙腈 为溶剂， 反应 12.0h， 生成 3-chloro-tri-O-benzyl-D-glucal
  参考文献：
  名称：

  N-卤代琥珀酰亚胺/ AgNO 3-用于从甘油一步合成2-卤代糖的高效试剂系统：在通过Heck偶联反应合成2C支链糖中的应用

  摘要：

  已经开发出使用NIS / AgNO 3和NBS / AgNO 3作为试剂系统，由糖类方便地一步合成2-碘糖和2-溴糖的方法。这些2-卤代糖已通过Heck偶联反应转化为2C-支链的糖，证明了其实用性。三-O-乙酰基-2-碘代糖的费里尔反应，然后与丙烯酸甲酯进行Heck偶联反应，生成2C支链的O-糖苷。

  DOI：

  10.1021/ol500039s

文献信息

• Second generation benzannulation reactions: Sugar-derived Fischer chlorocarbene complexes in organic synthesis
  作者：Michael.R. Hallett、James E. Painter、Peter Quayle、Dean Ricketts、Prakash Patel

  DOI：10.1016/s0040-4039(98)00315-3

  日期：1998.4

  The facile metallation of 2-chloroglucal derivatives 8 and 11 affords ready access to the corresponding Fischer carbene complexes 10 and 13. Carbene complexes 10 and 13 undergo benzannulation reactions with acetylenes to provide functionalised benzopyrans in moderate overall yields.

  2-氯葡萄糖衍生物8和11的易金属化提供了对相应的Fischer卡宾配合物10和13的便捷访问。碳配合物10和13与乙炔进行苯并环化反应，以适中的总收率提供官能化的苯并吡喃。
• Highly diastereoselective 1,2-dichlorination of glycals using NCS/PPh3: study of substituent and solvent effects
  作者：Altaf Hussain、Debaraj Mukherjee

  DOI：10.1016/j.tet.2013.12.088

  日期：2014.2

  Highly diastereoselective 1,2-dichlorination of glycals has been achieved at room temperature conditions in good to excellent yields using a milder, more convenient, less hazardous reagent combination NCS/ PPh3 giving only one major product out of four possible diastereomers [either alpha-gluco (2) or alpha-manno (4)] depending upon the substituents. The diastereoselectivity is maximum (100% alpha/beta-selectivity as well as cis/trans selectivity) for D-galactal and L-rhamnal derivatives. Detailed studies showed that solvent and substituent effects play a significant role in determining the product distribution. (C) 2014 Elsevier Ltd. All rights reserved.
• <i>N</i>-Halosuccinimide/AgNO₃-Efficient Reagent Systems for One-Step Synthesis of 2-Haloglycals from Glycals: Application in the Synthesis of 2C-Branched Sugars via Heck Coupling Reactions
  作者：Suresh Dharuman、Yashwant D. Vankar

  DOI：10.1021/ol500039s

  日期：2014.2.21

  one-step synthesis of 2-iodoglycals and 2-bromoglycals from glycals using NIS/AgNO3 and NBS/AgNO3 as reagent systems has been developed. The utility of these 2-haloglycals has been demonstrated by converting them into 2C-branched glycals via the Heck coupling reaction. Ferrier reaction of tri-O-acetyl-2-iodoglycals followed by Heck coupling reaction with methyl acrylate leads to 2C-branched O-glycosides

  已经开发出使用NIS / AgNO 3和NBS / AgNO 3作为试剂系统，由糖类方便地一步合成2-碘糖和2-溴糖的方法。这些2-卤代糖已通过Heck偶联反应转化为2C-支链的糖，证明了其实用性。三-O-乙酰基-2-碘代糖的费里尔反应，然后与丙烯酸甲酯进行Heck偶联反应，生成2C支链的O-糖苷。
• The lithiation of 2-chloroglucal derivatives
  作者：Ewan Boyd、Michael R. Hallett、Ray V.H. Jones、James E. Painter、Prakash Patel、Peter Quayle、Anita J. Waring (née Potts)

  DOI：10.1016/j.tetlet.2006.09.087

  日期：2006.11

  Lithiation of 2-chloroglucal derivatives provides ready access to the corresponding 1-lithioglucals which undergo a variety of serve useful intermediates for further elaboration of the carbohydrate nucleus. Removal of the 2-chloro substituent may be affected using a Birch-type reduction. (c) 2006 Elsevier Ltd. All rights reserved.