2,3,4,5-tetrakis-benzyloxyhexane-1,6-diol | 256342-73-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 2,3,4,5-tetrakis-benzyloxyhexane-1,6-diol
• 英文别名: 2,3,4,5-tetrakis-O-benzyl-D-galactitol；2,3,4,5-tetra-O-benzyl-galactitol；(2R,3S,4R,5S)-2,3,4,5-tetrakis(phenylmethoxy)hexane-1,6-diol
• CAS: 256342-73-1
• 化学式: C₃₄H₃₈O₆
• 分子量: 542.672
• InChiKey: WORRLZMALIWGPN-XDPXVBSOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  40
• 可旋转键数：
  17
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 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：

  2,3,4,5-tetrakis-benzyloxyhexane-1,6-diol 在 2-pentafluorophenyl-6,7-dihydro-5H-pyrrolo[2,1-c][1,2,4]triazol-2-ium tetrafluoroborate 、 sodium tetrahydroborate 、 草酰氯 、 二甲基亚砜 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙醇 、 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 18.92h， 生成 (1R,2S,3R,4R,5R,6R)-3,4,5,6-tetrakis(benzyloxy)cyclohexane-1,2-diol
  参考文献：
  名称：

  Synthesis of allo- and epi-Inositol via the NHC-Catalyzed Carbocyclization of Carbohydrate-Derived Dialdehydes

  摘要：

  A synthesis of carbocyclic sugars from carbohydrate-derived dialdehydes using organocatalysis has been developed. Sorbitol, mannitol, and galactitol were converted via 1,6-tritylation, perbenzylation or permethylation, detritylation, and Swern oxidation into 2,3,4,5-tetra-O-alkyl-dialdoses that were cyclized via the benzoin reaction promoted by a triazolium carbene. Manno- and galacto-configured dialdehydes gave predominantly single inosose stereoisomers in up to 75% yield if the mixture was acetylated prior to isolation while the gluco-dialdehyde afforded a mixture of three stereoisomers in 61% overall yield. The inososes were stereospecifically reduced using sodium borohydride and then deprotected to give allo- and epi-inositol in good yield that confirmed the structural and stereochemical assignments.

  DOI：

  10.1021/jo500645z
• 作为产物：
  描述：

  1,6-di-O-trityl-galactitol 在 甲醇 、 硫酸 、 sodium hydride 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 25.0h， 生成 2,3,4,5-tetrakis-benzyloxyhexane-1,6-diol
  参考文献：
  名称：

  A straightforward synthesis of perbenzylated conduritols from alditols by ring closing olefin metathesis

  摘要：

  通过将半乳糖醇、D-甘露醇和D-葡萄糖醇正式转化为相应的末端二烯，随后进行环闭合烯烃复分解反应，实现了苯甲酰化康杜利托醇A、E和F的六步合成。

  DOI：

  10.1039/a906626h

文献信息

• Ruthenium Carbene Complexes with Imidazol-2-ylidene Ligands: Syntheses of Conduritol Derivatives Reveals Superior RCM Activity
  作者：Lutz Ackermann、David El Tom、Alois Fürstner

  DOI：10.1016/s0040-4020(99)01102-3

  日期：2000.4

  Syntheses of conduritol A, E and F derivatives are described using galactitol, d-mannitol and d-glucitol, respectively, as the starting materials. The key steps of this approach comprise a Tebbe olefination reaction for the preparation of dienes 15, 21 and 27 followed by ring closing metathesis (RCM) for the formation of the polyhydroxylated cyclohexene rings of the targets. A comparative study shows

  描述了分别使用半乳糖醇，d-甘露糖醇和d-葡萄糖醇作为起始原料的conduritol A，E和F衍生物的合成。这种方法的关键步骤包括用于二烯的制备将Tebbe烯化反应15，21和27，随后通过闭环复分解（RCM）为靶的多羟基化的环己烯环的形成。一项比较研究表明，在催化范围内带有催化量的钌卡宾配合物3a的催化量最佳，后者带有一个PCy 3和一个2,3-二氢-1 H-咪唑-2-亚烷基配体。
• Convenient one-pot synthesis of thiosugars and their efficient conversion to polyoxygenated cycloalkenes
  作者：Jingjing Zhang、Youhong Niu、Xiaoping Cao、Xin-Shan Ye

  DOI：10.1016/j.tet.2012.03.086

  日期：2012.6

  A convenient synthesis of polyoxygenated tetrahydrothiopyrans and thiepanes from various alditol derivatives with xylo, ribo, manno, gluco, galacto, and fuco configurations is described. The preparation started from the corresponding partially protected alditols and proceeded in a 'one-pot' manner to afford the final products in 80%-95% yield. Furthermore, thiosugar compounds 2b, 2d, and 2g were converted to the optically pure polyoxygenated cycloalkenes through Ramberg-Backlund reaction in moderate to good overall yield. The procedures can be used for the preparation of polyoxygenated thiosugars and cycloalkenes on a relatively large scale. (C) 2012 Elsevier Ltd. All rights reserved.
• Synthesis of <i>allo</i>- and <i>epi</i>-Inositol via the NHC-Catalyzed Carbocyclization of Carbohydrate-Derived Dialdehydes
  作者：Kieran P. Stockton、Ben W. Greatrex、Dennis K. Taylor

  DOI：10.1021/jo500645z

  日期：2014.6.6

  A synthesis of carbocyclic sugars from carbohydrate-derived dialdehydes using organocatalysis has been developed. Sorbitol, mannitol, and galactitol were converted via 1,6-tritylation, perbenzylation or permethylation, detritylation, and Swern oxidation into 2,3,4,5-tetra-O-alkyl-dialdoses that were cyclized via the benzoin reaction promoted by a triazolium carbene. Manno- and galacto-configured dialdehydes gave predominantly single inosose stereoisomers in up to 75% yield if the mixture was acetylated prior to isolation while the gluco-dialdehyde afforded a mixture of three stereoisomers in 61% overall yield. The inososes were stereospecifically reduced using sodium borohydride and then deprotected to give allo- and epi-inositol in good yield that confirmed the structural and stereochemical assignments.
• A straightforward synthesis of perbenzylated conduritols from alditols by ring closing olefin metathesis
  作者：John K. Gallos、Theocharis V. Koftis、Vassiliki C. Sarli、Konstantinos E. Litinas

  DOI：10.1039/a906626h

  日期：——

  The synthesis of perbenzylated conduritols A, E and F has been achieved in six steps by formal conversion of galactitol, D-mannitol and D-glucitol into the respective terminal dienes, followed by ring closing olefin metathesis.

  通过将半乳糖醇、D-甘露醇和D-葡萄糖醇正式转化为相应的末端二烯，随后进行环闭合烯烃复分解反应，实现了苯甲酰化康杜利托醇A、E和F的六步合成。