(2R,3S,4R,5R,6S)-2,3,4,5-tetrakis(benzyloxy)-6-hydroxycyclohexanone | 1638491-15-2

• 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: (2R,3S,4R,5R,6S)-2,3,4,5-tetrakis(benzyloxy)-6-hydroxycyclohexanone
• 英文别名: (2R,3S,4R,5R,6S)-2,3,4,5-tetrabenzyloxy-6-hydroxycyclohexanone
• CAS: 1638491-15-2
• 化学式: C₃₄H₃₄O₆
• 分子量: 538.64
• InChiKey: NUMOLZHOBOVVSU-BRAMSPLKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.27
• 重原子数：
  40.0
• 可旋转键数：
  12.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  74.22
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (2R,3S,4R,5R,6S)-2,3,4,5-tetrakis(benzyloxy)-6-hydroxycyclohexanone 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 (3S,4R,5R)-2,2,3,4,5-pentakis(benzyloxy)cyclohexanone
  参考文献：
  名称：

  Nucleophilic Trapping of Alkoxy-Stabilized Oxyallyl Systems Generated from Inosose 2-O-Mesylates

  摘要：

  Protected inosose 2-O-mesylates generate oxyallyl systems by elimination of the mesylate group after enolization. The reaction is promoted by weak bases such as triethylamine and azide, and the oxyallyl systems are then trapped by nucleophilic alcohols or azide. Computations using DFT/B3LYP confirm that the singlet planar oxyallyl is stabilized by the exocyclic alkoxy group.

  DOI：

  10.1055/s-0034-1379490
• 作为产物：
  描述：

  2,3,4,5-tetra-O-methyl-1,6-di-O-trityl-D-mannitol 在 2-pentafluorophenyl-6,7-dihydro-5H-pyrrolo[2,1-c][1,2,4]triazol-2-ium tetrafluoroborate 、 吡啶 、 草酰氯 、 对甲苯磺酸 、 二甲基亚砜 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 35.92h， 生成 (2R,3S,4R,5R,6S)-2,3,4,5-tetrakis(benzyloxy)-6-hydroxycyclohexanone
  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

文献信息

• Site-selective benzoin-type cyclization of unsymmetrical dialdoses catalyzed by N-heterocyclic carbenes for divergent cyclitol synthesis
  作者：Bubwoong Kang、Yinli Wang、Satoru Kuwano、Yousuke Yamaoka、Kiyosei Takasu、Ken-ichi Yamada

  DOI：10.1039/c7cc01191a

  日期：——

  A highly site-selective NHC-catalyzed benzoin-type cyclization of unsymmetrical dialdoses was achieved.

  实现了高度对称的NHC催化的非对称拨号酶的安息香型环化。