2,3,4,5-tetra-O-methyl-1,6-di-O-trityl-D-mannitol | 554433-79-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 2,3,4,5-tetra-O-methyl-1,6-di-O-trityl-D-mannitol
• 英文别名: [diphenyl-[(2R,3R,4R,5R)-2,3,4,5-tetramethoxy-6-trityloxyhexoxy]methyl]benzene
• CAS: 554433-79-3
• 化学式: C₄₈H₅₀O₆
• 分子量: 722.921
• InChiKey: RHJQTNFWUJCYDX-AXRJLGSNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9
• 重原子数：
  54
• 可旋转键数：
  19
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.25
• 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：

  2,3,4,5-tetra-O-methyl-1,6-di-O-trityl-D-mannitol 在 草酰氯 、 对甲苯磺酸 、 二甲基亚砜 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 19.92h， 生成 (2S,3S,4S,5S)-2,3,4,5-tetramethoxyhexanedial
  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-(triphenylmethyl)-D-mannitol 、 碘甲烷 在 sodium hydroxide 作用下， 以 二甲基亚砜 为溶剂， 生成 2,3,4,5-tetra-O-methyl-1,6-di-O-trityl-D-mannitol
  参考文献：
  名称：

  D-甘露糖醇衍生的立体异构聚O-甲基[m，n]-聚氨酯

  摘要：

  使用D-甘露醇作为可再生的低成本起始原料成功制备了新型线性碳水化合物衍生的[ m，n ]-聚氨酯。关键的共聚单体1,6-二-O-苯基羰基-2,3,4,5-四-O-甲基-D-甘露醇与D-甘露醇合成的二胺或亚烷基二胺聚合而成。这些聚合反应分别提供了一种完全基于碳水化合物衍生物的[ 6,6 ]-聚氨酯，或由一个由聚-O-甲基取代的单元与一个聚亚甲基链交替组成的[ m，n ]-聚氨酯。由于C的存在，所有这些聚合物都是立体有规的2甘露糖醇的对称轴。光学活性聚氨酯通过标准方法（FTIR，RMN，GPC，TGA和DSC）进行表征。因此，GPC分析显示重均分子量在18,000和25,000 Da之间。热学研究（DSC）表明，所获得的聚合物是无定形材料，其T g值取决于二胺成分的结构和链长。©2012 Wiley Periodicals，Inc. J Polym Sci A部分：Polym Chem，2013年

  DOI：

  10.1002/pola.26406

文献信息

• Stereoregular poly-<i>O</i>-methyl [<i>m,n</i>]-polyurethanes derived from<scp>D</scp>-mannitol
  作者：Daniela M. Fidalgo、Adriana A. Kolender、Oscar Varela

  DOI：10.1002/pola.26406

  日期：2013.1.15

  Novel linear carbohydrate‐derived [m,n]‐polyurethanes are successfully prepared using D‐mannitol as renewable and low cost starting material. The key comonomer, 1,6‐di‐O‐phenylcarbonyl‐2,3,4,5‐tetra‐O‐methyl‐D‐mannitol is polymerized with a diamine synthesized from D‐mannitol or with alkylenediamines. These polymerization reactions afford, respectively, a [6,6]‐polyurethane entirely based on a carbohydrate

  使用D-甘露醇作为可再生的低成本起始原料成功制备了新型线性碳水化合物衍生的[ m，n ]-聚氨酯。关键的共聚单体1,6-二-O-苯基羰基-2,3,4,5-四-O-甲基-D-甘露醇与D-甘露醇合成的二胺或亚烷基二胺聚合而成。这些聚合反应分别提供了一种完全基于碳水化合物衍生物的[ 6,6 ]-聚氨酯，或由一个由聚-O-甲基取代的单元与一个聚亚甲基链交替组成的[ m，n ]-聚氨酯。由于C的存在，所有这些聚合物都是立体有规的2甘露糖醇的对称轴。光学活性聚氨酯通过标准方法（FTIR，RMN，GPC，TGA和DSC）进行表征。因此，GPC分析显示重均分子量在18,000和25,000 Da之间。热学研究（DSC）表明，所获得的聚合物是无定形材料，其T g值取决于二胺成分的结构和链长。©2012 Wiley Periodicals，Inc. J Polym Sci A部分：Polym Chem，2013年
• New derivatives of d-mannaric and galactaric acids.
  作者：Manuel Mancera、Isaac Roffé、Manuel Rivas、Juan A. Galbis

  DOI：10.1016/s0008-6215(03)00093-4

  日期：2003.5

  2.3.4 5 -Tetra-O-methyl-D-mannaric and galactaric acids and their bis(pentachlorophenyl) esters have been prepared as crystalline compounds, in good yields, from D-mannitol and galactitol, respectively. A new stereoregular polyamide, analogous to Nylon 66, has been prepared by polycondensation of bis(pentachlorophenyl) 2,3,4,5-tetra-O-methyl-D-mannarate with 1,6-diamino-1,6-dideoxy-2,3,4,5-tetra-O-methyl -D-mannitol dihydrochloride. The polymer has a M-w of 31,100 with a polydispersity of 1.5 (GPC). It was highly hygroscopic and soluble in ethanol, acetone, dimethyl sulfoxide, N,N-dimethylformamide and chloroform, but only slightly soluble in water. (C) 2003 Elsevier Science 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.