1,6-di-O-trityl-2,3,4,5-tetra-O-benzyl-D-mannitol | 110578-67-1

• 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: 1,6-di-O-trityl-2,3,4,5-tetra-O-benzyl-D-mannitol
• 英文别名: [diphenyl-[(2R,3R,4R,5R)-2,3,4,5-tetrakis(phenylmethoxy)-6-trityloxyhexoxy]methyl]benzene
• CAS: 110578-67-1
• 化学式: C₇₂H₆₆O₆
• 分子量: 1027.31
• InChiKey: AQGGKZFFKJEJIP-VGUKHLMCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14.9
• 重原子数：
  78
• 可旋转键数：
  27
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.17
• 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：

  1,6-di-O-trityl-2,3,4,5-tetra-O-benzyl-D-mannitol 在 草酰氯 、 硫酸 、 二甲基亚砜 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 0.42h， 生成 2,3,4,5-tetra-O-benzyl-D-manno-hexodialdose
  参考文献：
  名称：

  Synthesis of cyclitols fused with a furoxan ring from alditols by intramolecular nitrile oxide dimerization

  摘要：

  通过将一种醛糖醇转化为双（醛肟），并进一步用N-氯丁二酰亚胺氧化肟基团至腈氧化物，这些腈氧化物自发地进行分子内二聚合形成呋罗环，实现了与呋罗环融合的环醇的合成。

  DOI：

  10.1039/a704208f
• 作为产物：
  描述：

  甘露醇 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 1,6-di-O-trityl-2,3,4,5-tetra-O-benzyl-D-mannitol
  参考文献：
  名称：

  Synthesis of cyclitols fused with a furoxan ring from alditols by intramolecular nitrile oxide dimerization

  摘要：

  通过将一种醛糖醇转化为双（醛肟），并进一步用N-氯丁二酰亚胺氧化肟基团至腈氧化物，这些腈氧化物自发地进行分子内二聚合形成呋罗环，实现了与呋罗环融合的环醇的合成。

  DOI：

  10.1039/a704208f

文献信息

• 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。
• NOVEL CROSSLINKING REAGENTS, MACROMOLECULES, THERAPEUTIC BIOCONJUGATES, AND SYNTHETIC METHODS THEREOF
  申请人：CellMosaic, Inc.

  公开号：US20150017246A1

  公开（公告）日：2015-01-15

  The invention provides novel chemical entities based on sugar alcohols. These new chemical entities are biocompatible and biodegradable. The molecules can be made in a single and pure form. The molecular weights of these molecules range from small (<1000 Da) to large (1000-120,000 Da). The sugar alcohol-based molecules can have functional groups throughout the molecule for crosslinking compounds, such as the preparation of antibody-drug conjugates, or to facilitate the delivery of therapeutic proteins, peptides, siRNA, and chemotherapeutic drugs. Also provided are new conjugate entities prepared through sugar alcohol molecules. Methods of synthesizing sugar alcohol-based molecules and conjugates are also within the scope of the invention.

  本发明提供了基于糖醇的新型化学物质。这些新型化学物质具有生物相容性和生物可降解性，分子可以制备成单一和纯净的形式。这些分子的分子量范围从小（<1000 Da）到大（1000-120000 Da）。基于糖醇的分子可以在整个分子中具有功能性基团，用于交联化合物，例如制备抗体药物偶联物，或促进治疗性蛋白质、肽、siRNA和化学治疗药物的传递。本发明还提供了通过糖醇分子制备的新型偶联实体。本发明还涉及合成基于糖醇的分子和偶联物的方法。
• NOVELCROSSLINKING REAGENTS, MACROMOLECULES, THERAPEUTIC CONJUGATES, AND SYNTHETIC METHODS THEREOF
  申请人：CellMosaic, Inc.

  公开号：US20140206903A1

  公开（公告）日：2014-07-24

  The invention provides novel chemical entities based on sugar alcohols. These new chemical entities are biocompatible and biodegradable. The molecules can be made in a single and pure form. The molecular weights of these molecules range from small (<1000 Da) to large (1000-120,000 Da). The sugar alcohol-based molecules can have functional groups throughout the molecule for crosslinking compounds, such as the preparation of antibody-drug conjugates, or to facilitate the delivery of therapeutic proteins, peptides, siRNA, and chemotherapeutic drugs. Also provided are new conjugate entities prepared through sugar alcohol molecules. Methods of synthesizing sugar alcohol-based molecules and conjugates are also within the scope of the invention.

  本发明提供了基于糖醇的新型化合物。这些新型化合物具有生物相容性和生物可降解性。这些分子可以以单一纯形式制备。这些分子的分子量范围从小分子（<1000 Da）到大分子（1000-120,000 Da）。基于糖醇的分子可以在整个分子中具有功能性基团，用于交联化合物，例如制备抗体药物偶联物，或促进治疗性蛋白质、肽、siRNA和化学治疗药物的传递。还提供了通过糖醇分子制备的新型偶联实体。本发明还涉及制备基于糖醇的分子和偶联物的方法。
• Crosslinking reagents, macromolecules, therapeutic conjugates, and synthetic methods thereof
  申请人：CellMosaic, Inc.

  公开号：US08907079B2

  公开（公告）日：2014-12-09

  The invention provides novel chemical entities based on sugar alcohols. These new chemical entities are biocompatible and biodegradable. The molecules can be made in a single and pure form. The molecular weights of these molecules range from small (<1000 Da) to large (1000-120,000 Da). The sugar alcohol-based molecules can have functional groups throughout the molecule for crosslinking compounds, such as the preparation of antibody-drug conjugates, or to facilitate the delivery of therapeutic proteins, peptides, siRNA, and chemotherapeutic drugs. Also provided are new conjugate entities prepared through sugar alcohol molecules. Methods of synthesizing sugar alcohol-based molecules and conjugates are also within the scope of the invention.

  本发明提供了基于糖醇的新型化学实体。这些新型化学实体具有生物相容性和生物降解性。这些分子可以制备成单一和纯净的形式。这些分子的分子量范围从小（<1000 Da）到大（1000-120,000 Da）。基于糖醇的分子可以在分子内具有功能性基团，用于交联化合物，例如制备抗体药物偶联物，或促进治疗性蛋白质、肽、siRNA和化疗药物的递送。还提供了通过糖醇分子制备的新型偶联实体。本发明还涉及合成基于糖醇的分子和偶联物的方法。
• 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.