2,3,4,5-tetra-O-methyl-D-mannitol | 554433-80-6

• 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-tetra-O-methyl-D-mannitol
• 英文别名: 2,3,4,5-tetra-O-methyl-mannitol；(2R,3R,4R,5R)-2,3,4,5-tetramethoxyhexane-1,6-diol
• CAS: 554433-80-6
• 化学式: C₁₀H₂₂O₆
• 分子量: 238.281
• InChiKey: LUPLSCJPGNQYRS-ZYUZMQFOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.5
• 重原子数：
  16
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 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-tetra-O-methyl-D-mannitol 在 2-pentafluorophenyl-6,7-dihydro-5H-pyrrolo[2,1-c][1,2,4]triazol-2-ium tetrafluoroborate 、 吡啶 、 sodium tetrahydroborate 、 草酰氯 、 氢气 、 二甲基亚砜 、 三乙胺 、 palladium dichloride 作用下， 以 乙醇 、 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 34.92h， 生成 epi-Inositol
  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：

  2,3,4,5-tetra-O-methyl-1,6-di-O-trityl-D-mannitol 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 以77%的产率得到2,3,4,5-tetra-O-methyl-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

• Macrocyclic derivatives with a sucrose scaffold: insertion of a long polyhydroxylated linker between the terminal 6,6′-positions
  作者：Bartosz Chaciak、Kajetan Dąbrowa、Paweł Świder、Sławomir Jarosz

  DOI：10.1039/c8nj02808g

  日期：——

  A series of five new macrocyclic hybrids with a sucrose scaffold were prepared by the reaction of activated 1′,2,3,3′,4,4′-hexa-O-methylsucrose with diversely functionalized D-mannitols. The 21-, 25-, and 31-membered representatives containing mannitol units were prepared by a macrocyclization of 6,6′-di-O-propargylated sucrose with protected 1,6-diazido-D-mannitol or 6,6′-di-azidosucrose with propargylated

  通过活化的1'，2,3,3'，4,4'-六-O-甲基蔗糖与功能多样的D-甘露糖醇的反应制备了一系列五个新的具有蔗糖支架的大环杂种。含有甘露醇单元的21、25和31元代表是通过将6,6'-二-O-炔丙基蔗糖与受保护的1,6-二叠氮基-D-甘露醇或6,6'-di进行大环化制备的-叠氮蔗糖与炔丙基化的D-甘露醇（“点击”方法），而23位代表则通过1'，2,3,3'，4,4'-六-O-甲基-6的双N-烷基化制备1,6'-二氨基蔗糖与1,6-二溴酰基D-甘露醇。测试了所有蔗糖衍生物作为手性识别α-苯基乙铵（α-PEA）阳离子的假定宿主。在一种情况下，与我们先前报道的所有基于蔗糖的大环主体形成鲜明对比，观察到了R-对映体的意外反向偏好（K R / K S = 1.5）。
• 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.
• 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