2-(((2S,3R,4S,5S,6R)-3,4,5-triacetoxy-6-(acetoxymethyl)tetrahydro-2H-pyran-2-yl)oxy)acetic acid | 698350-16-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-(((2S,3R,4S,5S,6R)-3,4,5-triacetoxy-6-(acetoxymethyl)tetrahydro-2H-pyran-2-yl)oxy)acetic acid
• 英文别名: carboxymethyl-2,3,4,6-tetra-O-acetyl-α-D-galactopyranoside；2-[(2S,3R,4S,5S,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyacetic acid
• CAS: 698350-16-2
• 化学式: C₁₆H₂₂O₁₂
• 分子量: 406.343
• InChiKey: TWWYGXIQWBPJMT-CHUNWDLHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  28
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  161
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  2-(((2S,3R,4S,5S,6R)-3,4,5-triacetoxy-6-(acetoxymethyl)tetrahydro-2H-pyran-2-yl)oxy)acetic acid 在 吡啶 、 甲醇 、 水 作用下， 反应 30.0h， 生成 carboxymethyl-3,4,6-tri-O-acetyl-α-D-galactopyranoside-2-O-lactone
  参考文献：
  名称：

  羧甲基糖苷内酯（CMGLs）：碳水化合物部分的结构变异

  摘要：

  从烯丙基糖苷合成具有异头构型，保护基团（乙酰基或苄基）和呋喃糖基或吡喃糖基环的新的基于葡萄糖和半乳糖的双环内酯，并将其用于制备一系列新的糖基化炔烃酰胺。

  DOI：

  10.1016/j.tetasy.2007.09.007
• 作为产物：
  描述：

  2,3,4,6-tetra-O-acetyl-1-O-allyl-α-D-galactopyranoside 在 ruthenium trichloride sodium periodate 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 2.0h， 以95%的产率得到2-(((2S,3R,4S,5S,6R)-3,4,5-triacetoxy-6-(acetoxymethyl)tetrahydro-2H-pyran-2-yl)oxy)acetic acid
  参考文献：
  名称：

  羧甲基糖苷内酯（CMGLs）：碳水化合物部分的结构变异

  摘要：

  从烯丙基糖苷合成具有异头构型，保护基团（乙酰基或苄基）和呋喃糖基或吡喃糖基环的新的基于葡萄糖和半乳糖的双环内酯，并将其用于制备一系列新的糖基化炔烃酰胺。

  DOI：

  10.1016/j.tetasy.2007.09.007

文献信息

• Synthesis of new mono- and disaccharidic carboxymethylglycoside lactones (CMGLs) and their use toward 1,2-bisfunctionalized carbohydrate synthons
  作者：Rouba Cheaib、Arkadiusz Listkowski、Stéphane Chambert、Alain Doutheau、Yves Queneau

  DOI：10.1016/j.tetasy.2008.07.016

  日期：2008.8

  A general and convenient access to mono- and disaccharidic carboxymethyl glycoside lactones (CMGLs) is described. By taking advantage of the free OH at the 2-position, obtained after the opening of CMGLs by amines, the synthesis of a series of new 1,2-bisfunctionalized carbohydrate synthons is reported.

  描述了单和二糖基羧甲基糖苷内酯（CMGLs）的一般和方便访问。通过利用由胺打开CMGL之后在2-位获得的游离OH，报道了一系列新的1,2-双官能化碳水化合物合成子的合成。
• Process for the production of peracylated 1-0-glycosides
  申请人：Schering AG

  公开号：US20030069402A1

  公开（公告）日：2003-04-10

  The invention relates to a process for the production of peracylated 1-O-glycosides of general formula I or salts thereof 1 in which sugar is a monosaccharide that is functionalized in 1-OH-position, R represents methyl, ethyl, propyl, isopropyl, tbutyl, phenyl, n means 2, 3 or 4, X means —COO— or —NH—and L means a straight-chain, branched, saturated or unsaturated C 1 -C 30 carbon chain, which optionally is interrupted or substituted by groups. The process according to the invention starts from economical starting materials, provides good yields and allows the production of peracylated saccharides with 1-O-functionalized side chains on an enlarged scale.

  该发明涉及一种生产通式I的过酰化1-O-糖苷或其盐的工艺，其中糖是在1-OH位置上被官能化的单糖，R代表甲基、乙基、丙基、异丙基、叔丁基、苯基，n取2、3或4，X代表—COO—或—NH—，L代表一条直链、分支、饱和或不饱和的C1-C30碳链，该碳链可以被基团中断或取代。根据该发明的工艺从经济实惠的起始材料开始，提供良好的产量，并允许在扩大规模上生产具有1-O官能化侧链的过酰化糖苷。
• Indium salts-catalyzed O and S-glycosylation of bromo sugar with benzyl glycolate: an unprecedented hydrogenolysis
  作者：Sunena Chandra、Ram N. Yadav、Armando Paniagua、Bimal K. Banik

  DOI：10.1016/j.tetlet.2016.02.039

  日期：2016.3

  and S-glycosyl esters and their corresponding acids are synthesized through a reaction of bromo sugar and benzyl glycolate in the presence of indium trichloride and indium tribromide as promoter. We discovered unprecedented catalytic effects of indium tribromide in glycosylation and hydrogenolysis in a one-pot operation. The sugar acid is a potential chiral auxiliary for the synthesis of biologically

  在三氯化铟和三溴化铟作为促进剂的存在下，通过溴糖和羟基乙酸苄酯的反应合成了各种O和S-糖基酯及其相应的酸。我们发现一锅操作中三溴化铟在糖基化和氢解中具有空前的催化作用。糖酸是合成各种兴趣的生物活性化合物的潜在手性助剂。
• Multivalent Nanofibers of a Controlled Length: Regulation of Bacterial Cell Agglutination
  作者：Dong-Woo Lee、Taehoon Kim、Il-Soo Park、Zhegang Huang、Myongsoo Lee

  DOI：10.1021/ja306802m

  日期：2012.9.12

  Control of the size and shape of molecular assemblies on the nanometer scale in aqueous solutions is very important for the regulation of biological functions. Among the well-defined supramolecular structures of organic amphiphiles, one-dimensional nanofibers have attracted much attention because of their potential applications in biocompatible materials. Although much progress has been made in the field of self-assembled nanofobers, the ability to control the fiber length remains limited. The approach for control of the fiber length presented herein overcomes this limitation through the coassembly of amphiphilic rod-coil molecules in which the crystallinity of the aromatic segment can be regulated by pi-pi stacking interactions. The introduction of carbohydrate segments into the fiber exterior endows the nanofibers with the ability to adhere to bacterial cells. Notably, the fiber length systematically regulates the agglutination and proliferation of bacterial cells exposed to these fibers.
• Efficient preparation of carbohydrate- and related polyol-amphiphiles by hydrazone ligation
  作者：Cyrille Grandjean、Valérie Santraine、Nathalie Fardel、Ange Polidori、Bernard Pucci、Hélène Gras-Masse、Dominique Bonnet

  DOI：10.1016/j.tetlet.2004.03.011

  日期：2004.4

  The hydrazone ligation can be used to couple clustered-glycosides or glycomimetics functionalized with a hydrazino group with lipophilic glyoxylyl acid derivatives to give the corresponding amphiphiles in high yield and purity. (C) 2004 Elsevier Ltd. All rights reserved.