n-octyl 2,3,5,6-tetra-O-benzoyl-β-D-galactofuranoside | 417717-54-5

• 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: n-octyl 2,3,5,6-tetra-O-benzoyl-β-D-galactofuranoside
• 英文别名: octyl 2,3,5,6-tetra-O-benzoyl-β-D-galactofuranoside
• CAS: 417717-54-5
• 化学式: C₄₂H₄₄O₁₀
• 分子量: 708.805
• InChiKey: JYCWQTQROOJUNU-FIGOLCKWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.62
• 重原子数：
  52.0
• 可旋转键数：
  18.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  123.66
• 氢给体数：
  0.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  n-octyl 2,3,5,6-tetra-O-benzoyl-β-D-galactofuranoside 在 硫酸 、 氢溴酸 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 反应 6.17h， 生成
  参考文献：
  名称：

  含半呋喃呋喃糖基的荧光染料的合成及生物学性质

  摘要：

  合成了两种荧光半乳糖呋喃糖苷，并对未感染和利什曼原虫感染的巨噬细胞评估了它们的生物学活性。两个标记的支架都能够穿透巨噬细胞。与作为参考的母体辛基半乳糖呋喃糖苷的活性相比，荧光素结合物显示出改变的生物学特性，而若丹明6G与脂质链协同作用以显着增加抗寄生虫活性。

  DOI：

  10.1016/j.bmcl.2016.11.090
• 作为产物：
  描述：

  苯甲酰氯 、 octyl β-D-galactofuranoside 在 吡啶 作用下， 生成 n-octyl 2,3,5,6-tetra-O-benzoyl-β-D-galactofuranoside
  参考文献：
  名称：

  含半呋喃呋喃糖基的荧光染料的合成及生物学性质

  摘要：

  合成了两种荧光半乳糖呋喃糖苷，并对未感染和利什曼原虫感染的巨噬细胞评估了它们的生物学活性。两个标记的支架都能够穿透巨噬细胞。与作为参考的母体辛基半乳糖呋喃糖苷的活性相比，荧光素结合物显示出改变的生物学特性，而若丹明6G与脂质链协同作用以显着增加抗寄生虫活性。

  DOI：

  10.1016/j.bmcl.2016.11.090

文献信息

• Synthesis of Galactofuranose-Containing Acceptor Substrates for Mycobacterial Galactofuranosyltransferases
  作者：Gladys C. Completo、Todd L. Lowary

  DOI：10.1021/jo800457j

  日期：2008.6.1

  solvent led to the formation Galf glycosides contaminated with no pyranoside isomer, thus allowing the efficient preparation of furanoside derivatives of this monosaccharide. The synthesis of disaccharide targets 1, 2, 11 and 12 proceeded without difficulty through the use of thioglycoside donors and octyl glycoside acceptors, both carrying benzoyl protection. In the synthesis of the tri- and tetrasaccharides

  结核分支杆菌感染的细胞壁的主要结构成分是分支霉菌基-阿拉伯半乳聚糖（MAG）。这种大的糖结合物，其核心〜30的骨架d -galactofuranose（加˚F），其是通过含有连接体的二糖的方式连接于肽聚糖残基升鼠李糖和2-乙酰胺基-2-脱氧d葡萄糖。最近的研究支持了半乳聚糖生物合成的模型，其中整个结构是通过两种双功能的半乳糖醛酸糖基转移酶的作用而组装而成的。这些生物化学研究能够成为可能，部分地通过访问MAG的寡糖片段的面板络合物（1 -12），我们在这里描述其综合。这项研究的早期关键发现是，在乙醇溶剂存在下，碘促进的半乳糖二乙基二硫缩醛的环化反应（19）导致形成没有被吡喃糖苷异构体污染的Gal f糖苷，从而可以有效地制备呋喃糖苷的呋喃糖苷衍生物。这种单糖。的二糖目标的合成1，2，11和12通过使用硫糖苷给体的过程没有任何困难和辛基糖苷受体，既携带苯甲酰保护。在三-和四糖的合成3 - 6，我
• 6-Deoxy-6-fluoro galactofuranosides: regioselective glycosylation, unexpected reactivity, and anti-leishmanial activity
  作者：Jeane Vaugenot、Abderrafek El Harras、Olivier Tasseau、Rémi Marchal、Laurent Legentil、Boris Le Guennic、Thierry Benvegnu、Vincent Ferrières

  DOI：10.1039/c9ob02596k

  日期：——

  Standard glycosylation of unprotected 6-fluorogalactofuranoside turned to three competitive reactions and afforded difuranosides able to impact growth of Leishmania tarentolae.

  不保护的6-氟半乳糖苷的标准糖基化转化为三个竞争反应，并得到能够影响蜥蜴利什曼原虫生长的二氧杂环糖苷。
• A NEW APPROACH TO A DISACCHARIDIC HAPTEN CONTAINING A GALACTOFURANOSYL ENTITY
  作者：Vincent Ferrières、Myriam Roussel、Muriel Gelin、Daniel Plusquellec

  DOI：10.1081/car-100108662

  日期：2001.12.31

  A short synthetic entry into the disaccharidic hapten beta-D-Galf-(1-->3)-alpha-D-Manp-O(CH2)(8)CO2Me containing a galactofuranosyl entity at the non-reducing part is described. The synthetic scheme was designed in such a way that each required building block could be obtained by minimizing the number of chemical and purification steps. Indeed, compound 8 was obtained according to a four step-one pot preparation.
• Synthesis of the lipoteichoic acid of the Streptococcus species DSM 8747
  作者：Yan Qiao、Buko Lindner、Ulrich Zähringer、Peter Truog、Richard R. Schmidt

  DOI：10.1016/j.bmc.2010.04.006

  日期：2010.6.1

  The lipoteichoic acid (LTA) of the Streptococcus species DSM 8747 consists of a beta-D-galactofuranosyl diacylglycerol moiety (with different acyl groups) that is linked via 6-O to a poly(glycerophosphate) backbone; about 30% of the glycerophosphate moieties carry at 2-O hydrolytically labile D-alanyl residues. As typical LTA for this array of compounds LTA 1a was synthesized. To this end, from D-galactose the required galactofuranosyl building block 5 was obtained. The anomeric stereocontrol in the glycosylation step with 1,2-O-cyclohexylidene-sn-glycerol (4) was based on anchimeric assistance, thus finally leading to the unprotected core glycolipid 16. Regioselective protection and deprotection procedures permitted the defined attachment of the pentameric glycerophosphate 3 to the 6-hydroxy group of the galactose residue. Introduction of four D-alanyl residues led after global deprotection and purification to target molecule 1a possessing on average about two D-alanyl residues at 2-O of the pentameric glycerophosphate backbone, thus being in close accordance with the structure of the natural material. (C) 2010 Published by Elsevier Ltd.