phenyl 2,3-di-O-benzoyl-1-thio-α-D-arabinofuranoside | 869216-48-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl 2,3-di-O-benzoyl-1-thio-α-D-arabinofuranoside
• 英文别名: [(2R,3R,4S,5R)-4-benzoyloxy-2-(hydroxymethyl)-5-phenylsulfanyloxolan-3-yl] benzoate
• CAS: 869216-48-8
• 化学式: C₂₅H₂₂O₆S
• 分子量: 450.512
• InChiKey: GRIFKAMIZPJKKO-ILSIFQBBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  32
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  107
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  phenyl 2,3-di-O-benzoyl-1-thio-α-D-arabinofuranoside 在 吡啶 、 2,4,6-三甲基吡啶 、 N-碘代丁二酰亚胺 、 三乙基硅基三氟甲磺酸酯 、 silver trifluoromethanesulfonate 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 9.17h， 生成 4-(2-chloroethoxy)phenyl 5-O-(2,3-di-O-benzoyl-α-D-arabinofuranosyl)-2,3-di-O-benzoyl-α-D-arabinofuranoside
  参考文献：
  名称：

  阿拉伯呋喃糖1,2,5-原苯甲酸酯作为线性α（1→5）连接的低聚阿拉伯呋喃糖苷的单一前体

  摘要：

  使用在非还原端具有未保护的伯羟基的选择性保护的单糖，二糖和三糖硫代糖苷结构单元，仅可从3-O-苯甲酰基β-d-阿拉伯呋喃糖1,2,5-原苯甲酸酯中一步获得。合成线性α（1→5）连接的低聚阿拉伯呋喃糖苷直至八糖。所获得的寡糖包含4-（2-氯乙氧基）苯基（CEP）或4-（2-叠氮基乙氧基）苯基（AEP）预间隔子糖苷配基，其允许制备新糖缀合物。

  DOI：

  10.1016/j.carres.2017.11.002
• 作为产物：
  描述：

  在 甲醇 、 乙酰氯 作用下， 反应 14.0h， 以94%的产率得到phenyl 2,3-di-O-benzoyl-1-thio-α-D-arabinofuranoside
  参考文献：
  名称：

  An Efficient Synthesis of a Dimer of the Tetrasaccharide Present in Motif B of theMycobacterium tuberculosisCell Wall

  摘要：

  利用2,3,5-三-O-苯甲酰基-α-d-阿洛呋喃糖基三氯乙酰亚胺酯、5-O-乙酰基-2,3-二-O-苯甲酰基-α-d-阿洛呋喃糖基三氯乙酰亚胺酯、1,2-O-异亚丙基-5-O-三苯甲基-β-d-阿洛呋喃糖、十二烷基2,3-二-O-苯甲酰基-α-d-阿洛呋喃糖苷和苯基2,3-二-O-苯甲酰基-1-硫-α-d-阿洛呋喃糖苷作为合成子，开发出一种高效合成3,5-分支的八阿洛糖苷的方法，该化合物是存在于结核分枝杆菌细胞壁基序B中的四糖二聚体。

  DOI：

  10.1055/s-2005-872674

文献信息

• Regioselective Glycosylation Method Using Partially Protected Arabino- and Galactofuranosyl Thioglycosides as Key Glycosylating Substrates and Its Application to One-Pot Synthesis of Oligofuranoses
  作者：Li-Min Deng、Xia Liu、Xing-Yong Liang、Jin-Song Yang

  DOI：10.1021/jo300084g

  日期：2012.4.6

  development of a novel regioselective furanosylation methodology using partially protected furanosyl thioglycosides as central glycosylating building blocks and its application in the efficient one-pot synthesis of a series of linear and branched-type arabino- and galactofuranoside fragments structurally related to the cell wall polysaccharides of Mycobacterium tuberculosis, Streptococcus pneumoniae serostype

  我们在本文中描述了使用部分保护的呋喃糖基硫糖苷作为中心糖基化结构单元的新型区域选择性呋喃糖基化方法的开发及其在一系列结构上与之相关的线性和支链型阿拉伯糖和半乳糖呋喃糖苷片段的有效一锅合成中的应用结核分枝杆菌，肺炎链球菌血清型35A和甜菜的细胞壁多糖。
• Efficient one-pot syntheses of α-d-arabinofuranosyl tri- and tetrasaccharides present in cell wall polysaccharide of Mycobacterium tuberculosis
  作者：Xing-Yong Liang、Li-Min Deng、Xia Liu、Jin-Song Yang

  DOI：10.1016/j.tet.2009.11.038

  日期：2010.1

  Two alpha-D-arabinofuramosyl oligosaccharides (2 and 3) found as constituent parts of the polysaccharide portion from the cell wall of Mycobacterium tuberculosis have been efficiently synthesized via a one-pot glycosylation procedure in which a key step is the chemoselective activation between D-arabinofuranosyl trichloroacetimidate donor 4 and partially protected aryl thioglycosides 5 or 7, respectively. (C) 2009 Elsevier Ltd. All rights reserved.
• Ring opening of acylated β-d-arabinofuranose 1,2,5-orthobenzoates with nucleophiles allows access to novel selectively-protected arabinofuranose building blocks
  作者：Nikita M. Podvalnyy、Sergey L. Sedinkin、Polina I. Abronina、Alexander I. Zinin、Ksenia G. Fedina、Vladimir I. Torgov、Leonid O. Kononov

  DOI：10.1016/j.carres.2010.11.002

  日期：2011.1

  beta-D-Arabinofuranose 1,2,5-orthobenzoates with 3-O-acetyl, 3-O-benzoyl, and 3-O-chloroacetyl groups were prepared in an efficient manner starting from readily available crystalline methyl 2,3,5-tri-O-benzoyl-alpha-D-arabinofuranoside, and ring-opening reactions of these compounds with O- and S-nucleophiles were studied. Optimized conditions leading to the formation of the respective monosaccharide adducts (up to 96% isolated yields) and to alpha-(1 -> 5)-linked disaccharide thioglycosides with 5'-OH unprotected (up to 30% isolated yields) were found. Basing on these results, a novel approach for effective differentiation of 3,5-diol system and 2-hydroxy group in arabinofuranose thioglycosides was proposed. The selectively protected derivatives prepared are valuable building blocks for the assembly of linear and branched oligoarabinofuranosides. (C) 2010 Elsevier Ltd. All rights reserved.
• Tuning Effect of Silyl Protecting Groups on the Glycosylation Reactivity of Arabinofuranosyl Thioglycosides
  作者：Xing-Yong Liang、Hua-Chao Bin、Jin-Song Yang

  DOI：10.1021/ol401166x

  日期：2013.6.7

  The tuning effect of silyl protecting groups on the glycosylation reactivity of arabinofuranosyl phenyl thioglycoside donors Is presented. Silyl ethers on the 3-, 5-, and 3,5-positions of the arabinofuranose ring are found to have an arming effect on the donor reactivity, whereas the cyclic 3,5-acetal type protecting groups reduce the reactivity.
• An Efficient Synthesis of a Dimer of the Tetrasaccharide Present in Motif B of the<i>Mycobacterium tuberculosis</i>Cell Wall
  作者：Jun Ning、Xiangdong Mei

  DOI：10.1055/s-2005-872674

  日期：——

  An efficient method for the synthesis of 3,5-branched ­octaarabinoside, which is a dimer of the tetrasaccharide present in motif B of the Mycobacterium tuberculosis cell wall, has been ­developed by using 2,3,5-tri-O-benzoyl-α-d-arabinofuranosyl trichloroacetimidate, 5-O-acetyl-2,3-di-O-benzoyl-α-d-arabinofuranosyl trichloroacetimidate, 1,2-O-isopropylidene-5-O-trityl-β-d-arabinofuranose, dodecyl 2,3-di-O- benzoyl-α-d-arabinofuranoside and phenyl 2,3-di-O-benzoyl-1-thio-α-d-arabinofuranoside as synthons.

  利用2,3,5-三-O-苯甲酰基-α-d-阿洛呋喃糖基三氯乙酰亚胺酯、5-O-乙酰基-2,3-二-O-苯甲酰基-α-d-阿洛呋喃糖基三氯乙酰亚胺酯、1,2-O-异亚丙基-5-O-三苯甲基-β-d-阿洛呋喃糖、十二烷基2,3-二-O-苯甲酰基-α-d-阿洛呋喃糖苷和苯基2,3-二-O-苯甲酰基-1-硫-α-d-阿洛呋喃糖苷作为合成子，开发出一种高效合成3,5-分支的八阿洛糖苷的方法，该化合物是存在于结核分枝杆菌细胞壁基序B中的四糖二聚体。