3-S-acetyl-1,2:5,6-di-O-isopropylidene-3-thio-α-D-glucose | 28251-80-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-S-acetyl-1,2:5,6-di-O-isopropylidene-3-thio-α-D-glucose
• 英文别名: diacetone-3-deoxy-Ac-S-Glc；3-S-acetyl-1,2;5,6-di-O-isopropylidene-α-D-gluco-furanose；3-S-acetyl-1,2:5,6-di-O-isopropylidene-3-deoxy-3-thio-α-D-glucofuranose；S-[(3aR,5R,6S,6aS)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-yl] ethanethioate
• CAS: 28251-80-1
• 化学式: C₁₄H₂₂O₆S
• 分子量: 318.391
• InChiKey: ZBBVHGNVUXSQAK-PZWNZHSQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  88.5
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3-S-acetyl-1,2:5,6-di-O-isopropylidene-3-thio-α-D-glucose 在 sodium butanolate 作用下， 以 正丁醇 为溶剂， 以70%的产率得到3,6-anhydro-1,2-O-isopropylidene-3-thio-α-D-glucofuranose
  参考文献：
  名称：

  Synthesis of novel 3′,6′-dideoxy-3′,6′-epithio and 2′,6′-dideoxy-2′,6′-epithio nucleosides

  摘要：

  New 3',6'-dideoxy-3',6'-epithio and 2',6'-dideoxy-2',6'-epithionucleosides were prepared from 3',6'-dideoxy-3',6'-epithioglucofuranose derivatives, which were obtained from 3-trifluoromethanesulfonyl diacetone allose. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)00721-7
• 作为产物：
  描述：

  1,2:5,6-di-O-isopropylidene-3-O-trifluoromethanesulfonyl-α-D-allofuranose 在 吡啶 、 lithium aluminium tetrahydride 作用下， 以 乙醚 、 乙腈 为溶剂， 反应 21.0h， 生成 3-S-acetyl-1,2:5,6-di-O-isopropylidene-3-thio-α-D-glucose
  参考文献：
  名称：

  The thiocyanate route to derivatives of 3-thio-d-glucose and 3-thio-d-allose

  摘要：

  DOI：

  10.1016/s0008-6215(00)85600-1

文献信息

• Synthesis, photophysical properties, and photodynamic activity of positional isomers of TFPP-glucose conjugates
  作者：Arif Fadlan、Hiroki Tanimoto、Tatsuya Ito、Yusuke Aritomi、Maho Ueno、Masaya Tokuda、Shiho Hirohara、Makoto Obata、Tsumoru Morimoto、Kiyomi Kakiuchi

  DOI：10.1016/j.bmc.2018.02.031

  日期：2018.5

  The synthesis and characterization of a ‘complete set’ of positional isomers of tetrakis(perfluorophenyl)porphyrins (TFPP)-glucose conjugates (1OH, 2OH, 3OH, 4OH, and 6OH) are reported herein. The cellular uptake and photocytotoxicity of these conjugates were examined in order to investigate the influence of location of the TFPP moiety on the d-glucose molecule on the biological activity of the conjugates

  本文报道了四（全氟苯基）卟啉（TFPP）-葡萄糖缀合物（1OH，2OH，3OH，4OH和6OH）的位置异构体的“完整集”的合成和表征。为了研究TFPP部分在d-葡萄糖分子上的位置对缀合物的生物学活性的影响，检查了这些缀合物的细胞摄取和光细胞毒性。一种在体外生物评价，结果这些特定的异构体对细胞摄取和细胞毒性比别人更大的影响。TFPP-葡萄糖结合物1OH，3OH和与2OH和6OH取代的异构体相比，发现4OH在几种类型的癌细胞中具有优异的光细胞毒性。
• New Oligosaccharide Analogues: Non-Glycosidically Linked Thioether-­Bridged Pseudodisaccharides
  作者：Ian Cumpstey

  DOI：10.1055/s-2006-947338

  日期：2006.7

  The synthesis of six disaccharide analogues is reported. The pseudodisaccharides each consist of two monosaccharide residues linked non-glycosidically via a thioether functionality; both C 2 -symmetric and unsymmetrically substituted examples are described. The synthesis was achieved by first introducing an acetate-protected sulfur into partially protected carbohydrates by S N 2 displacement of sulfonate

  报道了六种二糖类似物的合成。每个假双糖由两个单糖残基组成，通过硫醚官能团非糖苷连接；描述了C 2 对称和不对称取代的实例。该合成是通过首先通过硫代乙酸酯取代磺酸酯的 SN 2 将乙酸酯保护的硫引入部分保护的碳水化合物中来实现的。硫的脱乙酰之后用另一种碳水化合物磺酸盐衍生物处理，第二次 SN 2 置换得到假双糖产物。
• From glycoside hydrolases to thioglycoligases: the synthesis of thioglycosides
  作者：Robert V. Stick、Keith A. Stubbs

  DOI：10.1016/j.tetasy.2004.12.004

  日期：2005.1

  any thioglycosides––only the products of O-glycosylation were formed. However, thioglycosides were formed when a thioglycoligase was used to mediate the reaction between acceptor and donor. In fact, pyranose acceptors possessing a thiol group at C3, C4 or C6 (but not C2) were all capable of conversion into thioglycosides. Some comment is given regarding the mechanism of the various processes.

  用适当的糖基供体和糖苷水解酶或糖合酶处理各种含活性硫醇基的糖基受体，都不能产生任何硫糖苷，只能形成O-糖基化产物。然而，当使用硫代糖基寡糖酶来介导受体和供体之间的反应时，形成了硫代糖苷。实际上，在C3，C4或C6具有巯基的吡喃糖受体（但没有C2）均能够转化为硫糖苷。给出了有关各种过程机制的一些评论。
• Synthesis of sulfur-linked analogues of nigerose, laminarabiose, laminaratriose, gentiobiose, gentiotriose, and laminaran trisaccharide Y
  作者：Marie-Odile Contour-Galcera、Jean-Michel Guillot、Carmen Ortiz-Mellet、Françoise Pflieger-Carrara、Jacques Defaye、Jacques Gelas

  DOI：10.1016/0008-6215(95)00339-8

  日期：1996.2

  Sulfur-linked analogues of 3-O-alpha-D-glucopyranosyl-D-glucose (nigerose), 3-O-beta-D-glucopyranosyl-D-glucose (laminarabiose), 6-O-beta-D-glucopyranosyl-D-glucose (gentiobiose), O-beta-D-glucopyranosyl-(1-->3)-O-beta-D-glucopyranosyl-(1-->3)-D-glucos e (laminaratriose), O-beta-D-glucopyranosyl)-(1-->6)-O-beta-D-glucopyranosyl-(1-->6)-D-gluco se (gentiotriose) and 3,6-di-O-beta-D-glucopyranosyl-D-glucose

  N-二甲基甲酰胺（用于6和21）或在四氢呋喃中在冠醚存在下（用于11）。涉及非异构硫醇盐与2,3,4,6-四-O-乙酰基-α-D-吡喃葡萄糖基溴化物反应的序列可替代地用于制备11和21，但事实证明不太令人满意。硫代三糖16、29和37的制备涉及混合方法。
• Non-Glycosidically Linked Pseudodisaccharides: Thioethers, Sulfoxides, Sulfones, Ethers, Selenoethers, and Their Binding to Lectins
  作者：Ian Cumpstey、Clinton Ramstadius、Tashfeen Akhtar、Irwin J. Goldstein、Harry C. Winter

  DOI：10.1002/ejoc.200901481

  日期：2010.4

  Hydrolytically stable non-glycosidically linked tail-to-tail pseudodisaccharides are linked by a single bridging atom remote from the anomeric centre of the constituent monosaccharides. Some such pseudodisaccharides with sulfur or oxygen bridges were found to act as disaccharide mimetics in their binding to the Banana Lectin and to Concanavalin A. A versatile synthetic route to a small library of such

  水解稳定的非糖苷连接的尾对尾假二糖通过远离组成单糖的异头中心的单个桥原子连接。发现一些具有硫桥或氧桥的此类假二糖在与香蕉凝集素和刀豆球蛋白 A 结合时充当二糖模拟物。描述了一种合成此类化合物的小型文库的通用途径。