2,3,4-tri-O-acetyl-1-thio-β-D-xylopyranose | 2595-42-8

• 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: 2,3,4-tri-O-acetyl-1-thio-β-D-xylopyranose
• 英文别名: [(3R,4S,5R,6S)-4,5-diacetyloxy-6-sulfanyloxan-3-yl] acetate
• CAS: 2595-42-8
• 化学式: C₁₁H₁₆O₇S
• 分子量: 292.31
• InChiKey: XACUQSZBPMZEPE-YTWAJWBKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  89.1
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2,3,4-tri-O-acetyl-1-thio-β-D-xylopyranose 在 sodium hydride 、 溶剂黄146 、 1,7-偶氮-15-冠-5 作用下， 反应 3.0h， 生成 1,2-O-isopropylidene-3-S-(2,3,4-tri-O-acetyl-β-D-xylopyranosyl)-3-thio-α-D-glucofuranose
  参考文献：
  名称：

  Positional isomers of thioxylobiose, their synthesis and inducing ability for d-xylan-degrading enzymes in the yeast cryptococcus albidus

  摘要：

  Isomeric S-linked 2-thioxylobiose 10, 3-thioxylobiose 17, and 4-thioxylobiose 19 were conveniently prepared by SN2 displacement of suitable triflylglycoses with the sodium salt of 2,3,4-tri-O-acetyl-1-thio-beta-D-glucopyranose, either in N,N-dimethylformamide, or in oxolan in the presence of a sodium complexing agent. Allyl 3,5-O-isopropylidene-2-O-trifluoromethanesulfonyl-beta-D-lyxofuranoside was a convenient electrophilic precursor for 10, which was smoothly obtained after a short sequence of deprotection involving conversion to the 1-propenyl glycoside. 1,2:5,6-Di-O-isopropylidene-3-O-trifluoromethylsulfonyl-alpha-D-allofuranose and 1,2,3-tri-O-benzoyl-4-O-trifluoromethylsulfonyl-beta-L-arabinopyranose were the respective precursors for 17 and 19. 4-Thioxylobiose has a highly stimulatory effect on the synthesis of enzymes of the xylanolytic system in the yeast Cryptococcus albidus when applied to the cells in the presence of the natural disaccharide inducer (1 --> 4)-beta-D-xylobiose.

  DOI：

  10.1016/s0008-6215(00)90548-2
• 作为产物：
  描述：

  D-吡喃木糖 在 吡啶 、 4-二甲氨基吡啶 、 L-1,4-二硫代苏糖醇 、 氢溴酸 、 碳酸氢钠 、 溶剂黄146 、 potassium thioacetate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 20.5h， 生成 2,3,4-tri-O-acetyl-1-thio-β-D-xylopyranose
  参考文献：
  名称：

  一种潜在的毛发生长刺激剂香花苷的全合成：一种通过一锅 S- 和 O-糖苷键形成的简便合成方法

  摘要：

  首次全合成花斑苷 ( 1 )，对人毛囊真皮乳头细胞表现出强大的增殖活性，从邻氨基苯甲酸开始，经过七个步骤实现了克级总产率 43% ( 11 )。该合成策略采用一锅法，涉及通过亲核取代反应和烯醇-葡萄糖基化形成硫代葡萄糖苷键，以构建1的S- , O-双锁链苷结构。此外，一锅反应对d-葡萄糖以外的几种糖供体表现出广泛的底物适应性，从而以约 84% 的产率提供S , O-双糖苷中间体。

  DOI：

  10.1021/acs.jnatprod.3c00815

文献信息

• Practical synthesis of latent disarmed S-2-(2-propylthio)benzyl glycosides for interrupted Pummerer reaction mediated glycosylation
  作者：Yang Xu、Qian Zhang、Ying Xiao、Pinru Wu、Wei Chen、Zejin Song、Xiong Xiao、Lingkui Meng、Jing Zeng、Qian Wan

  DOI：10.1016/j.tetlet.2017.05.014

  日期：2017.6

  Practical synthetic methods to latent disarmed S-2-(2-propylthio)benzyl (SPTB) glycosides for interrupted Pummerer reaction mediated glycosylation have been discovered. Among them, both coupling reaction of PTB-Cl with glycosyl thiols and BF3·OEt2 promoted reaction of peracylated glycosides with PTB-SH produced peracylated SPTB glycosides in large scales and with high efficiency.

  已经发现了潜在的解除武装的S -2-（2-丙硫基）苄基（SPTB）糖苷用于中断的Pummerer反应介导的糖基化的实用合成方法。其中，PTB-Cl与糖基硫醇的偶联反应和BF 3 ·OEt 2均促进了过酰化的糖苷与PTB-SH的反应，从而大规模，高效地生产了过酰化的SPTB糖苷。
• Syntheses of 1-thio-D-xylose andD-ribose esters of diorganoarsinous acids and their anticancer activity
  作者：Mingzhang Gao、Yiwen Chen、Songde Tan、Joseph H. Reibenspies、Ralph A. Zingaro

  DOI：10.1002/hc.20388

  日期：2008.3

  Several thio-D-xylose and D-ribose esters of dialkylarsinous acids have been synthesized. The crystal structure of 1-S-dimethylarsino-β-D-xylopyranose, 7a, has been obtained. Growth inhibition studies of about 60 strains of human cancer cells have been obtained in vitro for compounds 6a, 7a, 13, and 14. The results reveal that these compounds display a strong inhibition to subpanels of leukemia cells

  已经合成了几种二烷基胂酸的硫代-D-木糖和D-核糖酯。已获得1-S-二甲基胂-β-D-吡喃木糖的晶体结构7a。对化合物6a、7a、13和14进行了约60株人癌细胞的体外生长抑制研究。结果表明，这些化合物在体外对白血病细胞亚群有很强的抑制作用，对抑制白血病细胞具有高选择性。癌细胞的生长。© 2008 Wiley Periodicals, Inc. 杂原子化学 19:199–206, 2008; 在线发表于 Wiley InterScience (www.interscience.wiley.com)。DOI 10.1002/hc.20388
• Synthesis and studies of acetylthioglycoside conjugates of 4-chloro-1,2-dithiole-3-thione as potential antitumor agents
  作者：S. N. Fedorov、A. S. Kuzmich、Yu. E. Sabutskii、A. G. Guzii、R. S. Popov、V. A. Ogurtsov、O. A. Rakitin、S. G. Polonik

  DOI：10.1007/s11172-021-3127-1

  日期：2021.3

  THP-1 human leukemia cells in soft agar, as well as to inhibit the AP-1-dependent transcriptional activity in JB6 Cl41 luc-AP-1 cells, which suggests the possibility of using the new compounds as potential cancer preventive drugs.

  在4,5-二氯-1,2-二硫-3-硫酮与per-氯原子的亲核取代ö的乙酰基-1- mercaptho衍生物d葡萄糖，ð半乳糖，d甘露糖，d木糖，升-阿拉伯糖和d-麦芽糖产生了六种新的4-氯-1,2-二硫代-3-硫酮乙酰硫代糖苷共轭物。这些硫糖苷对软琼脂中的JB6 Cl41 P +小鼠表皮细胞和THP-1人白血病细胞模型具有抗癌活性，并抑制JB6 Cl41 luc-AP中AP-1依赖性转录活性。 -1细胞，这表明使用新化合物作为潜在的癌症预防药物的可能性。
• Catalytic Glycosylation with Glycosyl Thioimidate Donors
  作者：Cristina Lucas-Lopez、Niamh Murphy、Xiangming Zhu

  DOI：10.1002/ejoc.200800503

  日期：2008.9

  of glycosyl thioimidates, glycosyl N-phenyl-trifluorothioacetimidates, were prepared from the readily available glycosyl thiols in excellent yields. These imidates exhibited very good donor properties under the action of catalytic amounts of BF3·Et2O, and the corresponding glycosidation products were formed in very good to excellent yields. Thus, the first catalytic glycosylations with glycosyl thioimidate

  一类新的糖基硫代亚氨酸盐，即糖基 N-苯基-三氟硫代乙亚胺酸盐，是从容易获得的糖基硫醇以优异的产率制备的。这些亚胺酯在催化量的BF3·Et2O的作用下表现出非常好的供体性质，并且相应的糖苷化产物以非常好的收率形成。因此，实现了与糖基硫代亚氨酸酯供体的第一次催化糖基化。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)
• Thio-click reaction of 2-deoxy-<i>exo</i>-glycals towards new glycomimetics: stereoselective synthesis of <i>C</i>-2-deoxy-<scp>d</scp>-glycopyranosyl compounds
  作者：János József、László Juhász、László Somsák

  DOI：10.1039/c8nj06138f

  日期：——

  conditions. Photoinitiated thiol–ene additions of these exo-glycals resulted in the corresponding C-(2-deoxy-D-glycopyranosyl)methyl sulfides in medium to good yields with exclusive regio- and stereoselectivities in most cases. Several disaccharide mimics with a C–S moiety in place of the glycosidic oxygen were also obtained.

  一系列的2-脱氧吡喃葡萄糖基氰化物与d -阿拉伯糖，d -来苏，d -赤，和d -苏式构型，由相应的烯糖合成通过2-脱氧吡喃葡萄糖基乙酸盐。通过在甲苯磺酰肼存在下用NaH 2 PO 2 / Ra-Ni还原将氰化物转化为脱水醛糖甲苯磺酰hydr。在改良的Bamford–Stevens条件下，甲苯磺酰azo提供了2-deoxy- exo - glycals。这些外糖的光引发硫醇烯加成反应产生了相应的在大多数情况下，C-（2-脱氧-D-甘露糖基糖基）甲基硫化物具有中等至良好的收率，并且具有独特的区域选择性和立体选择性。还获得了几个具有C–S部分代替糖苷氧的二糖模拟物。