thiophenyl 2-deoxy-3,4,6-tri-O-acetyl-D-glucopyranoside | 151767-37-2

• 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: thiophenyl 2-deoxy-3,4,6-tri-O-acetyl-D-glucopyranoside
• 英文别名: D-arabino-Hexopyranoside, phenyl 2-deoxy-1-thio-, 3,4,6-triacetate；[(2R,3S,4R)-3,4-diacetyloxy-6-phenylsulfanyloxan-2-yl]methyl acetate
• CAS: 151767-37-2
• 化学式: C₁₈H₂₂O₇S
• 分子量: 382.434
• InChiKey: DMRACQUKAOGJQX-KQWXFDBXSA-N

物化性质

• 沸点：
  486.1±45.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  26
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  113
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  thiophenyl 2-deoxy-3,4,6-tri-O-acetyl-D-glucopyranoside 在 咪唑 、 molecular sieve 、 sodium methylate 、 sodium acetate 、 碳酸氢钠 、 lithium dihydronaphthylide radical 、 间氯过氧苯甲酸 、 pyridinium chlorochromate 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 52.05h， 生成 [(2S,4R,5R,6R)-4,5-Bis-(tert-butyl-dimethyl-silanyloxy)-6-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-pyran-2-yl]-phenyl-methanone
  参考文献：
  名称：

  2-脱氧-D-吡喃葡萄糖基苯基砜的制备和还原锂化：对C-糖苷的高度立体选择性

  摘要：

  2-脱氧-D-吡喃葡萄糖基苯基砜3a-c已从商品三-O-乙酰基-D-葡萄糖1合成，产率为75-83％。它们通过萘二甲酸锂的还原性脱磺酰基作用以及中间体糖基锂5与醛的反应导致具有高立体选择性的α-DC-吡喃葡萄糖苷。

  DOI：

  10.1016/s0040-4039(00)95048-2
• 作为产物：
  描述：

  乙酰化葡萄烯糖 在 盐酸 、 N,N-二异丙基乙胺 作用下， 以 甲苯 为溶剂， 反应 3.0h， 生成 thiophenyl 2-deoxy-3,4,6-tri-O-acetyl-D-glucopyranoside
  参考文献：
  名称：

  2-脱氧-D-吡喃葡萄糖基苯基砜的制备和还原锂化：对C-糖苷的高度立体选择性

  摘要：

  2-脱氧-D-吡喃葡萄糖基苯基砜3a-c已从商品三-O-乙酰基-D-葡萄糖1合成，产率为75-83％。它们通过萘二甲酸锂的还原性脱磺酰基作用以及中间体糖基锂5与醛的反应导致具有高立体选择性的α-DC-吡喃葡萄糖苷。

  DOI：

  10.1016/s0040-4039(00)95048-2

文献信息

• 一类蒽醌并三氮唑抗生素核苷类似物、合成方 法及其在制备抗肿瘤或抗病毒药物中的应用
  申请人：河南师范大学

  公开号：CN108822171B

  公开（公告）日：2021-07-13

  本发明公开了一类蒽醌并三氮唑抗生素核苷类似物，合成方法及其在制备抗肿瘤或抗病毒药物中的应用，属于化学及医药技术领域。本发明的技术方案要点为：一类蒽醌并三氮唑抗生素核苷类似物，其结构式为本发明还具体公开了该蒽醌并三氮唑抗生素核苷类似物的合成方法及其在制备抗肿瘤或/和抗病毒药物中的应用。本发明制得了一系列结构新颖且具有生物活性的蒽醌并三氮唑抗生素核苷类似物，通过生物活性测试发现该类化合物具有良好的抗肿瘤及抗病毒活性，能够用于制备抗肿瘤或抗病毒药物，进而有效克服目前长期使用蒽环抗生素类药物所产生的心脏毒性及抗药性等毒副作用。
• Recent advances in the synthesis of 2-deoxy-glycosides
  作者：Dianjie Hou、Todd L. Lowary

  DOI：10.1016/j.carres.2009.07.013

  日期：2009.10

  Glycosides of 2-deoxy-sugars, monosaccharides in which the hydroxyl group at C-2 is replaced with a hydrogen atom, occur widely in natural products and therefore have been the subject of intense synthetic activity. The report summarizes recent advances in this area, with a particular focus on work published since an earlier review on the topic, in 2000 (Marzabadi, C. H.: Franck, R. W. Tetrahedron 2000, 56, 8385-8417). (C) 2009 Elsevier Ltd. All rights reserved.
• Solid-Phase-Assisted Solution-Phase Synthesis with Minimum Purification—Preparation of2-Deoxyglycoconjugates from Thioglycosides
  作者：Janis Jaunzems、Edgar Hofer、Martin Jesberger、Georgia Sourkouni-Argirusi、Andreas Kirschning

  DOI：10.1002/anie.200390307

  日期：2003.3.10
• Syntheses and Biological Activities of Disaccharide Daunorubicins
  作者：Guisheng Zhang、Lanyan Fang、Lizhi Zhu、Josephine E. Aimiuwu、Jie Shen、Hao Cheng、Mark T. Muller、Gun Eui Lee、Duxin Sun、Peng George Wang

  DOI：10.1021/jm050144u

  日期：2005.8.1

  Carbohydrate moiety is found in many anticancer nature products. To explore the carbohydrate moiety of daunorubicin in enhancing anticancer efficacy, several daunorubicin derivatives bearing disaccharide (1-8) have been synthesized. Their cytotoxicities were tested in leukemia K562 and colon cancer SW620 cells. Topoisomerase II (topo II) poisoning was performed with the in vivo complex of topoisomerase bioassay. In both cell lines, compounds with various terminal 2,6-dideoxy sugars (compounds 1, 3, 5, and 8) showed 30- to 60-fold higher anticancer activity than compounds with 2-deoxy- or 6-deoxy sugar (compounds 6 and 7). Compounds with an alpha-linkage between two sugar units (compound 3) showed 35-fold higher anticancer activity than compounds with a beta-linkage (compound 4). In addition, the anticancer activities of these compounds correlated with their ability to target topo II mediated genomic DNA damage in vivo. Compounds 1 and 3 with 2,6-dideoxy sugars produced more covalent topo-DNA complex than compounds with 2-deoxy sugar (6) and 6-deoxy sugar (7). Compounds with an alpha-configuration of terminal 2,6-dideoxy sugar (compounds 1 and 3) showed higher topo II poisoning than their counterparts with the beta-configuration (compounds 2 and 4). These results indicate that sugar moieties in daunorubicin play a significant role in its anticancer activity and topo II inhibition. The second sugar of disaccharide daunorubicin should possess 2,6-dideoxy with alpha-linkage to the first sugar to exhibit better anticancer activity.
• Anomeric activation of thioglycosides and preparation of deoxyglycosides using polymer-bound iodate(I) complexes
  作者：Janis Jaunzems、Georgia Sourkouni-Argirusi、Martin Jesberger、Andreas Kirschning

  DOI：10.1016/s0040-4039(02)02708-9

  日期：2003.1

  New thiophilic polymer-bound haloate(l) complexes are presented which are well suited for the polymer-assisted solution-phase activation of 2-deoxythioglycosides. In the presence of alcohols 2-deoxyglycosides are obtained in yields between 60 and 95%. Isolation of the target glycosides is further simplified by removing the byproduct diphenyldisulfide by reductive work-up. Here also a polymer-bound reagent, namely borohydride exchange resin, served as a tool for sequestering the sulfur-containing impurities. (C) 2003 Elsevier Science Ltd. All rights reserved.