S-phenyl 3,4,6-tri-O-acetyl-2-deoxy-β-D-arabino-thiohexopyranoside | 135700-54-8

• 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: S-phenyl 3,4,6-tri-O-acetyl-2-deoxy-β-D-arabino-thiohexopyranoside
• 英文别名: thiophenyl 2-deoxy-3,4,6-tri-O-acetyl-β-D-glucopyranoside；S-phenyl 3,4,6-tri-O-acetyl-2-deoxy-1-thio-β-D-glucopyranoside；[(2R,3S,4R,6S)-3,4-diacetyloxy-6-phenylsulfanyloxan-2-yl]methyl acetate
• CAS: 135700-54-8
• 化学式: C₁₈H₂₂O₇S
• 分子量: 382.434
• InChiKey: DMRACQUKAOGJQX-BDXSIMOUSA-N

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：

  S-phenyl 3,4,6-tri-O-acetyl-2-deoxy-β-D-arabino-thiohexopyranoside 在 sodium 作用下， 以 甲醇 为溶剂， 反应 1.5h， 生成 phenyl 2-deoxy-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  对4,6- O-苄叉基定向β-甘露聚糖基和β-葡糖基烷基化中C2-O2和C3-O3键的影响

  摘要：

  描述了4,6 - O-亚苄基保护的2-deoxyarabino-，3-deoxyarabino-和3-deoxyribothioglycosides的合成及其糖基化反应，并通过1-苯亚磺酰基哌啶/三氟甲磺酸酐或二苯亚砜/三氟甲烷磺酸酐进行活化，研究过。与分别为α-和β-选择性的相应的4，6 - O-亚苄基保护的葡萄糖基和甘露糖基供体相反，在所有情况下均观察到较差的非对映选择性。根据葡糖基和甘露糖基供体中C2-O2和C3-O3键之间的相互作用以及这种相互作用对中间糖基氧杂碳鎓离子形成的难易程度的影响，讨论了这种选择性差的原因。

  DOI：

  10.1021/jo061417b
• 作为产物：
  描述：

  2-Deoxy-D-glucose 在 吡啶 、 三氟化硼乙醚 作用下， 以 甲苯 为溶剂， 反应 26.0h， 生成 S-phenyl 3,4,6-tri-O-acetyl-2-deoxy-β-D-arabino-thiohexopyranoside
  参考文献：
  名称：

  Syntheses and Biological Activities of Disaccharide Daunorubicins

  摘要：

  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.

  DOI：

  10.1021/jm050144u

文献信息

• A concise method for the preparation of glycosyl fluorides via displacement reactions of 1-arylthioglycosides with 4-methyl(difluoroiodo)benzene
  作者：Stephen Caddick、William B. Motherwell、John A. Wilkinson

  DOI：10.1039/c39910000674

  日期：——

  A variety of usefully functionalised 1-fluoroglycosides may be prepared under mild conditions from their corresponding arylthioglycoside derivatives by reaction with 4-methyl(difluoroiodo)benzene.

  通过与 4-甲基（二氟碘）苯反应，可以在温和的条件下从相应的芳基硫代糖苷衍生物中制备出各种有用的官能化 1-氟糖苷。
• Stereoselective <i>O</i> ‐Glycosylations by Pyrylium Salt Organocatalysis**
  作者：Michael Martin Nielsen、Thomas Holmstrøm、Christian Marcus Pedersen

  DOI：10.1002/anie.202115394

  日期：2022.2

  A glycosylation method for non-specialists: Commercially available pyrylium salts catalyze stereoselective glycosylation reactions with trichloroacetimidate electrophiles. A wide range of phenolic nucleophiles are compatible with the procedure. The standard conditions involve mixing three components at ambient conditions and proceed with minimal formation of undesired by-products.

  非专业人士的糖基化方法：市售的吡喃盐催化立体选择性糖基化反应与三氯乙酰亚胺酯亲电子试剂。多种酚类亲核试剂与该程序兼容。标准条件包括在环境条件下混合三种组分，并以最少的不希望的副产物形成进行。
• Total Synthesis of Cytosaminomycin C
  作者：Hideyuki Sugimura、Risa Watanabe

  DOI：10.1246/cl.2008.1038

  日期：2008.10.5

  The first synthesis of cytosaminomycin C has been accomplished by employing intramolecular glycosylation for the β-selective formation of the 2′-deoxyhexopyranosyl nucleoside part as a key reaction.

  细胞胺霉素 C 的首次合成是通过采用分子内糖基化来选择性形成 2'-脱氧吡喃己糖基核苷部分作为关键反应来完成的。
• Preparation of 1-fluoroglycosides from 1-arylthio and 1-arylselenoglycosides using 4-methyl(difluoroiodo)benzene
  作者：S. Caddick、L. Gazzard、W.B. Motherwell、J.A. Wilkinson

  DOI：10.1016/0040-4020(95)00889-g

  日期：1996.1

  Treatment of readily available thio- and selenoglycosides with the reagent 4-methyl(difluoroiodo)benzene leads to the formation of the corresponding fluoroglycosides in moderate to good yield.