phenylmethyl 3-O-acetyl-2,6-dideoxy-4-O-[(2R,6R)-5,6-dihydro-6-methyl-5-oxo-2H-pyran-2-yl]-β-D-ribo-hexopyranoside | 934021-77-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenylmethyl 3-O-acetyl-2,6-dideoxy-4-O-[(2R,6R)-5,6-dihydro-6-methyl-5-oxo-2H-pyran-2-yl]-β-D-ribo-hexopyranoside
• 英文别名: [(2R,3R,4S,6R)-2-methyl-3-[[(2R,6R)-6-methyl-5-oxo-2H-pyran-2-yl]oxy]-6-phenylmethoxyoxan-4-yl] acetate
• CAS: 934021-77-9
• 化学式: C₂₁H₂₆O₇
• 分子量: 390.433
• InChiKey: ACGXQFAPNMASSQ-GCIOHYTISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  80.3
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  phenylmethyl 3-O-acetyl-2,6-dideoxy-4-O-[(2R,6R)-5,6-dihydro-6-methyl-5-oxo-2H-pyran-2-yl]-β-D-ribo-hexopyranoside 在 sodium tetrahydroborate 、 cerium(III) chloride 作用下， 以92%的产率得到phenylmethyl 3-O-acetyl-2,6-dideoxy-4-O-[(2R,6R)-5,6-dihydro-5-hydroxy-6-methyl-2H-pyran-2-yl]-β-D-ribo-hexopyranoside
  参考文献：
  名称：

  Recent advances in the synthesis of 2-deoxy-glycosides

  摘要：

  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.

  DOI：

  10.1016/j.carres.2009.07.013
• 作为产物：
  描述：

  (2R)-2-tert-butyldimethylsilanyloxymethyl-6-hydroxy-6H-pyran-3-one 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex sodium acetate 、 三苯基膦 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 4.0h， 生成 phenylmethyl 3-O-acetyl-2,6-dideoxy-4-O-[(2R,6R)-5,6-dihydro-6-methyl-5-oxo-2H-pyran-2-yl]-β-D-ribo-hexopyranoside
  参考文献：
  名称：

  从头开始的2-Deoxy-β-糖苷方法：地高糖和Digitoxin 1的不对称合成

  摘要：

  已经开发出了高度对映选择性和直接的途径来制备三糖天然产物地高糖和洋地黄毒苷。该方法的关键是钯催化糖基化反应，还原性1,3-移位，非对映选择性二羟基化和区域选择性保护的迭代应用。天然产物digoxose的第一全合成是在非手性从2- acylfuran 19个总步骤完成，和洋地黄毒苷在15个步骤塑成从洋地黄毒苷开始2和吡喃酮8 β。这种灵活的合成策略还允许制备地高糖和洋地黄毒苷的单糖和二糖类似物。

  DOI：

  10.1021/jo062534+

文献信息

• A Direct Comparison of the Anticancer Activities of Digitoxin MeON-Neoglycosides and <i>O</i>-Glycosides
  作者：Anand Krishnan V. Iyer、Maoquan Zhou、Neelam Azad、Hosam Elbaz、Leo Wang、Derek K. Rogalsky、Yon Rojanasakul、George A. O'Doherty、Joseph M. Langenhan

  DOI：10.1021/ml1000933

  日期：2010.10.14

  Digitoxin is a cardiac glycoside currently being investigated for potential use in oncology; however, an investigation of anticancer activity as a function, of oligosaccharide chain length has not yet been performed. We generated mono-, di-, and tri-O-digitoxoside derivatives, of digitoxin and compared their activities to the corresponding MeON-neoglycosides. Both classes of cardenolide derivatives display comparable oligosaccharide chain length-dependent cytotoxicity toward human cancer cell lines. Further investigation revealed that both classes of compounds induce caspase-9-mediated apoptosis in non-small cell lung cancer cells (NCI-H460). Because O-glycosides and MeON-neoglycosides share a similar mode of action, the convenience of MeON-neoglycosylation could be exploited in future SAR work to rapidly survey large numbers of carbohydrates to prioritize selected O-glycoside candidates for traditional synthesis.