6,7-dihydroapodantheroside | 42830-26-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 6,7-dihydroapodantheroside
• 英文别名: adoxoside；Dihydrogeniposid；methyl (1S,4aS,7S,7aS)-7-(hydroxymethyl)-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylate
• CAS: 42830-26-2
• 化学式: C₁₇H₂₆O₁₀
• 分子量: 390.387
• InChiKey: MAHXAEHBKGBEBY-OBFZKGLGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  155
• 氢给体数：
  5
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  6,7-dihydroapodantheroside 在 盐酸 、 4-甲基苯磺酸吡啶 、 三氯化硼 、 sodium hydride 、 臭氧 、 copper(II) sulfate 、 高碘酸 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 丙酮 为溶剂， 反应 69.75h， 生成 [(1S,2S,3R)-3-[(6-aminopurin-9-yl)methyl]-2-(hydroxymethyl)cyclopentyl]methanol
  参考文献：
  名称：

  Stereoselective Hydrogenation and Ozonolysis of Iridoids. Conversion into Carbocyclic Nucleoside Analogues

  摘要：

  Stereoselective hydrogenation of the iridoids geniposide (9) and aucubin (19) was achieved by using the 1-methyl-1-methoxyethyl ether as a protecting group for the allylic alcohol, as it enhanced the stereoselectivity and prevented undesired hydrogenolysis. Ozonolysis of the hydrogenation product from 9, adoxoside (11), with reductive workup, afforded either a chiral lactone (25) or a chiral polyol (26), depending on the reduction conditions. Polyol 26 was subjected to protecting-group manipulation and subsequent oxidation and reductions to yield cyclopentane building blocks (29-34), which, by Mitsunobu couplings with purines, afforded carbocyclic nucleoside analogues (7, 8, and 35).

  DOI：

  10.1021/np990288+
• 作为产物：
  描述：

  京尼平甙 在 palladium on activated charcoal 氢气 、 4-甲基苯磺酸吡啶 、 三乙胺 作用下， 以 乙醇 、 丙酮 为溶剂， 反应 43.5h， 生成 6,7-dihydroapodantheroside
  参考文献：
  名称：

  Stereoselective Hydrogenation and Ozonolysis of Iridoids. Conversion into Carbocyclic Nucleoside Analogues

  摘要：

  Stereoselective hydrogenation of the iridoids geniposide (9) and aucubin (19) was achieved by using the 1-methyl-1-methoxyethyl ether as a protecting group for the allylic alcohol, as it enhanced the stereoselectivity and prevented undesired hydrogenolysis. Ozonolysis of the hydrogenation product from 9, adoxoside (11), with reductive workup, afforded either a chiral lactone (25) or a chiral polyol (26), depending on the reduction conditions. Polyol 26 was subjected to protecting-group manipulation and subsequent oxidation and reductions to yield cyclopentane building blocks (29-34), which, by Mitsunobu couplings with purines, afforded carbocyclic nucleoside analogues (7, 8, and 35).

  DOI：

  10.1021/np990288+

文献信息

• Iridoids from Viburnum betulifolium
  作者：Søren Rosendal Jensen、Bent Juhl Nielsen、Viggo Norn

  DOI：10.1016/s0031-9422(00)80753-0

  日期：——

  Abstract Two iridoid glycosides have been isolated from Viburnum betulifolium . Viburnalloside, the major leaf glycoside, is composed of an iridoid aglucone acylated at C-1 with isovaleric acid and with a di- O -acetyl-β- D -allopyranosyl moiety attached through a glycosidic bond to C-11. Decapetaloside (10-hydroxyiridodial glucoside) has been isolated from the bark. The structure and absolute configuration

  摘要 从桦褐孔菌中分离得到两种环烯醚萜苷。Viburnalloside 是主要的叶糖苷，由在 C-1 处用异戊酸酰化的环烯醚萜苷和通过糖苷键连接到 C-11 的二-O-乙酰基-β-D-别吡喃糖基部分组成。已从树皮中分离出十培酮苷（10-羟基虹膜苷）。荚膜甙的结构和绝对构型是通过光谱方法确定的，而十倍全甙的结构和绝对构型是通过与阿多糖苷的化学关联确定的。
• Tanaka, Masahide; Kigawa, Masaharu; Mitsuhashi, Hiroshi, Heterocycles, 1991, vol. 32, # 8, p. 1451 - 1454
  作者：Tanaka, Masahide、Kigawa, Masaharu、Mitsuhashi, Hiroshi、Wakamatsu, Takeshi

  DOI：——

  日期：——
• [EN] GENIPIN DERIVATIVES AND USES THEREOF<br/>[FR] DERIVES DE GENIPINE ET LEURS UTILISATIONS
  申请人：BETH ISRAEL HOSPITAL

  公开号：WO2004089926A3

  公开（公告）日：2005-06-30
• Stereoselective Hydrogenation and Ozonolysis of Iridoids. Conversion into Carbocyclic Nucleoside Analogues
  作者：Henrik Franzyk、Frank R. Stermitz

  DOI：10.1021/np990288+

  日期：1999.12.1

  Stereoselective hydrogenation of the iridoids geniposide (9) and aucubin (19) was achieved by using the 1-methyl-1-methoxyethyl ether as a protecting group for the allylic alcohol, as it enhanced the stereoselectivity and prevented undesired hydrogenolysis. Ozonolysis of the hydrogenation product from 9, adoxoside (11), with reductive workup, afforded either a chiral lactone (25) or a chiral polyol (26), depending on the reduction conditions. Polyol 26 was subjected to protecting-group manipulation and subsequent oxidation and reductions to yield cyclopentane building blocks (29-34), which, by Mitsunobu couplings with purines, afforded carbocyclic nucleoside analogues (7, 8, and 35).