(25R)-5α-spirostan-3β-ol 3-O-β-D-galactopyranoside | 35959-24-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: (25R)-5α-spirostan-3β-ol 3-O-β-D-galactopyranoside
• 英文别名: tigogenyl β-D-galactopyranoside；(25r)-5alpha-spirostan-3beta-ol 3-O-beta-d-galactopyranoside；(2R,3R,4S,5R,6R)-2-(hydroxymethyl)-6-[(1R,2S,4S,5'R,6R,7S,8R,9S,12S,13S,16S,18S)-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosane-6,2'-oxane]-16-yl]oxyoxane-3,4,5-triol
• CAS: 35959-24-1
• 化学式: C₃₃H₅₄O₈
• 分子量: 578.787
• InChiKey: ZNEIIZNXGCIAAL-VZGGSASBSA-N

物化性质

• 沸点：
  695.5±55.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  41
• 可旋转键数：
  3
• 环数：
  7.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  118
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (25R)-5α-spirostan-3β-ol 3-O-β-D-galactopyranoside 在 硫酸 作用下， 反应 12.0h， 生成 剑麻皂素
  参考文献：
  名称：

  Steroid glycosides of the roots ofCapsicum annuum. II. The structure of the capsicosides

  摘要：

  DOI：

  10.1007/bf00598758
• 作为产物：
  描述：

  在 sodium methylate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 2.0h， 生成 (25R)-5α-spirostan-3β-ol 3-O-β-D-galactopyranoside
  参考文献：
  名称：

  First Synthesis of a Digitalis Saponin. Demonstration of the Scope and Limitations of a Convergent Scheme for Branched Oligosaccharide Synthesis by the Logic of Glycal Assembly

  摘要：

  The synthesis of complex glycosides, with branching at C-2, is demonstrated. The key element involves the use of a 1,2-oxirane donor. Upon glycosylation, a C-2 hydroxyl is exposed to serve as the acceptor in the next glycosylation. Branching at C-2 with a beta-linked glycoside at C-1 was not achievable with epoxy 23 donor, but was accomplished with fluoro donor 25, in turn derived from 23. (See 19 + 18 --> 20; 20 + 25 --> 26. Compound 26 was deprotected to complete the first total synthesis of a natural saponin, desgalactotigonin (3)). A limitation in stereospecifity in the use of donor 23 and monoprotected galactal acceptor 28 was also encountered.

  DOI：

  10.1021/ja00126a010

文献信息

• Beshornin and beshornoside, steroidal saponins of Beshorneria yuccoides
  作者：Pavel K. Kintia、Valentin A. Bobeyko、Ivan P. Dragalin、Stepan A. Shvets

  DOI：10.1016/0031-9422(82)80165-9

  日期：1982.1

  Two new saponins beshornin and beshornoside have been isolated from the methanolic extract of Beshorneria yuccoides leaves and their structures elucidated. Beshornin is 3-O-[α- l -rhamnopyranosyl-(1 → 4)-β- d -glucopyranosyl- (1 → 2)-[α- l -rhamnopyranosyl-(1 -+ 4)-P-D-glucopyranosyl-(1 → 3)]-β- d -glucopyranosyl-(1 → 4)-β- d - galactopyranosyl-(25R)-5α-spirostan-3β-ol, whereas beshornoside is 3-O-[α-

  摘要 从丝瓜叶甲醇提取物中分离得到了两种新的皂角甙和皂角甙，并阐明了它们的结构。Beshornin 是 3-O-[α- l -rhamnopyranosyl-(1 → 4)-β-d -glupyranosyl- (1 → 2)-[α- l -rhamnopyranosyl-(1 -+ 4)-PD-glupyranosyl-( 1 → 3)]-β- d -吡喃葡萄糖基-(1 → 4)-β- d - 吡喃半乳糖-(25R)-5α-spirostan-3β-ol，而 beshornoside 是 3-O-[α-l-rhamnopyranosyl- (1 → 4)- β- d )-吡喃糖基-(1 → 2)]-[α-l-吡喃鼠李糖基-(1 → 4)-β-d-吡喃葡萄糖基-(1 → 3)]-β-d-吡喃葡萄糖基- (1 → 4)-β- d -吡喃半乳糖基 26-O-[β- d ]-吡喃葡萄糖基-(25R)-5α-呋喃坦-3β
• Application of the glycal assembly strategy to the synthesis of a branched oligosaccharide: the first synthesis of a complex saponin
  作者：John T. Randolph、Samuel J. Danishefsky

  DOI：10.1021/ja00071a077

  日期：1993.9
• Steroid glycosides of the roots ofCapsicum annuum. II. The structure of the capsicosides
  作者：E. V. Gutsu、P. K. Kintya、G. V. Lazur'evskii

  DOI：10.1007/bf00598758

  日期：——
• First Synthesis of a Digitalis Saponin. Demonstration of the Scope and Limitations of a Convergent Scheme for Branched Oligosaccharide Synthesis by the Logic of Glycal Assembly
  作者：John T. Randolph、Samuel J. Danishefsky

  DOI：10.1021/ja00126a010

  日期：1995.5

  The synthesis of complex glycosides, with branching at C-2, is demonstrated. The key element involves the use of a 1,2-oxirane donor. Upon glycosylation, a C-2 hydroxyl is exposed to serve as the acceptor in the next glycosylation. Branching at C-2 with a beta-linked glycoside at C-1 was not achievable with epoxy 23 donor, but was accomplished with fluoro donor 25, in turn derived from 23. (See 19 + 18 --> 20; 20 + 25 --> 26. Compound 26 was deprotected to complete the first total synthesis of a natural saponin, desgalactotigonin (3)). A limitation in stereospecifity in the use of donor 23 and monoprotected galactal acceptor 28 was also encountered.