(25R)-3β-(β-D-glucopyranosyloxy)-5α-spirostan-6-one | 123941-68-4

• 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)-3β-(β-D-glucopyranosyloxy)-5α-spirostan-6-one
• 英文别名: (25R)-5α-spirost-6-one-3β-ol 3-O-β-D-glucopyranoside；(25r)-3beta-(beta-d-Glucopyranosyloxy)-5alpha-spirostan-6-one；(1R,2S,4S,5'R,6R,7S,8R,9S,12S,13R,16S,18S)-5',7,9,13-tetramethyl-16-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosane-6,2'-oxane]-19-one
• CAS: 123941-68-4
• 化学式: C₃₃H₅₂O₉
• 分子量: 592.77
• InChiKey: UITMIAGHTWCVOR-NFFVKVTDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  42
• 可旋转键数：
  3
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.97
• 拓扑面积：
  135
• 氢给体数：
  4
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (25R)-3β-(β-D-glucopyranosyloxy)-5α-spirostan-6-one 在 吡啶 、 对甲苯磺酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 laxogenin-3-yl 2,3-O-di-benzoyl-4,6-O-benzylidene-D-glucopyranoside
  参考文献：
  名称：

  Glycosyl Trifluoroacetimidates. 2. Synthesis of Dioscin and Xiebai Saponin I

  摘要：

  Two trisaccharide steroidal saponins, dioscin (1) and Xiebai saponin 1 (2) with various bioactivities, were efficiently synthesized using the newly developed glycosyl N-phenyl trifluoroacetimidates (10-13) as glycosylation donors. Thus, dioscin was synthesized in five steps and a 33% overall yield from diosgenin and glycosyl trifluoroacetimidates (10 and 11). Xiebai saponin I was synthesized in eight steps and a 32% overall yield from laxogenin and glycosyl trifluoroacetimidates (10, 12, and 13), whereupon, the rare steroid laxogenin was prepared from diosgenin in four steps and an overall 69% yield. All the glycosylation reactions involved in the present syntheses demonstrated that glycosyl trifluoroacetimidates were successful donors comparable to the corresponding glycosyl trichloroacetimidates.

  DOI：

  10.1021/jo026103c
• 作为产物：
  描述：

  (25R)-3β-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-5α-spirostan-6-one 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以91%的产率得到(25R)-3β-(β-D-glucopyranosyloxy)-5α-spirostan-6-one
  参考文献：
  名称：

  Synthesis of brassinosteroids analogues from laxogenin and their plant growth promotion

  摘要：

  Four steroid saponins (2-5) and three derivatives (6-8) were synthesised from laxogenin. Four of them were new compounds: (25R)-3 beta-(2,3,4,6-tetra-O-acetyl-beta-d-galactopyranosyloxy)-5 alpha-spirostan-6-one (3), (25R)-3 beta-(beta-d-galactopyranosyloxy)-5 alpha-spirostan-6-one (5), 3 beta,16-diacetyl-26-hydroxy-5 alpha-cholestan-6,22-dione (6) and 16-acetyl-3 beta,26-dihydroxy-5 alpha-cholestan-6,22-dione (7). All the compounds showed plant growth-promoting activity in the radish hypocotyl elongation and cotyledon expansion bioassay. Above all, 2 and 6 were found to be more active.

  DOI：

  10.1080/14786419.2014.968151

文献信息

• Matsuura, Hiromichi; Ushiroguchi, Tsuyoshi; Itakura, Yoichi, Chemical and pharmaceutical bulletin, 1989, vol. 37, # 5, p. 1390 - 1391
  作者：Matsuura, Hiromichi、Ushiroguchi, Tsuyoshi、Itakura, Yoichi、Fuwa, Toru

  DOI：——

  日期：——