乙基N-{[{[(2,2-二甲基-2,3-二氢-1-苯并呋喃-7-基)氧代]羰基}(甲基)氨基]硫烷基}-N-己基-β-丙氨酸酸酯 | 28591-01-7

• 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
• 中文名称: 乙基N-{[{[(2,2-二甲基-2,3-二氢-1-苯并呋喃-7-基)氧代]羰基}(甲基)氨基]硫烷基}-N-己基-β-丙氨酸酸酯
• 中文别名: 支脱皂苷
• 英文名称: β-D-glucopyranosyl-(1-> 2)-β-D-xylopyranosyl-(1-> 3)-β-D-glucopyranosyl-(1-> 4)-β-D-galactopyranosyl-(1-> 3)-(25R)-5α-spirostan-2α,3β-diol
• 英文别名: (25R)-5α-spirostan-2α,3β-diol 3-O-[β-D-glucopyranosyl-(1->2)-[β-D-xylopyranosyl-(1->3)]-β-D-glucopyranosyl-(1->4)]-β-D-galactopyranoside；(25R)-2α-hydroxy-5α-spirostan-3β-yl β-D-glucopyranosyl-(1→2)-[β-D-xylopyranosyl-(1→3)]-β-D-glucopyranosyl-(1→4)-β-D-galactopyranoside；gitogenin 3-O-{O-β-D-glucopyranosyl-(1->2)-O-[β-D-xylopyranosyl-(1->3)]-O-β-D-glucopyranosyl-(1->4)-β-D-galactopyranoside}；6-deoxyaginoside；F-gitonin；(2S,3R,4S,5S,6R)-2-[(2S,3R,4S,5R,6R)-2-[(2R,3R,4R,5R,6R)-4,5-dihydroxy-2-(hydroxymethyl)-6-[(1R,2S,4S,5'R,6R,7S,8R,9S,12S,13S,15R,16R,18S)-15-hydroxy-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosane-6,2'-oxane]-16-yl]oxyoxan-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)-4-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 28591-01-7
• 化学式: C₅₀H₈₂O₂₃
• 分子量: 1051.19
• InChiKey: AULWDENWMBJIIQ-KHXIKGBRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  73
• 可旋转键数：
  11
• 环数：
  10.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  355
• 氢给体数：
  13
• 氢受体数：
  23

反应信息

• 作为反应物：
  描述：

  乙基N-{[{[(2,2-二甲基-2,3-二氢-1-苯并呋喃-7-基)氧代]羰基}(甲基)氨基]硫烷基}-N-己基-β-丙氨酸酸酯 在 硫酸 作用下， 以 乙醇 为溶剂， 反应 2.0h， 生成 支脱皂苷元
  参考文献：
  名称：

  Steroidal glycosides from Allium cyrillii bulbs

  摘要：

  在 Allium cyrillii Ten.鳞茎。利用化学和光谱分析方法确定了这些苷的结构为：β-D-吡喃葡萄糖基-(1 → 2)-[β-D-吡喃木糖基-(1 → 3)]-β-D-吡喃葡萄糖基-(1 → 4)β-D 吡喃半乳糖基-(1 → 3)-(25R)-5α-螺甾烷-2α、3β-二醇和β-D-吡喃葡萄糖基-(1 → 2)-[4-O-(3-羟基-3-甲基戊二酰)-β-D-吡喃木糖基-(1 → 3)]-β-D-吡喃葡萄糖基-(1 → 4)-β-D-吡喃半乳糖基-(1 → 3)-(25R)-5α-螺甾烷-2α,3β-二醇。

  DOI：

  10.1007/s10600-012-0219-z
• 作为产物：
  描述：

  gitogenin 3-O-3)-O-β-D-glucopyranosyl-(1->2)-O-<β-D-xylopyranosyl-(1->3)>-O-β-D-glucopyranosyl-(1->4)-β-D-galactopyranoside> 在 β-glucosidase 作用下， 以 水 为溶剂， 反应 10.0h， 以35.8 mg的产率得到乙基N-{[{[(2,2-二甲基-2,3-二氢-1-苯并呋喃-7-基)氧代]羰基}(甲基)氨基]硫烷基}-N-己基-β-丙氨酸酸酯
  参考文献：
  名称：

  Steroidal glycosides of gitogenin from Allium rotundum

  摘要：

  通过对薤白花序和花茎中提取的总物质进行分馏，分离出了两种新的甾体苷。根据化学转化、物理常数和光谱数据，确定其结构为 26-O-β-D-吡喃葡萄糖基-(25R)-5α-呋喃甾2α,3β,22α、26-tetraol 3-O-β-D-glucopyranosyl-(1 → 2)[β-D-xylopyranosyl-(1 → 3)]-β-D-glucopyranosyl(1 → 4)-β-D-galactopyranoside (2) 和 (25R)-5α-spirostan-2α、3β-diol 3-O-β-D-吡喃葡萄糖基-(1 → 3)-βD-吡喃葡萄糖基-(1 → 2)-[β-D-吡喃木糖基-(1 → 3)]-β-D-吡喃葡萄糖基-(1 → 4)-β-D-吡喃半乳糖苷 (3)。

  DOI：

  10.1007/s10600-012-0164-x

文献信息

• The steroidal glycosides of the flowers of Yucca gloriosa
  作者：Kimiko Nakano、Emi Matsuda、Kaori Tsurumi、Tokushi Yamasaki、Kotaro Murakami、Yoshihisa Takaishi、Toshiaki Tomimatsu

  DOI：10.1016/0031-9422(88)80033-5

  日期：1988.1

  Abstract Four steroidal compounds were isolated from the fresh flowers of Yucca gloriosa and their structures were elucidated as tigogenin 3-O-β- d -xylopyranosyl-β-lycotetraoside, gitogenin 3-O-β- d -xylopyranosyl-β-lycotetraoside, gitogenin 3-O-α- l -rhamnopyranosyl-β-lycotetraoside and proto-type of gitogenin 3-O-β- d -xylopyranosyl-β-lycotetraoside, on the basis of physical and chemical investigations

  摘要 从兰兰鲜花中分离得到4种甾体化合物，并阐明了其结构为：tigogenin 3-O-β-d-吡喃木糖基-β-lycotetraoside、gitogenin 3-O-β-d-xylopyranosyl-β-lycotetraoside、gitogenin 3-O-α-l -rhamnopyranosyl-β-lycotetraoside 和 gitogenin 3-O-β-d -xylopyranosyl-β-lycotetraoside 的原型，基于物理和化学研究。
• Steroidal glycosides from Allium cyrillii bulbs
  作者：N. V. Tolkacheva、A. S. Shashkov、V. Ya Chirva

  DOI：10.1007/s10600-012-0219-z

  日期：2012.5

  Two spirostanol saponins, one of which was a new compound, were isolated among the steroidal glycosides of Allium cyrillii Ten. Bulbs. The structures of these glycosides were established using chemical and spectral analytical methods as β-D-glycopyranosyl-(1 → 2)-[β-D-xylopyranosyl-(1 → 3)]-β-D-glucopyranosyl-(1 → 4)β-D-galactopyranosyl-(1 → 3)-(25R)-5α-spirostan-2α,3β-diol and β-D-glucopyranosyl-(1 → 2)-[4-O-(3hydroxy-3-methylglutaryl)-β-D-xylopyranosyl-(1 → 3)]-β-D-glucopyranosyl-(1 → 4)-β-D-galactopyranosyl(1 → 3)-(25R)-5α-spirostan-2α,3β-diol.

  在 Allium cyrillii Ten.鳞茎。利用化学和光谱分析方法确定了这些苷的结构为：β-D-吡喃葡萄糖基-(1 → 2)-[β-D-吡喃木糖基-(1 → 3)]-β-D-吡喃葡萄糖基-(1 → 4)β-D 吡喃半乳糖基-(1 → 3)-(25R)-5α-螺甾烷-2α、3β-二醇和β-D-吡喃葡萄糖基-(1 → 2)-[4-O-(3-羟基-3-甲基戊二酰)-β-D-吡喃木糖基-(1 → 3)]-β-D-吡喃葡萄糖基-(1 → 4)-β-D-吡喃半乳糖基-(1 → 3)-(25R)-5α-螺甾烷-2α,3β-二醇。
• Steroidal glycosides of gitogenin from Allium rotundum
  作者：M. R. Maisashvili、Dzh. K. Kuchukhidze、V. S. Kikoladze、L. N. Gvazava

  DOI：10.1007/s10600-012-0164-x

  日期：2012.3

  Two new steroidal glycosides were isolated by fractionation of total extracted substances from inflorescences and flower stalks of Allium rotundum (Alliaceae). The structures were determined on the basis of chemical transformations, physical constants, and spectral data as 26-O-β-D-glucopyranosyl-(25R)-5α-furostan2α,3β,22α,26-tetraol 3-O-β-D-glucopyranosyl-(1 → 2)[β-D-xylopyranosyl-(1 → 3)]-β-D-glucopyranosyl(1 → 4)-β-D-galactopyranoside (2) and (25R)-5α-spirostan-2α,3β-diol 3-O-β-D-glucopyranosyl-(1 → 3)-βD-glucopyranosyl-(1 → 2)-[β-D-xylopyranosyl-(1 → 3)]-β-D-glucopyranosyl-(1 → 4)-β-D-galactopyranoside (3).

  通过对薤白花序和花茎中提取的总物质进行分馏，分离出了两种新的甾体苷。根据化学转化、物理常数和光谱数据，确定其结构为 26-O-β-D-吡喃葡萄糖基-(25R)-5α-呋喃甾2α,3β,22α、26-tetraol 3-O-β-D-glucopyranosyl-(1 → 2)[β-D-xylopyranosyl-(1 → 3)]-β-D-glucopyranosyl(1 → 4)-β-D-galactopyranoside (2) 和 (25R)-5α-spirostan-2α、3β-diol 3-O-β-D-吡喃葡萄糖基-(1 → 3)-βD-吡喃葡萄糖基-(1 → 2)-[β-D-吡喃木糖基-(1 → 3)]-β-D-吡喃葡萄糖基-(1 → 4)-β-D-吡喃半乳糖苷 (3)。