Acetic acid (1S,2S,3S)-2,3,4-triacetoxy-1-{(S)-1-acetoxy-2-[acetyl-((S)-1-phenyl-ethyl)-amino]-ethyl}-butyl ester | 79526-50-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: Acetic acid (1S,2S,3S)-2,3,4-triacetoxy-1-{(S)-1-acetoxy-2-[acetyl-((S)-1-phenyl-ethyl)-amino]-ethyl}-butyl ester
• CAS: 79526-50-4；79549-65-8；79549-66-9；79549-67-0；79549-68-1；79617-01-9；83680-90-4；83680-91-5
• 化学式: C₂₆H₃₅NO₁₁
• 分子量: 537.564
• InChiKey: NJUYONBIJBYUCR-IVEQAMCHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.89
• 重原子数：
  38.0
• 可旋转键数：
  13.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  151.81
• 氢给体数：
  0.0
• 氢受体数：
  11.0

反应信息

• 作为产物：
  描述：

  3β,16α-dihydroxyolean-12-en-23,28-dioic acid 28-O-β-D-glucuronopyranosyl-(1→2)-[β-D-glucopyranosyl-(1→6)]-β-D-glucopyranosyl ester 在 盐酸 、 sodium cyanoborohydride 作用下， 以 1,4-二氧六环 、 乙醇 、 水 为溶剂， 反应 29.0h， 生成 Acetic acid (1S,2S,3S)-2,3,4-triacetoxy-1-{(S)-1-acetoxy-2-[acetyl-((S)-1-phenyl-ethyl)-amino]-ethyl}-butyl ester
  参考文献：
  名称：

  来自 Silene armeria 的齐墩果型三萜皂苷

  摘要：

  从 Silene armeria 的整个植物中分离出 12 种三萜皂苷，包括迄今为止未知的 7 种化合物（即 armerosides AG）。它们的结构是基于广泛的光谱分析和化学方法建立的。从生物合成的角度来看，皂苷元的 C-23 氧化似乎是糖基化途径中的关键因素。

  DOI：

  10.1016/j.phytochem.2016.07.011

文献信息

• DETERMINATION OF CONFIGURATION OF MONOSACCHARIDES BY HPLC ON DIASTEREOISOMERIC 1-DEOXY-1-(<i>N</i>-ACETYL-α-METHYLBENZYLAMINO)ALDITOL ACETATES
  作者：Ryuichi Oshima、Ju Kumanotani

  DOI：10.1246/cl.1981.943

  日期：1981.7.5

  Acyclic diastereoisomers, 1-deoxy-1-(N-acetyl-α-methylbenzylamino)alditol acetates, are readily obtained by reductive amination of sugars with chiral α-methylbenzylamine in the presence of sodium cyanoborohydride. Ten pairs of enantiomers of common monosaccharides are resolved by an adsorption HPLC on the diastereoisomers.

  无环非对映异构体，1-脱氧-1-（N-乙酰基-α-甲基苄氨基）醛醇乙酸酯，在氰基硼氢化钠的存在下，通过手性α-甲基苄胺对糖的还原胺化很容易获得。十对常见单糖的对映异构体通过非对映异构体上的吸附 HPLC 进行拆分。
• Isolation and structural elucidation of novel cholestane glycosides and spirostane saponins from Polygonatum odoratum
  作者：Hong Bai、Wei Li、Huanxin Zhao、Yojiro Anzai、Haiming Li、Huanjie Guo、Fumio Kato、Kazuo Koike

  DOI：10.1016/j.steroids.2013.11.013

  日期：2014.2

  Much attention has been paid to cholestane-type steroidal glycosides because of their importance from the perspectives of both chemical diversity and significant biological activities. A phytochemical investigation of the rhizomes of Polygonatum odoratum (Liliaceae) resulted in the isolation of three novel cholestane-type steroidal glycosides (1-3) with unique Delta(14,16)-unsaturated D-ring structures as well as two novel spirostane-type steroidal saponins (4 and 5) and three known steroidal glycosides (6-8). Their structures were determined by various spectroscopic methods and chemical reactions. Steroidal saponin 7 showed significant antifungal activity against Candida albicans JCM1542 (MIC 3.1 mu g/mL) and Aspergillus fumigatus JCM1738 (MIC 6.3 mu g/mL). (C) 2013 Elsevier Inc All rights reserved.
• Phenolic glycosides from Kaempferia parviflora
  作者：Toshiaki Azuma、Yasuo Tanaka、Hiroe Kikuzaki

  DOI：10.1016/j.phytochem.2008.09.001

  日期：2008.11

  Three phenolic glycosides were isolated together with two known flavonol glycosides from the H2O-soluble fraction of rhizomes of Kaempferia parviflora. Their structures were determined to be rel-(5aS,10bS)-5a,10b-dihydro-1,3,5a,9-tetrahydroxy-8-methoxy-6H-benz[b]indeno[1,2-d]furan-6-one 5a-O-[alpha-L-rhamnopyranosyl-(1 -> 6)-beta-D-glucopyranoside] (1), its rel-5aS,10bR isomer (2), and (2R,3S,4S)-3-O-[alpha-L-rhamnopyranosyl-(1 -> 6)-beta-D-glucopyranosyl]-3'-O-methyl-ent-epicatechin-(2 alpha -> O -> 3,4 alpha -> 4)-(5aS, 10bS)-5a, 10b-dihydro-1,3,5a,9-tetrahydroxy-8-methoxy-6H-benz[b]indeno[1,2-d]furan-6-one 5a-O-[alpha-L-rhamnopyranosyl-(1 -> 6)-beta-D-glucopyranoside] (3). The structures were elucidated on the basis of analyses of chemical and spectroscopic evidence. (C) 2008 Elsevier Ltd. All rights reserved.