2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl 3β-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)lup-20(29)-en-28-oate | 202137-96-0

• 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: 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl 3β-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)lup-20(29)-en-28-oate
• 英文别名: [(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl] (1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-5a,5b,8,8,11a-pentamethyl-1-prop-1-en-2-yl-9-[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysene-3a-carboxylate
• CAS: 202137-96-0
• 化学式: C₅₈H₈₄O₂₁
• 分子量: 1117.29
• InChiKey: NFHYITHEZFSZEO-YQAGAXSLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.3
• 重原子数：
  79
• 可旋转键数：
  24
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  264
• 氢给体数：
  0
• 氢受体数：
  21

反应信息

• 作为反应物：
  描述：

  2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl 3β-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)lup-20(29)-en-28-oate 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 反应 5.0h， 以74.4%的产率得到betulinic acid 3-O-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of Glycosides of Lupane-Type Triterpene Acids

  摘要：

  A preparative synthesis of glucosides of the lupane-type triterpene acids betulinic, dihydrobetulinic, betulonic, dihydrobetulonic. and 3,20-dioxo-30-norlupan-28-oic was proposed. Glycosylation of 3-hydroxyacids by alpha-acetohronioglucose (ABG) with Ag2O was performed in pyridine (Py) to form glycosides at C-28, repeated glycosylation of which by these same reagents but in CH2Cl2 generated a glycoside bond at C-3 to form bisglucosides 28- Glucosides of ketoacids were formed in high yields in both Py and CH2Cl2.

  DOI：

  10.1023/b:conc.0000018113.79735.34
• 作为产物：
  描述：

  白桦脂醇-3-乙酸酯 在 吡啶 、 氢氧化钾 、 tBuOCrO3H 、 silver(l) oxide 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 51.0h， 生成 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl 3β-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)lup-20(29)-en-28-oate
  参考文献：
  名称：

  Synthesis of Glycosides of Lupane-Type Triterpene Acids

  摘要：

  A preparative synthesis of glucosides of the lupane-type triterpene acids betulinic, dihydrobetulinic, betulonic, dihydrobetulonic. and 3,20-dioxo-30-norlupan-28-oic was proposed. Glycosylation of 3-hydroxyacids by alpha-acetohronioglucose (ABG) with Ag2O was performed in pyridine (Py) to form glycosides at C-28, repeated glycosylation of which by these same reagents but in CH2Cl2 generated a glycoside bond at C-3 to form bisglucosides 28- Glucosides of ketoacids were formed in high yields in both Py and CH2Cl2.

  DOI：

  10.1023/b:conc.0000018113.79735.34

文献信息

• Glycosylation of Triterpene Alcohols and Acids of the Lupane and A-Secolupane Series
  作者：Eva Klinotová、Václav Křeček、Jiří Klinot、Magdalena Endová、Jana Eisenreichová、Miloš Buděšínský、Martin Štícha

  DOI：10.1135/cccc19971776

  日期：——

  A series of 3- and 28-glucosides and glucosyl esters of betulinic acid (1a), 28-hydroxy-3,4-secolupa-4(23),20(29)-dien-3-oic acid (22a), dimethyl ester of 28-hydroxy-2,3-secolup-20(29)-en-2,3-dioic acid (43a), their 20(29)-dihydro derivatives (1b, 22b, 43b) and several other triterpenes of the lupane (12a, 12b) and 3,4-secolupane series (18a, 18b, 32a) has been prepared by reaction of tetra-O-acetyl-α-D-glucopyranosyl bromide in acetonitrile in the presence of mercury(II) cyanide and subsequent deacetylation of the obtained tetra-O-acetyl-β-D-glucopyranosyl derivatives. In several cases attempted glucosylation in the presence of silver silicate afforded predominantly the corresponding 1,2-orthoacetates of α-D-glucopyranose.

  一系列3-和28-葡萄糖苷和葡萄糖酯的萜烯酸（1a），28-羟基-3,4-环戊二烯-3-酸（22a），28-羟基-2,3-环戊烷-20-二烯-2,3-二酸二甲酯（43a），它们的20（29）-二氢衍生物（1b，22b，43b）和几种其他狼毒萜烯（12a，12b）和3,4-环戊烷系列（18a，18b，32a）已经通过在乙腈中存在汞（II）氰化物的情况下反应四个-O-乙酰-α-D-葡萄糖吡喃溴化物，并随后脱乙酰化所得的四个-O-乙酰-β-D-葡萄糖吡喃衍生物制备。在几种情况下，尝试在银硅酸盐存在下进行葡萄糖化主要得到相应的α-D-葡萄糖吡喃的1,2-正交醋酸酯。
• BETULINIC ACID AND DERIVATIVES THEREOF USEFUL FOR THE TREATMENT OF NEUROECTODERMAL TUMORS
  申请人：Deutsches KrebsforschungszentrumStiftung des öffentlichen Rechts

  公开号：EP1124842A1

  公开（公告）日：2001-08-22
• US6369109B1
  申请人：——

  公开号：US6369109B1

  公开（公告）日：2002-04-09
• [EN] BETULINIC ACID AND DERIVATIVES THEREOF USEFUL FOR THE TREATMENT OF NEUROECTODERMAL TUMORS<br/>[FR] ACIDE BETULINIQUE ET DERIVES DE CET ACIDE POUR LE TRAITEMENT DE TUMEURS NEUROECTODERMIQUES
  申请人：DEUTSCHES KREBSFORSCH

  公开号：WO2000024762A1

  公开（公告）日：2000-05-04

  The present invention is, generally, directed to the use of betulinic acid and derivatives thereof for the treatment of neuroectodermal tumors. The present invention is based on the discovery that betulinic acid and its deriatives are potent anti-neuroectodermal agents. As disclosed herein, betulinic acid and its derivatives are useful for the treatment of neurodectodermal tumors, including, due to its distinct mechanism of action, neuroectodermal tumors that are resistant to conventional chemotherapeutical agents. In addition to the new use of known compounds, the invention discloses novel compounds and pharmaceutical compositions for the treatment of neuroectodermal tumors.