methyl 3-O-[2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-acetyl-β-D-galactopyranosyl]-18β-glycyrrhetinate | 163849-62-5

• 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: methyl 3-O-[2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-acetyl-β-D-galactopyranosyl]-18β-glycyrrhetinate
• 英文别名: methyl (2S,4aS,6aR,6aS,6bR,8aR,10S,12aS,14bR)-10-[(2R,3R,4S,5R,6R)-3,4-diacetyloxy-6-(acetyloxymethyl)-5-[(2S,3R,4S,5S,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-2,4a,6a,6b,9,9,12a-heptamethyl-13-oxo-3,4,5,6,6a,7,8,8a,10,11,12,14b-dodecahydro-1H-picene-2-carboxylate
• CAS: 163849-62-5
• 化学式: C₅₇H₈₂O₂₁
• 分子量: 1103.27
• InChiKey: DFVIDKCQMZJDIK-LGXYHVGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  78
• 可旋转键数：
  22
• 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：

  methyl 3-O-[2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-acetyl-β-D-galactopyranosyl]-18β-glycyrrhetinate 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 以82.7%的产率得到methyl β-D-galactopyranosyl-(1->4)-β-D-glucopyranosyl-3-O-18β-glycyrrhetinate
  参考文献：
  名称：

  Synthetic studies on the relationship between anti-HIV activities and micelle forming abilities of various alkylated glycyrrhetinate diglycoside sodium sulfates and related compounds

  摘要：

  Sodium sulfates 11-14, 29-32, 35 and 37 of various alkyl glycyrrhizin and related compounds were synthesized. In vitro anti-HIV activities of the sulfates were compared to the activities of glycyrrhizin 1 in the inhibition of replications of HTLV-III and GUN-4. The activities of the sulfates were increased 11.1, 15.2, 9.1 and 5.0 times for 11-14, 100.0, 125.5, 83.3 and 11.6 times for 29-32, and 11.6 and 50.0 times for 35 and 37. From the relationship between CMC values and anti-HIV activities of the sulfates, it appeared that the sulfates exhibiting more potent antiviral activities had higher micelle forming abilities. Sodium sulfates having a triterpenoid or steroid ring in the molecule showed more potent activities than those of thioglycosides which had no such ring. From the investigation of syncytium formation, we suggest that the active sulfates inhibited HIV-1 infection early in the replication cycle of the virus.

  DOI：

  10.1016/0223-5234(96)89163-x
• 作为产物：
  描述：

  (3beta,20beta)-20-羧基-11-氧代-30-去甲齐墩果-12-烯-3-基 2-O-beta-D-吡喃葡糖基-beta-D-吡喃葡糖苷酸 在 calcium sulfate 、 氢氧化钾 、 硫酸 、 silver carbonate 作用下， 以 甲醇 、 乙醚 、 乙醇 、 二氯甲烷 为溶剂， 反应 55.0h， 生成 methyl 3-O-[2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-acetyl-β-D-galactopyranosyl]-18β-glycyrrhetinate
  参考文献：
  名称：

  Synthetic studies on the relationship between anti-HIV activities and micelle forming abilities of various alkylated glycyrrhetinate diglycoside sodium sulfates and related compounds

  摘要：

  Sodium sulfates 11-14, 29-32, 35 and 37 of various alkyl glycyrrhizin and related compounds were synthesized. In vitro anti-HIV activities of the sulfates were compared to the activities of glycyrrhizin 1 in the inhibition of replications of HTLV-III and GUN-4. The activities of the sulfates were increased 11.1, 15.2, 9.1 and 5.0 times for 11-14, 100.0, 125.5, 83.3 and 11.6 times for 29-32, and 11.6 and 50.0 times for 35 and 37. From the relationship between CMC values and anti-HIV activities of the sulfates, it appeared that the sulfates exhibiting more potent antiviral activities had higher micelle forming abilities. Sodium sulfates having a triterpenoid or steroid ring in the molecule showed more potent activities than those of thioglycosides which had no such ring. From the investigation of syncytium formation, we suggest that the active sulfates inhibited HIV-1 infection early in the replication cycle of the virus.

  DOI：

  10.1016/0223-5234(96)89163-x

文献信息

• Efficient synthesis of glycyrrhetinic acid glycoside/glucuronide derivatives using silver zeolite as promoter
  作者：Maria Carmen del Ruiz Ruiz、Hassan Amer、Christian Stanetty、Igor Beseda、Laszlo Czollner、Priti Shah、Ulrich Jordis、Bernhard Kueenburg、Dirk Claßen-Houben、Andreas Hofinger、Paul Kosma

  DOI：10.1016/j.carres.2009.04.015

  日期：2009.6

  good yields. The ester protecting group located at C-30 of the oleanolic acid scaffold exerted an influence on the overall yield, with the methylester-protected glycosyl acceptor giving better yields compared to the allyl, benzyl as well as diphenylmethyl ester aglycon. The acetyl-protected glucuronides were differently deblocked in high yields via Zemplén deacetylation or via hydrogenolysis followed

  使用糖基溴化物供体和银沸石作为促进剂，以高至高收率和出色的立体选择性合成了甘草次酸的3-O-甘氨酸。除了制备含有β-连接的葡糖基，2-脱氧-2-三氯乙酰氨基-葡糖基，半乳糖基，纤维二糖基和乳糖基残基的糖苷外，还可以将失活的乙酰化的葡糖基吡喃葡萄糖基脲酸酯溴化物供体与三萜糖苷配基酯衍生物良好地偶联。位于齐墩果酸支架的C-30处的酯保护基团对总收率产生影响，与烯丙基，苄基以及二苯基甲基酯糖苷配基相比，由甲基酯保护的糖基受体给出了更好的收率。分别通过Zemplén脱乙酰化或通过氢解，然后通过Zemplén脱乙酰化和碱性水解，分别以高收率对乙酰基保护的葡糖醛酸苷进行解封，以使酯基分别选择性地从葡糖醛酸苷或甘草次酸单元中释放出来。目标糖苷/葡糖醛酸苷用作药物研究的探针，旨在确定糖苷/葡糖醛酸苷三萜的结构-活性关系。