methyl 3-O-(3,4-di-O-acetyl-2,6-dideoxy-2-iodo-α-L-mannopyranosyl)-3β-hydroxy-11-oxo-18β-olean-12-ene-20β-carboxylate | 188859-48-5

• 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-(3,4-di-O-acetyl-2,6-dideoxy-2-iodo-α-L-mannopyranosyl)-3β-hydroxy-11-oxo-18β-olean-12-ene-20β-carboxylate
• 英文别名: methyl (2S,4aS,6aR,6aS,6bR,8aR,10S,12aS,14bR)-10-[(2R,3R,4R,5S,6S)-4,5-diacetyloxy-3-iodo-6-methyloxan-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: 188859-48-5
• 化学式: C₄₁H₆₁IO₉
• 分子量: 824.834
• InChiKey: FOKXABMXXGJMLG-XXTBDEHRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.4
• 重原子数：
  51
• 可旋转键数：
  8
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  114
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  methyl 3-O-(3,4-di-O-acetyl-2,6-dideoxy-2-iodo-α-L-mannopyranosyl)-3β-hydroxy-11-oxo-18β-olean-12-ene-20β-carboxylate 在 palladium on activated charcoal 氢气 、 三乙胺 作用下， 以 甲醇 为溶剂， 反应 216.0h， 以92.3%的产率得到methyl 3-O-(3,4-di-O-acetyl-2,6-dideoxy-α-L-arabino-hexopyranosyl)-3β-hydroxy-11-oxo-18β-olean-12-ene-20β-carboxylate
  参考文献：
  名称：

  Stereoselective synthesis of 2,6-dideoxy-?-l-arabino-hexopyranoside of glycyrrhetic acid in the presence of iodine-containing promoters

  摘要：

  Glycosylation of methyl glycyrrhetate with L-rhamnal acetate in the presence of iodine-containing promoters and subsequent hydrogenolysis yield 2,6-dideoxy-alpha-L-arabino-hexopyranoside of glycyrrhetic acid, an analog of glycyrrhizic acid, the natural glycoside of licorice foot extract.

  DOI：

  10.1007/bf01430657
• 作为产物：
  描述：

  (3beta,20beta)-3-羟基-11-氧代-齐墩果-12-烯-29-酸甲酯 、 3,4-二-O-乙酰-1,5-酐-2,6-双脱氧-L-阿拉伯-己-1-糖醇 在 iodonium di(2,4,6-trimethylpyridine) perchlorate 、 4 A molecular sieve 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以84%的产率得到methyl 3-O-(3,4-di-O-acetyl-2,6-dideoxy-2-iodo-α-L-mannopyranosyl)-3β-hydroxy-11-oxo-18β-olean-12-ene-20β-carboxylate
  参考文献：
  名称：

  Stereoselective synthesis of 2,6-dideoxy-?-l-arabino-hexopyranoside of glycyrrhetic acid in the presence of iodine-containing promoters

  摘要：

  Glycosylation of methyl glycyrrhetate with L-rhamnal acetate in the presence of iodine-containing promoters and subsequent hydrogenolysis yield 2,6-dideoxy-alpha-L-arabino-hexopyranoside of glycyrrhetic acid, an analog of glycyrrhizic acid, the natural glycoside of licorice foot extract.

  DOI：

  10.1007/bf01430657