12β-acethoxy-3β,20S-dihydroxydammar-24-ene | 127750-92-9

• 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: 12β-acethoxy-3β,20S-dihydroxydammar-24-ene
• 英文别名: [(3S,5R,8R,9R,10R,12R,13R,14R,17S)-3-hydroxy-17-[(2S)-2-hydroxy-6-methylhept-5-en-2-yl]-4,4,8,10,14-pentamethyl-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-12-yl] acetate
• CAS: 127750-92-9
• 化学式: C₃₂H₅₄O₄
• 分子量: 502.778
• InChiKey: LKRKFHZNHGXEGW-PLSKFXFDSA-N

物化性质

• 沸点：
  570.7±40.0 °C(Predicted)
• 密度：
  1.06±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.8
• 重原子数：
  36
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  12β-acethoxy-3β,20S-dihydroxydammar-24-ene 在 sodium methylate 、 silver carbonate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 15.0h， 生成 (2S,3R,4S,5S,6R)-2-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-2-[[(3S,5R,8R,9R,10R,12R,13R,14R,17S)-12-hydroxy-17-[(2S)-2-hydroxy-6-methylhept-5-en-2-yl]-4,4,8,10,14-pentamethyl-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]-6-(hydroxymethyl)oxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
  参考文献：
  名称：

  Synthesis of ginsenoside Rg3, a minor constituent of Ginseng Radix

  摘要：

  Glycosylation of 12 beta-acetoxy-dammar-24-en-3 beta,20(S)-diol (4), with hepta-O-acetyl-alpha-sophorosyl bromide (5) under catalysis by Ag2CO3 or Ag2O afforded a chromatographically unseparated mixture of the alpha-and beta-linked octaacetates 6 and 7 in an approximately 2.5:1 ratio. After deprotection and chromatographic purification, the free alpha- (8) and beta-glycosides (9) were obtained. Sophoroside 9 was identical in all respects with ginsenoside Rg(3), the minor component of Ginseng Radix rubra. All compounds were fully characterized by H-1 and C-13 NMR spectroscopy, (C) 1997 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(97)00217-6
• 作为产物：
  描述：

  12β,20S-dihydroxydammar-24-en-3-one 在 吡啶 、 sodium tetrahydroborate 作用下， 以 异丙醇 为溶剂， 生成 12β-acethoxy-3β,20S-dihydroxydammar-24-ene
  参考文献：
  名称：

  Simplified preparation of the ginsenoside-Rh2 minor saponin from ginseng

  摘要：

  Condensation of the 12-O-acetylderivative of 20(S)-protopanaxadiol [dammar-24-ene-3 beta,12 beta,20(S)-triol] with tetra-O-acetyl-alpha-D-glucopyranosyl bromide in the presence of silver oxide in dichloroethane, followed by deprotection with sodium methoxide in methanol, results in formation of the 3-O-beta-D-glucopyranosyldammar-24-ene-3 beta,12 beta,20(S)-triol identical with natural ginsenoside-Rh-2. The 12-O-acetyl-20(S)-protopanaxadiol is easily prepared from betulafolienetriol via the 3-keto-12-O-acetylderivative followed by NaBH4 reduction. This comparatively simple five-step synthesis makes this hitherto rare ginsenoside relatively accessible. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0008-6215(97)00184-5

文献信息

• Synthesis of 20S-protopanaxadiol β-D-galactopyranosides
  作者：L. N. Atopkina、V. A. Denisenko

  DOI：10.1007/s10600-011-9835-2

  日期：2011.3

  20S-Protopanaxadiol (3β,12β,20S-trihydroxydammar-24-ene) 3-, 12-, and 20-O-β-D-galactopyranosides were synthesized for the first time. Condensation of 12β-acetoxy-3β,20S-dihydroxydammar-24-ene (1) and 2,3,4,6-tetra-O-acetyl-α-D-galactopyranosylbromide (α-acetobromogalactose) (2) under Koenigs–Knorr conditions with subsequent removal of the protecting groups resulted in regio- and stereoselective formation of 20S-protopanaxadiol 3-O-β-D-galactopyranoside, an analog of the natural ginsenoside Rh2. Glycosylation of 12β,20S-dihydroxydammar-24-en-3-one (5) by 2 with subsequent treatment of the reaction products with NaBH4 in isopropanol and deacetylation with NaOMe gave 20S-protopanaxadiol 12- and 20-O-β-Dgalactopyranosides.

  20S-Protopanaxadiol (3β,12β,20S-trihydroxydammar-24-ene) 3-、12-和 20-O-β-D-吡喃半乳糖苷首次被合成。12β-acetoxy-3β,20S-dihydroxydammar-24-ene (1) 和 2,3,4、在柯尼希斯-克诺尔条件下，将 12β-acetoxy-3β,20S-dihydroxydammar-24-ene (1) 和 2,3,4-α-D-galactopyranosylbromide (α-乙酰溴半乳糖) (6-tetra-O-acetyl-α-D-galactopyranosylbromide (2))进行糖基化，然后去除保护基团，可形成具有区域和立体选择性的天然人参皂苷 Rh2 类似物 20S-protopanaxadiol 3-O-β-D-galactopyranoside。用 2 对 12β,20S-二羟基达玛-24-烯-3-酮（5）进行糖基化，然后在异丙醇中用 NaBH4 处理反应产物，再用 NaOMe 进行脱乙酰化，得到 20S 原人参皂苷 12- 和 20-O-β-D-吡喃半乳糖苷。