6-O-β-D-glucopyranosylcodeine | 32670-64-7

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 吗啡烷
• 英文名称: 6-O-β-D-glucopyranosylcodeine
• 英文别名: (2R,3R,4S,5S,6R)-2-[[(4R,4aR,7S,7aR,12bS)-9-methoxy-3-methyl-2,4,4a,7,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 32670-64-7
• 化学式: C₂₄H₃₁NO₈
• 分子量: 461.512
• InChiKey: NQJIVPDFVAPUAE-YDFBKXKDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  33
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  121
• 氢给体数：
  4
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  可待因 在 silver carbonate 、 lithium hydroxide 作用下， 以 甲醇 、 水 、 苯 为溶剂， 反应 26.0h， 生成 6-O-β-D-glucopyranosylcodeine
  参考文献：
  名称：

  Glucosides of morphine derivatives: synthesis and characterization

  摘要：

  Six 3-O- and 6-O-glucosides of morphine and codeine derivatives were synthesized by means of glucosylation with acetobromo-alpha-d-glucose. O-Glucosylation at C6 was carried out by the Koenigs-Knorr method, whereas the 3-O-glycoside of morphine was synthesized directly upon stirring morphine with acetobromo-alpha-d-glucose and aqueous sodium hydroxide in acetone. Complete H-1 and C-13 NMR assignments are presented for each synthesized compound based on one- and two-dimensional homo- and heteronuclear NMR techniques. Circular dichroism, ultraviolet absorbance, and high-resolution mass spectroscopy data ensure identification and structural characterization of the O-glucoside conjugates. The synthesized glucoside conjugates are potential analgesics; the presented spectral and chromatographic data are useful references for various analytical and metabolic studies including samples of biological origin.

  DOI：

  10.1007/s00706-012-0868-4

文献信息

• Synthesis and Characterization of 6-O-a- and 6-O-b-D-Glucopyranosylmorphine and 6-O-b-D-Glucopyranosylcodeine
  作者：Pavol Kovác、Kenner C. Rice

  DOI：10.3987/com-94-6957

  日期：——

  6-O-alpha- and beta-D-glucopyranosylmorphine and 6-O-beta-D-glucopyranosylcodeine have been prepared by condensations of 2,3,4,6-tetra-O-acyl-alpha-D-glucopyranosyl bromides with 3-O-acetylmorphine and codeine, respectively, followed by deprotection. Depending upon the method of condensation, variable amounts of orthoesters were found among the final products of condensation together with the desired glycosides. Highest yields of glycosides were obtained when 2,3,4,6-tetra-O-benzoyl-alpha-D-glucopyranosyl bromide was the glycosyl donor, and when the condensation was promoted with silver triflate in the presence of a less than stoichiometric amount of 2,4,6-trimethylpyridine as the acid scavenger.
• Casparis et al., Pharmaceutica Acta Helvetiae, 1949, vol. 24, p. 145,146, 152
  作者：Casparis et al.

  DOI：——

  日期：——
• A synthesis of morphine-6-glucuronide
  作者：Christopher Lacy、Malcolm Sainsbury

  DOI：10.1016/0040-4039(95)00649-w

  日期：1995.5

  A practical synthesis of morphine-6-glucuronide from 3-acetylmorphine and methyl 2-alpha-bromo-3,4,5-tri-O-acetylglucuronate is described. Similar syntheses of codeine-6-glucuronide, codeine-6-glucoside and morphine-6-glucoside are also documented
• Glucosides of morphine derivatives: synthesis and characterization
  作者：András Váradi、Dóra Lévai、Gergő Tóth、Péter Horváth、Béla Noszál、Sándor Hosztafi

  DOI：10.1007/s00706-012-0868-4

  日期：2013.2

  Six 3-O- and 6-O-glucosides of morphine and codeine derivatives were synthesized by means of glucosylation with acetobromo-alpha-d-glucose. O-Glucosylation at C6 was carried out by the Koenigs-Knorr method, whereas the 3-O-glycoside of morphine was synthesized directly upon stirring morphine with acetobromo-alpha-d-glucose and aqueous sodium hydroxide in acetone. Complete H-1 and C-13 NMR assignments are presented for each synthesized compound based on one- and two-dimensional homo- and heteronuclear NMR techniques. Circular dichroism, ultraviolet absorbance, and high-resolution mass spectroscopy data ensure identification and structural characterization of the O-glucoside conjugates. The synthesized glucoside conjugates are potential analgesics; the presented spectral and chromatographic data are useful references for various analytical and metabolic studies including samples of biological origin.