(5S,5aR,8aR,9R)-5-[(2R,3R,4R,5S,6R)-3-amino-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-9-(4-hydroxy-3,5-dimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[6,5-f][1,3]benzodioxol-8-one | 111310-71-5

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 木脂素内酯
• 英文名称: (5S,5aR,8aR,9R)-5-[(2R,3R,4R,5S,6R)-3-amino-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-9-(4-hydroxy-3,5-dimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[6,5-f][1,3]benzodioxol-8-one
• CAS: 111310-71-5
• 化学式: C₂₇H₃₁NO₁₂
• 分子量: 561.543
• InChiKey: HJQHSHLBFMLMGE-GCQPXTJUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  40
• 可旋转键数：
  6
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  189
• 氢给体数：
  5
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  乙缩醛 、 (5S,5aR,8aR,9R)-5-[(2R,3R,4R,5S,6R)-3-amino-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-9-(4-hydroxy-3,5-dimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[6,5-f][1,3]benzodioxol-8-one 在 对甲苯磺酸 作用下， 以 乙腈 为溶剂， 反应 1.0h， 生成 1-O-(2-amino-2-deoxy-β-D-glucopyranosyl)-<(-)-1-epipodophyllotoxin>
  参考文献：
  名称：

  A new and general glycosidation method for podophyllum lignan glycosides

  摘要：

  A facile and stereocontrolled construction of beta-glycosidic linkages of podophyllotoxin and 4'-O-demethylepipodophyllotoxin D-glucosides or 4'-O-demethylepipodophyllotoxin 2-amino-2-deoxy-D-glucoside has been achieved by exploiting glycopyranosyl P,P-diphenyl-N-(p-toluene-sulfonyl)phosphinimidate and bis(dimethylamido) phosphate as glycosyl donors, respectively.

  DOI：

  10.1016/s0040-4039(00)74296-1
• 作为产物：
  描述：

  [4-[(5S,5aR,8aR,9R)-5-[(2R,3R,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-(phenylmethoxycarbonylamino)oxan-2-yl]oxy-8-oxo-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[5,6-f][1,3]benzodioxol-9-yl]-2,6-dimethoxyphenyl] benzyl carbonate 生成 (5S,5aR,8aR,9R)-5-[(2R,3R,4R,5S,6R)-3-amino-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-9-(4-hydroxy-3,5-dimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[6,5-f][1,3]benzodioxol-8-one
  参考文献：
  名称：

  UMEZAWA, HAMAO;TAKEUCHI, TOMIO;KONDO, SHINICHI;TANAKA, WATARU;TAKITA, TOM+

  摘要：

  DOI：

文献信息

• A new and general glycosidation method for podophyllum lignan glycosides
  作者：Shun-ichi Hashimoto、Takeshi Honda、Shiro Ikegami

  DOI：10.1016/s0040-4039(00)74296-1

  日期：1991.3

  A facile and stereocontrolled construction of beta-glycosidic linkages of podophyllotoxin and 4'-O-demethylepipodophyllotoxin D-glucosides or 4'-O-demethylepipodophyllotoxin 2-amino-2-deoxy-D-glucoside has been achieved by exploiting glycopyranosyl P,P-diphenyl-N-(p-toluene-sulfonyl)phosphinimidate and bis(dimethylamido) phosphate as glycosyl donors, respectively.
• UMEZAWA, HAMAO;TAKEUCHI, TOMIO;KONDO, SHINICHI;TANAKA, WATARU;TAKITA, TOM+
  作者：UMEZAWA, HAMAO、TAKEUCHI, TOMIO、KONDO, SHINICHI、TANAKA, WATARU、TAKITA, TOM+

  DOI：——

  日期：——