benzyl ((2R,3R,4R,5S,6R)-4,5-bis(benzyloxy)-2-(((5S,5aR,8aR,9R)-9-(4-(((benzyloxy)carbonyl)oxy)-3,5-dimethoxyphenyl)-8-oxo-5,5a,6,8,8a,9-hexahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-5-yl)oxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-3-yl)carbamate | 134637-16-4

• 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: benzyl ((2R,3R,4R,5S,6R)-4,5-bis(benzyloxy)-2-(((5S,5aR,8aR,9R)-9-(4-(((benzyloxy)carbonyl)oxy)-3,5-dimethoxyphenyl)-8-oxo-5,5a,6,8,8a,9-hexahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-5-yl)oxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-3-yl)carbamate
• CAS: 134637-16-4
• 化学式: C₆₄H₆₁NO₁₆
• 分子量: 1100.19
• InChiKey: GMUUVHFYOPPYGM-XEFXGXCJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.55
• 重原子数：
  81.0
• 可旋转键数：
  21.0
• 环数：
  11.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  183.23
• 氢给体数：
  1.0
• 氢受体数：
  16.0

反应信息

• 作为反应物：
  描述：

  benzyl ((2R,3R,4R,5S,6R)-4,5-bis(benzyloxy)-2-(((5S,5aR,8aR,9R)-9-(4-(((benzyloxy)carbonyl)oxy)-3,5-dimethoxyphenyl)-8-oxo-5,5a,6,8,8a,9-hexahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-5-yl)oxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-3-yl)carbamate 在 palladium dihydroxide 氢气 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 反应 12.0h， 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：

  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：

  3,4,6-tri-O-benzyloxycarbonylamino-2-deoxy-D-glucopyranose 在 正丁基锂 、 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 1.25h， 生成 benzyl ((2R,3R,4R,5S,6R)-4,5-bis(benzyloxy)-2-(((5S,5aR,8aR,9R)-9-(4-(((benzyloxy)carbonyl)oxy)-3,5-dimethoxyphenyl)-8-oxo-5,5a,6,8,8a,9-hexahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-5-yl)oxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-3-yl)carbamate
  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