dodecyl 2,4,6-tri-O-acetyl-3-O-benzyl-5a-carba-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside | 504422-57-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: dodecyl 2,4,6-tri-O-acetyl-3-O-benzyl-5a-carba-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside
• CAS: 504422-57-5
• 化学式: C₅₉H₇₈O₁₃
• 分子量: 995.261
• InChiKey: TUGNLDJJWFUCSD-YXRWAAOHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.82
• 重原子数：
  72.0
• 可旋转键数：
  31.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  143.51
• 氢给体数：
  0.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  dodecyl 2,4,6-tri-O-acetyl-3-O-benzyl-5a-carba-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside 在 palladium on activated charcoal 盐酸 、 氢气 、 sodium methylate 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 7.0h， 生成 dodecyl 5a'-carba-β-lactoside
  参考文献：
  名称：

  Synthesis of an ether-linked alkyl 5a-carba-β-d-glucoside, a 5a-carba-β-d-galactoside, a 2-acetamido-2-deoxy-5a-carba-β-d-glucoside, and an alkyl 5a′-carba-β-lactoside

  摘要：

  For the purpose of providing biologically stable building blocks for the biocombinatorial synthesis using a living cell, some ether-linked alkyl 5a-carba-beta-D-glycoside primers were prepared. The key step of the synthesis was coupling of 1-bromo-n-alkanes with the 1-OH unprotected derivatives of 5a-carba-sugar analogues of D-glucose, D-galactose, and 2-acetamido-2-deoxy-D-glucose (N-acetyl-D-glucosamine). in DMF in the presence of sodium hydride. Alternatively, alkyl carba-lactoside was synthesized by incorporation of a 5a-carba-beta-D-galactose residue into the 4-position of dodecyl beta-D-glueopyranoside, A strong and specific inhibition of beta-galactosidase (K-i 0.67 muM bovine liver) was found for dodecyl 5a-carba-beta-D-galactopyranoside. (C) 2002 Elsevier Science Ltd. All rights reserved,

  DOI：

  10.1016/s0008-6215(02)00294-x
• 作为产物：
  描述：

  dodecyl β-D-galactopyranoside 在 吡啶 、 三氯化铝 、 molecular sieve 、 tetrafluoroboric acid-diethyl ether complex 、 15-冠醚-5 、 乙酸酐 、 sodium hydride 、 对甲苯磺酸 、 溶剂黄146 、 二甲基亚砜 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 269.5h， 生成 dodecyl 2,4,6-tri-O-acetyl-3-O-benzyl-5a-carba-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of an ether-linked alkyl 5a-carba-β-d-glucoside, a 5a-carba-β-d-galactoside, a 2-acetamido-2-deoxy-5a-carba-β-d-glucoside, and an alkyl 5a′-carba-β-lactoside

  摘要：

  For the purpose of providing biologically stable building blocks for the biocombinatorial synthesis using a living cell, some ether-linked alkyl 5a-carba-beta-D-glycoside primers were prepared. The key step of the synthesis was coupling of 1-bromo-n-alkanes with the 1-OH unprotected derivatives of 5a-carba-sugar analogues of D-glucose, D-galactose, and 2-acetamido-2-deoxy-D-glucose (N-acetyl-D-glucosamine). in DMF in the presence of sodium hydride. Alternatively, alkyl carba-lactoside was synthesized by incorporation of a 5a-carba-beta-D-galactose residue into the 4-position of dodecyl beta-D-glueopyranoside, A strong and specific inhibition of beta-galactosidase (K-i 0.67 muM bovine liver) was found for dodecyl 5a-carba-beta-D-galactopyranoside. (C) 2002 Elsevier Science Ltd. All rights reserved,

  DOI：

  10.1016/s0008-6215(02)00294-x