3,7-anhydro-4,6,8-tri-O-benzyl-5-O-(3-O-benzyl-1,2-O-isopropylidene-α-D-ribofuranosuronyl)-2-deoxy-D-glycero-α-D-talo-octonyl chloride | 1311277-68-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,7-anhydro-4,6,8-tri-O-benzyl-5-O-(3-O-benzyl-1,2-O-isopropylidene-α-D-ribofuranosuronyl)-2-deoxy-D-glycero-α-D-talo-octonyl chloride
• 英文别名: [(2R,3R,4R,5R,6R)-2-(2-chloro-2-oxoethyl)-3,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-4-yl] (3aR,5S,6S,6aR)-2,2-dimethyl-6-phenylmethoxy-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxole-5-carboxylate
• CAS: 1311277-68-5
• 化学式: C₄₄H₄₇ClO₁₁
• 分子量: 787.304
• InChiKey: HZPLMSRNAXJKTQ-PIOOCVNTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  56
• 可旋转键数：
  18
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  117
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  3,7-anhydro-4,6,8-tri-O-benzyl-5-O-(3-O-benzyl-1,2-O-isopropylidene-α-D-ribofuranosuronyl)-2-deoxy-D-glycero-α-D-talo-octonyl chloride 在 potassium carbonate 、 1,2-双(二苯基膦)乙烷 作用下， 以 四氢呋喃 、 对二甲苯 为溶剂， 反应 4.0h， 生成 2,6-anhydro-1,3,5-tri-O-benzyl-7-(O6-benzylguanin-8-yl)-5-O-(3-O-benzyl-1,2-O-isopropylidene-α-D-ribofuranosuronyl)-7-deoxy-D-glycero-D-manno-heptitol
  参考文献：
  名称：

  Towards stable di-carba analogues of guanofosfocins

  摘要：

  Guanofosfocins are strong inhibitors of chitin synthases, but also very prone to hydrolytic cleavage. Two advanced intermediates 15 and 20 for the synthesis of stable di-carba-guanofosfocins were prepared via ester 11. Acylation of the allylic C-glycoside 6 with riburonic acid chloride 10 afforded ester 11 in 79% yield. This ester was converted to 15 in four steps and in 54% yield and to 20 in eight steps and in 20% yield. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.02.102
• 作为产物：
  描述：

  甲基-D-丙噻 在 吡啶 、 4-二甲氨基吡啶 、 sodium chlorite 、 sodium dihydrogenphosphate dihydrate 、 2-甲基-2-丁烯 、 草酰氯 、 三氟甲磺酸三甲基硅酯 、 四丁基碘化铵 、 sodium hydride 、 二正丁基氧化锡 、 N,N-二甲基甲酰胺 作用下， 以 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 乙腈 、 叔丁醇 为溶剂， 反应 3.5h， 生成 3,7-anhydro-4,6,8-tri-O-benzyl-5-O-(3-O-benzyl-1,2-O-isopropylidene-α-D-ribofuranosuronyl)-2-deoxy-D-glycero-α-D-talo-octonyl chloride
  参考文献：
  名称：

  Towards stable di-carba analogues of guanofosfocins

  摘要：

  Guanofosfocins are strong inhibitors of chitin synthases, but also very prone to hydrolytic cleavage. Two advanced intermediates 15 and 20 for the synthesis of stable di-carba-guanofosfocins were prepared via ester 11. Acylation of the allylic C-glycoside 6 with riburonic acid chloride 10 afforded ester 11 in 79% yield. This ester was converted to 15 in four steps and in 54% yield and to 20 in eight steps and in 20% yield. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.02.102

文献信息

• Towards stable di-carba analogues of guanofosfocins
  作者：Jan Duchek、Mu-Hua Huang、Andrea Vasella

  DOI：10.1016/j.tetlet.2011.02.102

  日期：2011.6

  Guanofosfocins are strong inhibitors of chitin synthases, but also very prone to hydrolytic cleavage. Two advanced intermediates 15 and 20 for the synthesis of stable di-carba-guanofosfocins were prepared via ester 11. Acylation of the allylic C-glycoside 6 with riburonic acid chloride 10 afforded ester 11 in 79% yield. This ester was converted to 15 in four steps and in 54% yield and to 20 in eight steps and in 20% yield. (C) 2011 Elsevier Ltd. All rights reserved.