2-benzyloxy-6-{(16R)-[3,4,6-tri-O-benzyl-5-O-tert-butyldimethylsilyl-D-gluconoyloxy]heptadecyl}benzoic acid benzyl ester | 205693-52-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-benzyloxy-6-{(16R)-[3,4,6-tri-O-benzyl-5-O-tert-butyldimethylsilyl-D-gluconoyloxy]heptadecyl}benzoic acid benzyl ester
• 英文别名: benzyl 2-[(16R)-16-[(2R,3R,4S,5R)-5-[tert-butyl(dimethyl)silyl]oxy-2-hydroxy-3,4,6-tris(phenylmethoxy)hexanoyl]oxyheptadecyl]-6-phenylmethoxybenzoate
• CAS: 205693-52-3
• 化学式: C₇₁H₉₄O₁₀Si
• 分子量: 1135.61
• InChiKey: KYDCTCGIZSSXNM-FQRDGHTQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  16.7
• 重原子数：
  82
• 可旋转键数：
  42
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  119
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  2-benzyloxy-6-{(16R)-[3,4,6-tri-O-benzyl-5-O-tert-butyldimethylsilyl-D-gluconoyloxy]heptadecyl}benzoic acid benzyl ester 在 吡啶 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.25h， 生成 2-benzyloxy-6-{(16R)-[2-O-acetyl-3,4,6-tri-O-benzyl-5-O-tert-butyldimethylsilyl-D-mannonoyloxy]heptadecyl}benzoic acid benzyl ester
  参考文献：
  名称：

  Total Synthesis of Caloporoside

  摘要：

  The first total synthesis of the fungal metabolite caloporoside 1, a strong and selective inhibitor of phospholipase C, is described. Both sugar units of its complex disaccharidic segment were obtained from 3,4,6-tri-O-benzyl-D-glucopyranose 14 as a common building block, with D-gluco-->D-manno inversions as the key strategic elements. This particular substitution reaction occurred readily on the acyclic segment (27-->28), whereas ultrasonication was required to override adverse stereoelectronic effects upon formation of beta-D-mannopyranoside unit 34. The (16R)-hydroxyheptadecylsalicylic acid part of 1 was efficiently prepared by a palladium-catalyzed Suzuki cross coupling reaction of aryltriflate 7 with the 9-alkyl-9-BBN derivative formed from alkene 6 and 9-H-9-BBN.

  DOI：

  10.1021/jo9800098
• 作为产物：
  描述：

  3,4,6-tri-O-benzyl-D-glucopyranose 在 咪唑 、 4-二甲氨基吡啶 、 sodium chlorite 、 sodium tetrahydroborate 、 硼烷四氢呋喃络合物 、 草酰氯 、 1-氯-N,N,2-三甲基丙烯胺 、 3 A molecular sieve 、 硫酸 、 氨基磺酸 、 二甲基亚砜 、 三乙胺 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 反应 43.67h， 生成 2-benzyloxy-6-{(16R)-[3,4,6-tri-O-benzyl-5-O-tert-butyldimethylsilyl-D-gluconoyloxy]heptadecyl}benzoic acid benzyl ester
  参考文献：
  名称：

  Total Synthesis of Caloporoside

  摘要：

  The first total synthesis of the fungal metabolite caloporoside 1, a strong and selective inhibitor of phospholipase C, is described. Both sugar units of its complex disaccharidic segment were obtained from 3,4,6-tri-O-benzyl-D-glucopyranose 14 as a common building block, with D-gluco-->D-manno inversions as the key strategic elements. This particular substitution reaction occurred readily on the acyclic segment (27-->28), whereas ultrasonication was required to override adverse stereoelectronic effects upon formation of beta-D-mannopyranoside unit 34. The (16R)-hydroxyheptadecylsalicylic acid part of 1 was efficiently prepared by a palladium-catalyzed Suzuki cross coupling reaction of aryltriflate 7 with the 9-alkyl-9-BBN derivative formed from alkene 6 and 9-H-9-BBN.

  DOI：

  10.1021/jo9800098

文献信息

• Total Synthesis of Caloporoside
  作者：Alois Fürstner、Ingo Konetzki

  DOI：10.1021/jo9800098

  日期：1998.5.1

  The first total synthesis of the fungal metabolite caloporoside 1, a strong and selective inhibitor of phospholipase C, is described. Both sugar units of its complex disaccharidic segment were obtained from 3,4,6-tri-O-benzyl-D-glucopyranose 14 as a common building block, with D-gluco-->D-manno inversions as the key strategic elements. This particular substitution reaction occurred readily on the acyclic segment (27-->28), whereas ultrasonication was required to override adverse stereoelectronic effects upon formation of beta-D-mannopyranoside unit 34. The (16R)-hydroxyheptadecylsalicylic acid part of 1 was efficiently prepared by a palladium-catalyzed Suzuki cross coupling reaction of aryltriflate 7 with the 9-alkyl-9-BBN derivative formed from alkene 6 and 9-H-9-BBN.