2-{(2R,6S)-6-[(2R,4R,5S)-7-((2S,6R)-6-Allyl-tetrahydro-pyran-2-yl)-2,4-dihydroxy-5-methyl-heptyl]-tetrahydro-pyran-2-yl}-2-methyl-propionic acid benzyl ester | 404890-44-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-{(2R,6S)-6-[(2R,4R,5S)-7-((2S,6R)-6-Allyl-tetrahydro-pyran-2-yl)-2,4-dihydroxy-5-methyl-heptyl]-tetrahydro-pyran-2-yl}-2-methyl-propionic acid benzyl ester
• 英文别名: benzyl 2-[(2R,6S)-6-[(2R,4R,5S)-2,4-dihydroxy-5-methyl-7-[(2S,6R)-6-prop-2-enyloxan-2-yl]heptyl]oxan-2-yl]-2-methylpropanoate
• CAS: 404890-44-4
• 化学式: C₃₂H₅₀O₆
• 分子量: 530.745
• InChiKey: HJPYYOQPIVWYQJ-FZUZVKDXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  38
• 可旋转键数：
  15
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  85.2
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-{(2R,6S)-6-[(2R,4R,5S)-7-((2S,6R)-6-Allyl-tetrahydro-pyran-2-yl)-2,4-dihydroxy-5-methyl-heptyl]-tetrahydro-pyran-2-yl}-2-methyl-propionic acid benzyl ester 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 吡啶 、 咪唑 、 4-二甲氨基吡啶 、 potassium phosphate 、 氟化氢吡啶 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 36.0h， 生成 2-{(2R,6S)-6-[(1S,13S,15R,16S,19S)-15-(tert-Butyl-dimethyl-silanyloxy)-9-hydroxy-16-methyl-11-oxo-12,23-dioxa-tricyclo[17.3.1.0^5,10]tricosa-5(10),6,8-trien-13-ylmethyl]-tetrahydro-pyran-2-yl}-2-methyl-propionic acid benzyl ester
  参考文献：
  名称：

  A Concise Synthesis of (+)-SCH 351448

  摘要：

  yWe describe a highly convergent synthetic approach to the natural product (+)-SCH 351448 (1)-a hexane-soluble heptacoordinate monosodium salt of a C-2-symmetrical macrocyclic dilactone. Our approach implements a photochemical acylation as the key step to combine two nearly identical but orthogonal C1-C29 fragments, followed by a base-induced intramolecular acylation and deprotection to yield the natural product.

  DOI：

  10.1021/ol0510769
• 作为产物：
  描述：

  Thiocarbonic acid O-[(1R,2S)-1-((2S,6R)-6-allyl-tetrahydro-pyran-2-ylmethyl)-3-((1R,5S,7S)-10,10-dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]dec-4-yl)-2-methyl-3-oxo-propyl] ester O-phenyl ester 在 lithium aluminium tetrahydride 、 偶氮二异丁腈 、 三正丁基氢锡 、 戴斯-马丁氧化剂 、 三乙胺 、 diethylboron trifluoromethanesulfonate 作用下， 以 乙醚 、 正己烷 、 二氯甲烷 、 苯 为溶剂， 反应 11.0h， 生成 2-{(2R,6S)-6-[(2R,4R,5S)-7-((2S,6R)-6-Allyl-tetrahydro-pyran-2-yl)-2,4-dihydroxy-5-methyl-heptyl]-tetrahydro-pyran-2-yl}-2-methyl-propionic acid benzyl ester
  参考文献：
  名称：

  Synthesis of the C1−C21 (C1‘-C21‘) Fragment of the Dimeric Polyketide Natural Product SCH 351448

  摘要：

  A convergent, stereoselective assembly of the C1-C21 (Cl'-C21') fragment of SCH 351448, a 28-membered bis-lactose natural product, has been developed. A highly efficient approach to this fragment assembles 75% of the carbon skeleton and all the stereochemical elements present in the natural product. In addition, an interesting boron ligand effect on the diastereoselectivity of a key aldol reaction with methyl ketone-derived enolborinates is reported.

  DOI：

  10.1021/ol016938u

文献信息

• Synthesis of the C1−C21 (C1‘-C21‘) Fragment of the Dimeric Polyketide Natural Product SCH 351448
  作者：Ashoke Bhattacharjee、Omid Soltani、Jef K. De Brabander

  DOI：10.1021/ol016938u

  日期：2002.2.1

  A convergent, stereoselective assembly of the C1-C21 (Cl'-C21') fragment of SCH 351448, a 28-membered bis-lactose natural product, has been developed. A highly efficient approach to this fragment assembles 75% of the carbon skeleton and all the stereochemical elements present in the natural product. In addition, an interesting boron ligand effect on the diastereoselectivity of a key aldol reaction with methyl ketone-derived enolborinates is reported.
• A Concise Synthesis of (+)-SCH 351448
  作者：Omid Soltani、Jef K. De Brabander

  DOI：10.1021/ol0510769

  日期：2005.6.1

  yWe describe a highly convergent synthetic approach to the natural product (+)-SCH 351448 (1)-a hexane-soluble heptacoordinate monosodium salt of a C-2-symmetrical macrocyclic dilactone. Our approach implements a photochemical acylation as the key step to combine two nearly identical but orthogonal C1-C29 fragments, followed by a base-induced intramolecular acylation and deprotection to yield the natural product.