(4S,5R,4'S,5'R)-5'-{[((4S,5R,4'S,5'R)-5'-Azidomethyl-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]e-5-carbonyl)-amino]-methyl}-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-carboxylic acid methyl ester | 668990-28-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4S,5R,4'S,5'R)-5'-{[((4S,5R,4'S,5'R)-5'-Azidomethyl-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]e-5-carbonyl)-amino]-methyl}-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-carboxylic acid methyl ester
• 英文别名: methyl (4R,5S)-5-[(4S,5R)-5-[[[(4R,5S)-5-[(4S,5R)-5-(azidomethyl)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-1,3-dioxolane-4-carbonyl]amino]methyl]-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-1,3-dioxolane-4-carboxylate
• CAS: 668990-28-1
• 化学式: C₂₅H₄₀N₄O₁₁
• 分子量: 572.613
• InChiKey: SUSWLECUQNORKJ-HARLHBKBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  40
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  144
• 氢给体数：
  1
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  (4S,5R,4'S,5'R)-5'-{[((4S,5R,4'S,5'R)-5'-Azidomethyl-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]e-5-carbonyl)-amino]-methyl}-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-carboxylic acid methyl ester 在 sodium hydroxide 作用下， 以 1,4-二氧六环 为溶剂， 反应 4.0h， 以95%的产率得到(4S,5R,4'S,5'R)-5'-{[((4S,5R,4'S,5'R)-5'-Azidomethyl-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]e-5-carbonyl)-amino]-methyl}-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-carboxylic acid
  参考文献：
  名称：

  Huge (14-, 21-, 28-, 35-, 56- and 70-membered ring) macrocyclic lactams––a novel family of carbopeptoid-cyclodextrins

  摘要：

  Hydrogenation of linear omega-azido-pentafluorophenyl esters gives cyclic peptides containing 14-, 21-, 28-, 35-, 56- and 70-membered ring lactams from oligomers derived from epsilon-amino acids in excellent to moderate yields with a lack of racemisation during the cyclisation step. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.10.103
• 作为产物：
  描述：

  methyl 6-azido-6-deoxy-2,3:4,5-di-O-isopropylidene-D-galactonate 在 钯 氢气 、 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 N,N-二异丙基乙胺 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 生成 (4S,5R,4'S,5'R)-5'-{[((4S,5R,4'S,5'R)-5'-Azidomethyl-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]e-5-carbonyl)-amino]-methyl}-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-carboxylic acid methyl ester
  参考文献：
  名称：

  Cyclo[(6-amino-6-deoxy-d-galactonic acid)4]: a new class of carbopeptoid-cyclodextrin

  摘要：

  The formation of the 28-membered ring cyclo[(6-amino-6-deoxy-D-galactonic acid)(4)] by cyclisation of a protected open chain fully hydroxylated nylon 6 linear tetramer in modest yield provides the first example of a new class of carbopeptoid-cyclodextrin. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.10.104

文献信息

• Cyclo[(6-amino-6-deoxy-d-galactonic acid)4]: a new class of carbopeptoid-cyclodextrin
  作者：Benjamin A. Mayes、Rebecca J.E. Stetz、Christopher W.G. Ansell、George W.J. Fleet

  DOI：10.1016/j.tetlet.2003.10.104

  日期：2004.1

  The formation of the 28-membered ring cyclo[(6-amino-6-deoxy-D-galactonic acid)(4)] by cyclisation of a protected open chain fully hydroxylated nylon 6 linear tetramer in modest yield provides the first example of a new class of carbopeptoid-cyclodextrin. (C) 2003 Elsevier Ltd. All rights reserved.
• Huge (14-, 21-, 28-, 35-, 56- and 70-membered ring) macrocyclic lactams––a novel family of carbopeptoid-cyclodextrins
  作者：Benjamin A Mayes、Lieven Simon、David J Watkin、Christopher W.G Ansell、George W.J Fleet

  DOI：10.1016/j.tetlet.2003.10.103

  日期：2004.1

  Hydrogenation of linear omega-azido-pentafluorophenyl esters gives cyclic peptides containing 14-, 21-, 28-, 35-, 56- and 70-membered ring lactams from oligomers derived from epsilon-amino acids in excellent to moderate yields with a lack of racemisation during the cyclisation step. (C) 2003 Elsevier Ltd. All rights reserved.