[(2R,3R,4R,5R,6R)-5-[[(2S)-2-[[(2S)-5-[[amino-[(4-methoxy-2,3,6-trimethylphenyl)sulfonylamino]methylidene]amino]-2-(prop-2-ynoylamino)pentanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-2-(azidomethyl)-4-benzoyloxy-6-methoxyoxan-3-yl] benzoate | 857351-82-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: [(2R,3R,4R,5R,6R)-5-[[(2S)-2-[[(2S)-5-[[amino-[(4-methoxy-2,3,6-trimethylphenyl)sulfonylamino]methylidene]amino]-2-(prop-2-ynoylamino)pentanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-2-(azidomethyl)-4-benzoyloxy-6-methoxyoxan-3-yl] benzoate
• CAS: 857351-82-7
• 化学式: C₄₉H₅₅N₉O₁₃S
• 分子量: 1010.09
• InChiKey: IHLTVSINEPMVEJ-DSJFISDQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  72
• 可旋转键数：
  24
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  295
• 氢给体数：
  6
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  [(2R,3R,4R,5R,6R)-5-[[(2S)-2-[[(2S)-5-[[amino-[(4-methoxy-2,3,6-trimethylphenyl)sulfonylamino]methylidene]amino]-2-(prop-2-ynoylamino)pentanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-2-(azidomethyl)-4-benzoyloxy-6-methoxyoxan-3-yl] benzoate 在 copper(l) iodide 作用下， 以 乙腈 为溶剂， 反应 72.0h， 以33%的产率得到[(1R,9S,12S,15R,16R,18R,26S,29S,32R,33R,35R,36R,38R,39R)-36,38,39-tribenzoyloxy-12,29-bis[(4-hydroxyphenyl)methyl]-16,33-dimethoxy-9,26-bis[3-[[N-(4-methoxy-2,3,6-trimethylphenyl)sulfonylcarbamimidoyl]amino]propyl]-7,10,13,24,27,30-hexaoxo-17,34-dioxa-3,4,5,8,11,14,20,21,22,25,28,31-dodecazapentacyclo[30.2.2.215,18.13,6.120,23]tetraconta-4,6(40),21,23(37)-tetraen-35-yl] benzoate
  参考文献：
  名称：

  C₂-Symmetric Macrocyclic Carbohydrate/Amino Acid Hybrids through Copper(I)-Catalyzed Formation of 1,2,3-Triazoles

  摘要：

  An efficient method was developed for the preparation of macrocyclic carbohydrate/amino acid hybrids by macrocyclization with copper(I)-catalyzed 1,2,3-triazole formation. Methyl 2-amino-6-azido-3,4-di-O-benzoyl-2,6-dideoxy-beta-D-glucopyranoside was prepared and coupled to two different N-propiolyl dipeptides (propiolyl-Tyr-Tyr-OH and propiolyl-Arg(Mtr)-Tyr-OH) to obtain bifunctional molecules carrying one azido group and one terminal alkyne. These bifunctional molecules were cyclodimerized using Cu(I)-catalyzed 1,3-dipolar cycloaddition of azides and alkynes to form macrocycles containing two 1,2,3-triazoles. Various cyclization methods were evaluated, and the most efficient conditions were found to be Cul and N,N-diisopropylethylamine in CH3-CN.

  DOI：

  10.1021/jo050585l
• 作为产物：
  描述：

  methyl 6-azido-3,4-di-O-benzoyl-2-(tert-butoxycarbonyl)amino-2,6-dideoxy-β-D-glucopyranoside 在 三乙基硅烷 、 1-羟基苯并三唑 、 三氟乙酸 、 N,N'-二异丙基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 20.0h， 生成 [(2R,3R,4R,5R,6R)-5-[[(2S)-2-[[(2S)-5-[[amino-[(4-methoxy-2,3,6-trimethylphenyl)sulfonylamino]methylidene]amino]-2-(prop-2-ynoylamino)pentanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-2-(azidomethyl)-4-benzoyloxy-6-methoxyoxan-3-yl] benzoate
  参考文献：
  名称：

  C₂-Symmetric Macrocyclic Carbohydrate/Amino Acid Hybrids through Copper(I)-Catalyzed Formation of 1,2,3-Triazoles

  摘要：

  An efficient method was developed for the preparation of macrocyclic carbohydrate/amino acid hybrids by macrocyclization with copper(I)-catalyzed 1,2,3-triazole formation. Methyl 2-amino-6-azido-3,4-di-O-benzoyl-2,6-dideoxy-beta-D-glucopyranoside was prepared and coupled to two different N-propiolyl dipeptides (propiolyl-Tyr-Tyr-OH and propiolyl-Arg(Mtr)-Tyr-OH) to obtain bifunctional molecules carrying one azido group and one terminal alkyne. These bifunctional molecules were cyclodimerized using Cu(I)-catalyzed 1,3-dipolar cycloaddition of azides and alkynes to form macrocycles containing two 1,2,3-triazoles. Various cyclization methods were evaluated, and the most efficient conditions were found to be Cul and N,N-diisopropylethylamine in CH3-CN.

  DOI：

  10.1021/jo050585l