(2R,3R,4S,5S)-2-(allyloxy)-5-((R)-2-(benzoyloxy)-1-(((2R,3R,4S,5S)-3,4-diacetoxy-5-((R)-1,2-diacetoxyethyl)tetrahydrofuran-2-yl)oxy)ethyl)tetrahydrofuran-3,4-diyl dibenzoate | 1236300-06-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3R,4S,5S)-2-(allyloxy)-5-((R)-2-(benzoyloxy)-1-(((2R,3R,4S,5S)-3,4-diacetoxy-5-((R)-1,2-diacetoxyethyl)tetrahydrofuran-2-yl)oxy)ethyl)tetrahydrofuran-3,4-diyl dibenzoate
• CAS: 1236300-06-3
• 化学式: C₄₄H₄₆O₁₈
• 分子量: 862.838
• InChiKey: KLBADVNEPWUAMH-KJYSESJTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.69
• 重原子数：
  62.0
• 可旋转键数：
  19.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  221.02
• 氢给体数：
  0.0
• 氢受体数：
  18.0

反应信息

• 作为反应物：
  描述：

  (2R,3R,4S,5S)-2-(allyloxy)-5-((R)-2-(benzoyloxy)-1-(((2R,3R,4S,5S)-3,4-diacetoxy-5-((R)-1,2-diacetoxyethyl)tetrahydrofuran-2-yl)oxy)ethyl)tetrahydrofuran-3,4-diyl dibenzoate 、 (undec-10-en-1-yloxy)benzene 在 Grubbs catalyst first generation 作用下， 以 二氯甲烷 为溶剂， 反应 17.0h， 以77%的产率得到(2S,3S,4R,5R)-2-((R)-2-(benzoyloxy)-1-(((2R,3R,4S,5S)-3,4-diacetoxy-5-((R)-1,2-diacetoxyethyl)tetrahydrofuran-2-yl)oxy)ethyl)-5-((12-phenoxydodec-2-en-1-yl)oxy)tetrahydrofuran-3,4-diyl dibenzoate
  参考文献：
  名称：

  Synthesis of galactofuranose-based acceptor substrates for the study of the carbohydrate polymerase GlfT2

  摘要：

  Despite the prevalence and importance of carbohydrate polymers, the molecular details of their biosynthesis remain elusive. Many enzymes responsible for the synthesis of carbohydrate polymers require a 'primer' or 'initiator' carbohydrate sequence. One example of such an enzyme is the mycobacterial galactofuranosyltransferase GlfT2 (Rv3808c), which generates an essential cell wall building block. We recently demonstrated that recombinant GlfT2 is capable of producing a polymer composed of alternating beta-(1,5) and beta-(1,6)-linked galactofuranose (Galf) residues. Intriguingly, the length of the polymers produced from a synthetic glycosyl acceptor is consistent with those found in the cell wall. To probe the mechanism by which polymer length is controlled, a collection of initiator substrates has been assembled. The central feature of the synthetic route is a ruthenium-catalyzed cross-metathesis as the penultimate transformation. Access to synthetic substrates has led us to postulate a new mechanism for length control in this template-independent polymerization. Moreover, our investigations indicate that lipids possessing but a single galactofuranose residue can act as substrates for GlfT2. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.04.068
• 作为产物：
  描述：

  allyl 2,3,6-tri-O-benzoyl-β-D-galactofuranoside 、 ethyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-galactofuranoside 在 N-碘代丁二酰亚胺 、 silver trifluoromethanesulfonate 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以55%的产率得到(2R,3R,4S,5S)-2-(allyloxy)-5-((R)-2-(benzoyloxy)-1-(((2R,3R,4S,5S)-3,4-diacetoxy-5-((R)-1,2-diacetoxyethyl)tetrahydrofuran-2-yl)oxy)ethyl)tetrahydrofuran-3,4-diyl dibenzoate
  参考文献：
  名称：

  Synthesis of galactofuranose-based acceptor substrates for the study of the carbohydrate polymerase GlfT2

  摘要：

  Despite the prevalence and importance of carbohydrate polymers, the molecular details of their biosynthesis remain elusive. Many enzymes responsible for the synthesis of carbohydrate polymers require a 'primer' or 'initiator' carbohydrate sequence. One example of such an enzyme is the mycobacterial galactofuranosyltransferase GlfT2 (Rv3808c), which generates an essential cell wall building block. We recently demonstrated that recombinant GlfT2 is capable of producing a polymer composed of alternating beta-(1,5) and beta-(1,6)-linked galactofuranose (Galf) residues. Intriguingly, the length of the polymers produced from a synthetic glycosyl acceptor is consistent with those found in the cell wall. To probe the mechanism by which polymer length is controlled, a collection of initiator substrates has been assembled. The central feature of the synthetic route is a ruthenium-catalyzed cross-metathesis as the penultimate transformation. Access to synthetic substrates has led us to postulate a new mechanism for length control in this template-independent polymerization. Moreover, our investigations indicate that lipids possessing but a single galactofuranose residue can act as substrates for GlfT2. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.04.068