4-[(3R,5R)-2-benzyl-5-(methoxycarbonyl)-3-isoxazolidinyl]-3-O-benzyl-1,2-O-isopropylidene-α-D-xylo-tetrofuranose | 649571-81-3

• 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: 4-[(3R,5R)-2-benzyl-5-(methoxycarbonyl)-3-isoxazolidinyl]-3-O-benzyl-1,2-O-isopropylidene-α-D-xylo-tetrofuranose
• 英文别名: (3R,5R)-2-benzyl-3-(3-O-benzyl-1,2-O-isopropylidene-α-D-xylo-tetrofuranos-4-yl)-5-(methoxycarbonyl)isoxazolidene；methyl (3R,5R)-3-[(3aR,5R,6S,6aR)-2,2-dimethyl-6-phenylmethoxy-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-2-benzyl-1,2-oxazolidine-5-carboxylate
• CAS: 649571-81-3
• 化学式: C₂₆H₃₁NO₇
• 分子量: 469.535
• InChiKey: AFNIQTLVLHTQLG-UVGMCDDHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  34
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  75.7
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  4-[(3R,5R)-2-benzyl-5-(methoxycarbonyl)-3-isoxazolidinyl]-3-O-benzyl-1,2-O-isopropylidene-α-D-xylo-tetrofuranose 在 氨 、 水 、 lithium 、 溶剂黄146 、 锌 作用下， 以 四氢呋喃 为溶剂， 反应 7.0h， 生成 4-[(3R,5R)-3-hydroxy-2-oxo-5-pyrrolidinyl]-1,2-O-isopropylidene-α-D-xylo-tetrofuranose
  参考文献：
  名称：

  1,3-Dipolar cycloaddition between N-benzyl-C-glycosyl nitrones and methyl acrylate en route to glycosyl pyrrolidines

  摘要：

  1,3-Dipolar cycloaddition reactions between three N-benzyl-C-glycosyl nitrones and methyl acrylate afforded key intermediates for the synthesis of glycosyl pyrrolidines. The best result was obtained with a D-galactose derived nitrone which afforded only one isomer in quantitative yield. Absolute configurations were assigned by applying the Kakisawa's rule and X-ray diffraction methods. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2003.08.027
• 作为产物：
  描述：

  丙烯酸甲酯（MA） 、 (Z)-N-benzyl-(3-O-benzyl-1,2-O-isopropylidene-α-D-xylofuranos-5-ylidene)amine N-oxide 以 甲苯 为溶剂， 反应 14.0h， 以33%的产率得到4-[(3R,5R)-2-benzyl-5-(methoxycarbonyl)-3-isoxazolidinyl]-3-O-benzyl-1,2-O-isopropylidene-α-D-xylo-tetrofuranose
  参考文献：
  名称：

  Efficient synthesis of 2,6,7,8-tetrahydroxyindolizidines (castanospermine analogues) via the dipolar cycloadditions of N-benzyl-C-(tetrofuranos-4-yl)nitrones to methyl acrylate

  摘要：

  The dipolar cycloaddition of (Z) -N-benzyl-(3-O-benzy]-1,2-O-isopropylidene-alpha-D-ribofuranos-5-ylidene)amin e N-oxide to methyl acrylate gives a 53:16:26:5 diastereomeric mixture of isoxazolidine derivatives. The dipolar cycloaddition of the xylo analogue to methyl acrylate is more diastereoselective, producing a 44:13:43 mixture of only three diastereomers. The ribo-configured adducts have been converted (4 steps only) into the new (2R,6S,7S,8R,8aR)-, (2S,6S,7S,8R,8aR)-, (2S,6S,7S,8R,8aS)- and (2R,6S,7S,8R,8aS)-2,6,7,8-tetrahydroxyindolizidines. Similarly, the two xylo-configured major isoxazolidine derivatives were converted into the known derivatives (2R,6S,7R,8R,8aS)- and (2S,6S,7R,8R,8aR)-2,6,7,8-tetrahydroxyindolizidines. The six isomeric indolizidine derivatives obtained have been evaluated for their inhibiting activities towards 15 glycosidases. Only the (2R,6S,7S,8R,8aR)-configured isomer is a selective inhibitor of amyloglucosidases from Aspergillus niger (IC50 = 350 mu M) and,from Rhizopus mold (IC50 = 90 mu M, K-i = 195 mu M, non-competitive), the other indolizidines show very little inhibitory activity at 1 mM concentration. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.08.001

文献信息

• 1,3-Dipolar cycloaddition between N-benzyl-C-glycosyl nitrones and methyl acrylate en route to glycosyl pyrrolidines
  作者：Pedro Merino、Santiago Franco、Francisco L. Merchan、Pilar Romero、Tomas Tejero、Santiago Uriel

  DOI：10.1016/j.tetasy.2003.08.027

  日期：2003.11

  1,3-Dipolar cycloaddition reactions between three N-benzyl-C-glycosyl nitrones and methyl acrylate afforded key intermediates for the synthesis of glycosyl pyrrolidines. The best result was obtained with a D-galactose derived nitrone which afforded only one isomer in quantitative yield. Absolute configurations were assigned by applying the Kakisawa's rule and X-ray diffraction methods. (C) 2003 Elsevier Ltd. All rights reserved.
• Efficient synthesis of 2,6,7,8-tetrahydroxyindolizidines (castanospermine analogues) via the dipolar cycloadditions of N-benzyl-C-(tetrofuranos-4-yl)nitrones to methyl acrylate
  作者：Ma Isabel Torres-Sánchez、Pastora Borrachero、Francisca Cabrera-Escribano、Manuel Gómez-Guillén、Manuel Angulo-Álvarez、Eleuterio Álvarez、Sylvain Favre、Pierre Vogel

  DOI：10.1016/j.tetasy.2007.08.001

  日期：2007.8

  The dipolar cycloaddition of (Z) -N-benzyl-(3-O-benzy]-1,2-O-isopropylidene-alpha-D-ribofuranos-5-ylidene)amin e N-oxide to methyl acrylate gives a 53:16:26:5 diastereomeric mixture of isoxazolidine derivatives. The dipolar cycloaddition of the xylo analogue to methyl acrylate is more diastereoselective, producing a 44:13:43 mixture of only three diastereomers. The ribo-configured adducts have been converted (4 steps only) into the new (2R,6S,7S,8R,8aR)-, (2S,6S,7S,8R,8aR)-, (2S,6S,7S,8R,8aS)- and (2R,6S,7S,8R,8aS)-2,6,7,8-tetrahydroxyindolizidines. Similarly, the two xylo-configured major isoxazolidine derivatives were converted into the known derivatives (2R,6S,7R,8R,8aS)- and (2S,6S,7R,8R,8aR)-2,6,7,8-tetrahydroxyindolizidines. The six isomeric indolizidine derivatives obtained have been evaluated for their inhibiting activities towards 15 glycosidases. Only the (2R,6S,7S,8R,8aR)-configured isomer is a selective inhibitor of amyloglucosidases from Aspergillus niger (IC50 = 350 mu M) and,from Rhizopus mold (IC50 = 90 mu M, K-i = 195 mu M, non-competitive), the other indolizidines show very little inhibitory activity at 1 mM concentration. (C) 2007 Elsevier Ltd. All rights reserved.