3,4,5,7-tetra-O-benzyl-1,2,6-trideoxy-6-phthalimido-D-galacto-hept-1-enitol | 169767-83-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 3,4,5,7-tetra-O-benzyl-1,2,6-trideoxy-6-phthalimido-D-galacto-hept-1-enitol
• 英文别名: 2-[(2R,3S,4R,5S)-1,3,4,5-tetrakis(phenylmethoxy)hept-6-en-2-yl]isoindole-1,3-dione
• CAS: 169767-83-3
• 化学式: C₄₃H₄₁NO₆
• 分子量: 667.802
• InChiKey: NZJNRTPODVYCIZ-PFRLLMPSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.81
• 重原子数：
  50.0
• 可旋转键数：
  18.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  74.3
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  3,4,5,7-tetra-O-benzyl-1,2,6-trideoxy-6-phthalimido-D-galacto-hept-1-enitol 在 一水合肼 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成
  参考文献：
  名称：

  α- and β-Homogalactonojirimycins (α- and β-Homogalactostatins) synthesis and further biological evaluation

  摘要：

  The homoiminosugars alpha- and beta -homogalactonojirimycins were prepared from a common intermediate, tetra-O-benzyl-D-galacto-heptenitol 6, by way of highly stereoselective reaction sequences involving, as the key steps, an internal amidomercuralion (a-epimer) and a double reductive amination (beta -epimer). alpha -Homogalactonojirimycin retains a large part of the potent activity of the parent galactonojirimycin and 1-deoxygalactonojirimycin as an inhibitor of alpha -galaclosidases. However, by contrast with the parent iminosugars, it does not inhibit beta -galactosidases, with the exception of the Jack beans enzyme. beta -Homogalactonojirimycin is a weak cc-galactosidase inhibitor and is completely devoid of activity towards P-galactosidases. Thus, a marked selectivity toward one family of enzymes has been achieved by the addition of an alpha -CH2OH group in the structure of the parent iminosugars. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00343-6
• 作为产物：
  描述：

  3,4,5,7-tetra-O-benzyl-1,2-dideoxy-6-O-(4-nitrobenzoyl)-L-altro-hept-1-enitol 在 sodium methylate 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 5.0h， 生成 3,4,5,7-tetra-O-benzyl-1,2,6-trideoxy-6-phthalimido-D-galacto-hept-1-enitol
  参考文献：
  名称：

  α- and β-Homogalactonojirimycins (α- and β-Homogalactostatins) synthesis and further biological evaluation

  摘要：

  The homoiminosugars alpha- and beta -homogalactonojirimycins were prepared from a common intermediate, tetra-O-benzyl-D-galacto-heptenitol 6, by way of highly stereoselective reaction sequences involving, as the key steps, an internal amidomercuralion (a-epimer) and a double reductive amination (beta -epimer). alpha -Homogalactonojirimycin retains a large part of the potent activity of the parent galactonojirimycin and 1-deoxygalactonojirimycin as an inhibitor of alpha -galaclosidases. However, by contrast with the parent iminosugars, it does not inhibit beta -galactosidases, with the exception of the Jack beans enzyme. beta -Homogalactonojirimycin is a weak cc-galactosidase inhibitor and is completely devoid of activity towards P-galactosidases. Thus, a marked selectivity toward one family of enzymes has been achieved by the addition of an alpha -CH2OH group in the structure of the parent iminosugars. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00343-6

文献信息

• Synthesis of “α-Homogalactostatin” and of its 1,N-anhydro derivative
  作者：Olivier R. Martin、Fang Xie、Li Liu

  DOI：10.1016/0040-4039(95)00708-k

  日期：1995.6

  alpha-Homogalactostatin 2 was prepared in 10 steps from 2,3,4,6-tetra-O-benzyl-D-galactose by way of a Wittig chain extension and a mercuricyclization. The synthesis of 2 was assisted by the unexpected participation of the nitrogen protecting group (benzyl carbamate) during iododemercuration. Intermediate 10 was converted in 2 steps into the 1,N-anhydro derivative of 2, compound 3, a potential inactivator of galactosidases.