1,3,4,5-tetra-O-benzyl-2,6-dideoxy-2,6-imino-D-glycero-L-galacto-heptitol O(7),N-cyclic carbamate | 169872-54-2

• 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: 1,3,4,5-tetra-O-benzyl-2,6-dideoxy-2,6-imino-D-glycero-L-galacto-heptitol O(7),N-cyclic carbamate
• 英文别名: 1,3,4,5-tetra-O-benzyl-2,6-dideoxy-2,6-imino-D-glycero-D-galacto-heptitol O(7),N-cyclic carbamate
• CAS: 169872-54-2
• 化学式: C₃₆H₃₇NO₆
• 分子量: 579.693
• InChiKey: GJNCDUUQVDUVOW-VABIIVNOSA-N

物化性质

• 沸点：
  727.8±60.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

反应信息

• 作为反应物：
  描述：

  1,3,4,5-tetra-O-benzyl-2,6-dideoxy-2,6-imino-D-glycero-L-galacto-heptitol O(7),N-cyclic carbamate 生成 (2R,3S,4R,5S,6R)-2-Hydroxymethyl-1-aza-bicyclo[4.1.0]heptane-3,4,5-triol
  参考文献：
  名称：

  Synthesis of “α-Homogalactostatin” and of its 1,N-anhydro derivative

  摘要：

  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.

  DOI：

  10.1016/0040-4039(95)00708-k
• 作为产物：
  描述：

  1,3,4,5-tetra-O-benzyl-2,6-dideoxy-2,6-(benzyloxycarbonyl)imino-D-glycero-L-galacto-heptitol 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以90%的产率得到1,3,4,5-tetra-O-benzyl-2,6-dideoxy-2,6-imino-D-glycero-L-galacto-heptitol O(7),N-cyclic carbamate
  参考文献：
  名称：

  Synthesis of N-substituted iminosugar derivatives and their immunosuppressive activities

  摘要：

  Several N-alkyl and hydroxyethyl-substituted iminosugar derivatives, including L-altro and D-galacto epimers, were synthesized and the effects of these synthetic iminosugars on proliferation of mouse splenocytes were evaluated in the MTT assay. The experimental data demonstrated that the N-alkylated D-galacto iminosugars showed better inhibitory activities than L-altro analogues, which might hold potential as immunosuppressive agents. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2010.01.021

文献信息

• α- and β-Homogalactonojirimycins (α- and β-Homogalactostatins) synthesis and further biological evaluation
  作者：O Martin

  DOI：10.1016/s0968-0896(00)00343-6

  日期：2001.5

  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.