1,3,4,5-tetra-O-benzyl-7-O-(t-butyldimethylsilyl)-2,6-dideoxy-2,6-imino-L-glycero-L-galacto-heptitol | 355014-76-5

• 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-7-O-(t-butyldimethylsilyl)-2,6-dideoxy-2,6-imino-L-glycero-L-galacto-heptitol
• CAS: 355014-76-5
• 化学式: C₄₁H₅₃NO₅Si
• 分子量: 667.961
• InChiKey: WETNZVUVNOFXBT-UVEJXLBHSA-N

反应信息

• 作为反应物：
  描述：

  1,3,4,5-tetra-O-benzyl-7-O-(t-butyldimethylsilyl)-2,6-dideoxy-2,6-imino-L-glycero-L-galacto-heptitol 在 溶剂黄146 作用下， 以 四氢呋喃 、 水 为溶剂， 以78%的产率得到1,3,4,5-tetra-O-benzyl-2,6-dideoxy-2,6-imino-L-glycero-L-galacto-heptitol
  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：

  1,3,4,5-tetra-O-benzyl-7-O-(t-butyldimethylsilyl)-L-galacto-heptitol 在 草酰氯 、 3 A molecular sieve 、 ammonium formate 、 sodium cyanoborohydride 、 二甲基亚砜 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 1,3,4,5-tetra-O-benzyl-7-O-(t-butyldimethylsilyl)-2,6-dideoxy-2,6-imino-L-glycero-L-galacto-heptitol
  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