5a-carba-β-L-fucopyranosylamine | 432547-03-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5a-carba-β-L-fucopyranosylamine
• 英文别名: (1R,2R,3R,4S,6R)-4-amino-6-methylcyclohexane-1,2,3-triol
• CAS: 432547-03-0
• 化学式: C₇H₁₅NO₃
• 分子量: 161.201
• InChiKey: SRXWNPSUBPQINT-IECVIRLLSA-N

物化性质

• 沸点：
  272.5±40.0 °C(Predicted)
• 密度：
  1.289±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  86.7
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5a-carba-β-L-fucopyranosylamine 在 溶剂黄146 作用下， 以 水 、 异丙醇 为溶剂， 反应 504005.0h， 生成 N-(5a-carba-β-L-fucopyranos-1-yl)-5a-carba-β-L-fucopyranosylamine
  参考文献：
  名称：

  Synthesis and glycosidase inhibitory activity of some N-substituted 5a-carba-β-fuco- and β-galactopyranosylamines, and selected derivatives

  摘要：

  In the course of chemical modification of alpha-fucosidase inhibitors of 5a-carba-fucopyranosylamine type, an N-dodecyl derivative of the enantiomer 6-deoxy-5a-carba-beta-(D)-galactopyranosylamitie demonstrated very strong inhibition of beta-galactosidase and beta-glucosidase. This finding led us to synthesize corresponding 6-hydroxy compounds, in order to elucidate structure-activity relationships for inhibitors of this type. Among four N-alkyl-5a-carba-beta-(D)-galactopyranosylatnines prepared, the N-octyl derivative could be demonstrated to possess moderate activity toward alpha- and beta-galactosidases, and beta-glucosidase. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.09.023
• 作为产物：
  描述：

  3-O-benzoyl-1,5-anhydro-2,6-dideoxy-4-O-mesyl-5a-carba-DL-arabino-hex-1-enitol 在 palladium on activated charcoal 盐酸 、 sodium azide 、 15-冠醚-5 、 氢气 、 苯甲醇钠 、 间氯过氧苯甲酸 作用下， 以 乙醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 120.0h， 生成 5a-carba-β-L-fucopyranosylamine
  参考文献：
  名称：

  Synthesis of an α-Fucosidase Inhibitor, 5a-Carba-β-l-fucopyranosylamine, and Fucose-Type α- and β-dl-Valienamine Unsaturated Derivatives

  摘要：

  Discovery of a very potent alpha-fucosidase inhibitor 5a-carba-alpha-L-fucopyranosylamine (1) led to preparation of its beta-anomer 4 and the respective unsaturated derivatives, fucose-type alpha- and beta-valienamines (5 and 6), in order to elucidate the structure-activity relationship of carba-aminosugar inhibitors of this kind. Compound 4 was demonstrated to be a potent inhibitor (K-i = 2.0 x 10 (7) M, bovine kidney), possessing ca. one-tenth of the activity of the parent 1. Interestingly, 5 and 6 were found to be rather weak inhibitors. contrary to the expectations based on the activity relationships between the alpha-glucosidase inhibitors. a-glucose-type validamine and valienamine. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00004-5

文献信息

• Synthesis of carbasugar-containing non-glycosidically linked pseudodisaccharides and higher pseudooligosaccharides
  作者：Ian Cumpstey

  DOI：10.1016/j.carres.2009.09.008

  日期：2009.11

  This minireview covers synthetic methods towards carbasugar-containing non-glycosidically linked pseudodisaccharides or higher pseudooligosaccharides. Carbocyclic pyranose mimetics (saturated or unsaturated between C-5 and C-5a) are linked by ether, thioether or amine bridges to carbohydrates or other carbasugars.

  这份简短的综述涵盖了针对含碳水化合物的非糖苷键连接的假二糖或高级假寡糖的合成方法。碳环吡喃糖模拟物（在C-5和C-5a之间饱和或不饱和）通过醚桥，硫醚桥或胺桥连接到碳水化合物或其他Carcarbugars。
• Synthesis of an α-Fucosidase Inhibitor, 5a-Carba-β-l-fucopyranosylamine, and Fucose-Type α- and β-dl-Valienamine Unsaturated Derivatives
  作者：Seiichiro Ogawa、Maiko Watanabe、Ayako Maruyama、Seiichi Hisamatsu

  DOI：10.1016/s0960-894x(02)00004-5

  日期：2002.3

  Discovery of a very potent alpha-fucosidase inhibitor 5a-carba-alpha-L-fucopyranosylamine (1) led to preparation of its beta-anomer 4 and the respective unsaturated derivatives, fucose-type alpha- and beta-valienamines (5 and 6), in order to elucidate the structure-activity relationship of carba-aminosugar inhibitors of this kind. Compound 4 was demonstrated to be a potent inhibitor (K-i = 2.0 x 10 (7) M, bovine kidney), possessing ca. one-tenth of the activity of the parent 1. Interestingly, 5 and 6 were found to be rather weak inhibitors. contrary to the expectations based on the activity relationships between the alpha-glucosidase inhibitors. a-glucose-type validamine and valienamine. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Synthesis and glycosidase inhibitory activity of some N-substituted 5a-carba-β-fuco- and β-galactopyranosylamines, and selected derivatives
  作者：Seiichiro Ogawa、Shigeo Fujieda、Yuko Sakata、Masahiro Ishizaki、Seiichi Hisamatsu、Kensuke Okazaki、Yoriko Ooki、Midori Mori、Masayoshi Itoh、Takashi Korenaga

  DOI：10.1016/j.bmc.2004.09.023

  日期：2004.12

  In the course of chemical modification of alpha-fucosidase inhibitors of 5a-carba-fucopyranosylamine type, an N-dodecyl derivative of the enantiomer 6-deoxy-5a-carba-beta-(D)-galactopyranosylamitie demonstrated very strong inhibition of beta-galactosidase and beta-glucosidase. This finding led us to synthesize corresponding 6-hydroxy compounds, in order to elucidate structure-activity relationships for inhibitors of this type. Among four N-alkyl-5a-carba-beta-(D)-galactopyranosylatnines prepared, the N-octyl derivative could be demonstrated to possess moderate activity toward alpha- and beta-galactosidases, and beta-glucosidase. (C) 2004 Elsevier Ltd. All rights reserved.