(1R,3R,4S,5R)-3-Azido-4-benzyloxy-6-oxa-bicyclo[3.2.1]octan-8-one | 794535-84-5

• 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: (1R,3R,4S,5R)-3-Azido-4-benzyloxy-6-oxa-bicyclo[3.2.1]octan-8-one
• CAS: 794535-84-5
• 化学式: C₁₄H₁₅N₃O₃
• 分子量: 273.291
• InChiKey: FPPPOYYWBXMPKK-RFHZTLPTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.24
• 重原子数：
  20.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  84.29
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (1R,3R,4S,5R)-3-Azido-4-benzyloxy-6-oxa-bicyclo[3.2.1]octan-8-one 、 (1S,2S,3S,4R,6R)-4-Amino-6-hydroxymethyl-cyclohexane-1,2,3-triol; hydrochloride 在 sodium cyanoborohydride 、 magnesium sulfate 作用下， 以 甲醇 、 水 为溶剂， 生成 (1S,2S,3S,4R,6R)-4-((1S,3R,4S,5S,8R)-3-Azido-4-benzyloxy-6-oxa-bicyclo[3.2.1]oct-8-ylamino)-6-hydroxymethyl-cyclohexane-1,2,3-triol
  参考文献：
  名称：

  Synthesis of 5a-carba-hexopyranoses and hexopyranosylamines, as well as 5a,5a′-dicarbadisaccharides, from 3,8-dioxatricyclo[4.2.1.02,4]nonan-9-ol: glycosidase inhibitory activity of N-substituted 5a-carba-β-gluco- and β-galactopyranosylamines, and derivatives thereof

  摘要：

  Since glycosidase and glycosyltransferase inhibitors, composed of carba-sugars, have recently attracted much attention, it is desirable to develop effective preparative routes for provision of new carba-sugar derivatives of potential biological interest. 1,2:3,6-Dianhydro-5a-carba-alpha-glucopyranose was here chosen for study of synthetic utility, and demonstrated to be a promising intermediate for supplying several carba-beta-glycosylamines and N-linked dicarba-oligosaccharides. An N-linked 5a,5a'-dicarbalactose derivative obtained here was found to be a strong alpha-galactosidase inhibitor (IC50 1.2muM, green coffee beans). (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.07.091
• 作为产物：
  描述：

  (1S,2S,4S,6R,9R)-9-Methoxymethoxy-3,8-dioxa-tricyclo[4.2.1.0^2,4]nonane 在 盐酸 、 sodium azide 、 乙酸酐 、 二甲基亚砜 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 (1R,3R,4S,5R)-3-Azido-4-benzyloxy-6-oxa-bicyclo[3.2.1]octan-8-one
  参考文献：
  名称：

  Synthesis of 5a-carba-hexopyranoses and hexopyranosylamines, as well as 5a,5a′-dicarbadisaccharides, from 3,8-dioxatricyclo[4.2.1.02,4]nonan-9-ol: glycosidase inhibitory activity of N-substituted 5a-carba-β-gluco- and β-galactopyranosylamines, and derivatives thereof

  摘要：

  Since glycosidase and glycosyltransferase inhibitors, composed of carba-sugars, have recently attracted much attention, it is desirable to develop effective preparative routes for provision of new carba-sugar derivatives of potential biological interest. 1,2:3,6-Dianhydro-5a-carba-alpha-glucopyranose was here chosen for study of synthetic utility, and demonstrated to be a promising intermediate for supplying several carba-beta-glycosylamines and N-linked dicarba-oligosaccharides. An N-linked 5a,5a'-dicarbalactose derivative obtained here was found to be a strong alpha-galactosidase inhibitor (IC50 1.2muM, green coffee beans). (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.07.091

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。