4,6-O-benzylidene-2-deoxy-2-nitro-5a-carba-β-D-glucopyranose | 504422-37-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二恶烷
• 英文名称: 4,6-O-benzylidene-2-deoxy-2-nitro-5a-carba-β-D-glucopyranose
• 英文别名: (2R,4aR,6R,7S,8R,8aR)-7-nitro-2-phenyl-4a,5,6,7,8,8a-hexahydro-4H-benzo[d][1,3]dioxine-6,8-diol
• CAS: 504422-37-1
• 化学式: C₁₄H₁₇NO₆
• 分子量: 295.292
• InChiKey: QUFXVPMFEKHDDV-BUCHIQEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  105
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4,6-O-benzylidene-2-deoxy-2-nitro-5a-carba-β-D-glucopyranose 在 Raney nickel T-4 氢气 、 sodium methylate 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、250.0 kPa 条件下， 反应 40.0h， 生成 2-acetamido-4,6-O-benzylidene-2-deoxy-5a-carba-β-D-glucopyranose
  参考文献：
  名称：

  Synthesis of an ether-linked alkyl 5a-carba-β-d-glucoside, a 5a-carba-β-d-galactoside, a 2-acetamido-2-deoxy-5a-carba-β-d-glucoside, and an alkyl 5a′-carba-β-lactoside

  摘要：

  For the purpose of providing biologically stable building blocks for the biocombinatorial synthesis using a living cell, some ether-linked alkyl 5a-carba-beta-D-glycoside primers were prepared. The key step of the synthesis was coupling of 1-bromo-n-alkanes with the 1-OH unprotected derivatives of 5a-carba-sugar analogues of D-glucose, D-galactose, and 2-acetamido-2-deoxy-D-glucose (N-acetyl-D-glucosamine). in DMF in the presence of sodium hydride. Alternatively, alkyl carba-lactoside was synthesized by incorporation of a 5a-carba-beta-D-galactose residue into the 4-position of dodecyl beta-D-glueopyranoside, A strong and specific inhibition of beta-galactosidase (K-i 0.67 muM bovine liver) was found for dodecyl 5a-carba-beta-D-galactopyranoside. (C) 2002 Elsevier Science Ltd. All rights reserved,

  DOI：

  10.1016/s0008-6215(02)00294-x
• 作为产物：
  描述：

  (1S)-2-exo,3-endo-diacetoxy-5-endo-acetoxymethyl-7-oxabicyclo<2.2.1.>heptane 在 sodium periodate 、 硫酸 、 sodium methylate 、 碳酸氢钠 、 对甲苯磺酸 作用下， 以 甲醇 、 水 、 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 反应 41.0h， 生成 4,6-O-benzylidene-2-deoxy-2-nitro-5a-carba-β-D-glucopyranose
  参考文献：
  名称：

  Synthesis of an ether-linked alkyl 5a-carba-β-d-glucoside, a 5a-carba-β-d-galactoside, a 2-acetamido-2-deoxy-5a-carba-β-d-glucoside, and an alkyl 5a′-carba-β-lactoside

  摘要：

  For the purpose of providing biologically stable building blocks for the biocombinatorial synthesis using a living cell, some ether-linked alkyl 5a-carba-beta-D-glycoside primers were prepared. The key step of the synthesis was coupling of 1-bromo-n-alkanes with the 1-OH unprotected derivatives of 5a-carba-sugar analogues of D-glucose, D-galactose, and 2-acetamido-2-deoxy-D-glucose (N-acetyl-D-glucosamine). in DMF in the presence of sodium hydride. Alternatively, alkyl carba-lactoside was synthesized by incorporation of a 5a-carba-beta-D-galactose residue into the 4-position of dodecyl beta-D-glueopyranoside, A strong and specific inhibition of beta-galactosidase (K-i 0.67 muM bovine liver) was found for dodecyl 5a-carba-beta-D-galactopyranoside. (C) 2002 Elsevier Science Ltd. All rights reserved,

  DOI：

  10.1016/s0008-6215(02)00294-x

文献信息

• [EN] SELECTIVE GLYCOSIDASE INHIBITORS AND USES THEREOF<br/>[FR] INHIBITEURS SÉLECTIFS DES GLYCOSIDASES ET LEURS UTILISATIONS
  申请人：UNIV FRASER SIMON

  公开号：WO2011140640A1

  公开（公告）日：2011-11-17

  The invention provides compounds of Formula (I) for selectively inhibiting glycosidases, prodrugs of the compounds, and pharmaceutical compositions including the compounds or prodrugs of the compounds. The invention also provides methods of treating diseases and disorders related to deficiency or overexpression of O-G1cNAcase, accumulation or deficiency of O-G1cNAc.

  本发明提供了用于选择性抑制糖苷酶的式I化合物、该化合物的药物前体以及包含该化合物或该化合物药物前体的药物组合物。本发明还提供了治疗与O-G1cNAcase缺乏或过度表达、O-G1cNAc积累或缺乏相关的疾病和障碍的方法。
• SELECTIVE GLYCOSIDASE INHIBITORS AND USES THEREOF
  申请人：Li Tong-Shuang

  公开号：US20130131044A1

  公开（公告）日：2013-05-23

  The invention provides compounds of Formula (I) for selectively inhibiting glycosidases, prodrugs of the compounds, and pharmaceutical compositions including the compounds or prodrugs of the compounds. The invention also provides methods of treating diseases and disorders related to deficiency or overexpression of O-GlcNAcase, accumulation or deficiency of O-GlcNAc.

  该发明提供了式（I）的化合物，用于选择性地抑制糖苷酶，该化合物的前药以及包括该化合物或该化合物的前药的药物组合物。该发明还提供了治疗与O-GlcNAcase缺乏或过度表达，O-GlcNAc的积累或缺乏相关的疾病和疾病的方法。
• OGAWA, SEIICHIRO;ORIHARA, MASARU, CARBOHYDR. RES., 177,(1988) 199-212
  作者：OGAWA, SEIICHIRO、ORIHARA, MASARU

  DOI：——

  日期：——
• US9120781B2
  申请人：——

  公开号：US9120781B2

  公开（公告）日：2015-09-01