1,6-anhydro-4-O-benzyl-2-deoxy-2-C-hydroxymethyl-β-D-glucopyranose | 161302-88-1

• 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: 1,6-anhydro-4-O-benzyl-2-deoxy-2-C-hydroxymethyl-β-D-glucopyranose
• 英文别名: 1,6-anhydro-4-O-benzyl-2-deoxy-2-C-hydroxymethyl-β-D-glucose；1,6-anhydro-2-deoxy-2-C-hydroxymethyl-β-D-glucopyranose；1,6-anhydro-4-O-benzyl-2-deoxy-2-C-hydroxymethyl-beta-D-glucopyranose；(1R,2S,3R,4R,5R)-4-(hydroxymethyl)-2-phenylmethoxy-6,8-dioxabicyclo[3.2.1]octan-3-ol
• CAS: 161302-88-1
• 化学式: C₁₄H₁₈O₅
• 分子量: 266.294
• InChiKey: FZHOZCMBLKRIGI-DHGKCCLASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  68.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1,6-anhydro-4-O-benzyl-2-deoxy-2-C-hydroxymethyl-β-D-glucopyranose 在 palladium on activated charcoal sodium periodate 、 硫酸 、 氨 、 氢气 作用下， 以 乙醇 为溶剂， 20.0~45.0 ℃ 、3.5 MPa 条件下， 反应 19.0h， 生成 (3R,4R,5R)-3-benzyloxy-4-hydroxy-5-hydroxymethyl-piperidine
  参考文献：
  名称：

  Synthesis of isofagomine, a novel glycosidase inhibitor

  摘要：

  DOI：

  10.1016/s0040-4020(01)89351-0
• 作为产物：
  描述：

  1,6-anhydro-4-O-benzyl-2-deoxy-2-C-vinyl-β-D-glucopyranose 在 sodium tetrahydroborate 、 臭氧 作用下， 生成 1,6-anhydro-4-O-benzyl-2-deoxy-2-C-hydroxymethyl-β-D-glucopyranose
  参考文献：
  名称：

  Synthesis of isofagomine, a novel glycosidase inhibitor

  摘要：

  DOI：

  10.1016/s0040-4020(01)89351-0

文献信息

• Synthesis and glycosidase inhibitory activity of noeurostegine—a new and potent inhibitor of β-glucoside hydrolases
  作者：Tina Secher Rasmussen、Henrik Helligsø Jensen

  DOI：10.1039/b918576c

  日期：——

  A new, stable hemi-aminal nor-tropane christened noeurostegine was synthesised in 22 steps from levoglucosan and tested for inhibitory activity against glycoside hydrolases. Sweet almond and Thermotoga maritimaβ-glucosidases, coffee bean α-galactosidase, and Asp. oryzaeβ-galactosidase were inhibited in the low micromolar region but significant tightening of binding to Ki 50 nM for almond β-glucosidase

  新型稳定的半尿道 正烷 从12个步骤合成了洗净后的神经营养素 左旋葡聚糖并测试了对糖苷水解酶的抑制活性。甜杏仁和maritoma martoimaβ-葡萄糖苷酶，咖啡豆α-半乳糖苷酶和Asp。稻米β-半乳糖苷酶在低微摩尔区受到抑制，但与之的结合显着增强ķ我预孵育后发现杏仁n-葡萄糖苷酶的浓度为50 nM。酵母α-葡萄糖苷酶和大肠杆菌β-半乳糖苷酶在1 mM时未受到抑制。
• Synthesis of the first pseudosugar-C-disaccharide. A potential antigen for eliciting glycoside-bond forming antibodies with catalytic groups
  作者：Christel Barbaud、Mikael Bols、Inge Lundt、Michael R. Sierks

  DOI：10.1016/0040-4020(95)00505-3

  日期：1995.8

  A number of synthetic routes to the first pseudo-C-disaccharide ever prepared has been studied. The compound, methyl 7-((1S,3R,4R,5S,6S)-1-amino-3-hydroxymethyl-4,5,6trihydroxycyclohexyl) -6,7-dideoxy-α-D-gluco-heptopyranoside (1), is structurally related to cellobiose, but includes a crucial amino-functionality at the pseudoanomeric centre. It was prepared by 1,2-addition of the anion of methyl 6

  已经研究了许多制备第一个假C-二糖的合成途径。化合物7-（（（1S，3R，4R，5S，6S）-1-氨基-3-羟甲基-4,5,6三羟基环己基）-6,7-二脱氧-α-D-葡萄糖-庚基吡喃糖苷（1）与纤维二糖在结构上相关，但在假异构中心具有关键的氨基功能。它是通过将1,6,7-二脱氧-2,3,4-三-O-苄基-α-D-葡萄糖-庚基-6吡喃吡喃果糖苷的阴离子1,2-加成到（4R，5S，6R）-3-苄氧基甲基-4,5,6-三苄氧基-2-环己烯酮，然后将叔醇立体选择性转化为叠氮化物，最后还原。
• Glycohydrolase inhibitors, their preparation and use thereof
  申请人：University of Maryland Baltimore County

  公开号：US05844102A1

  公开（公告）日：1998-12-01

  A compound of the formula ##STR1## wherein n, m, and p, which may be the same or different, are a number between 0 and 5; q is a number between 0 and 10; R.sub.1, R.sub.2 R.sub.3 R.sub.4 and R.sub.5, which may be the same or different, are a hydrogen, a hydroxyl, a halogen, a hydrocarbon or an O-hydrocarbon group having between 1 and 6 carbons which is aliphatic, alicyclic or aromatic, or a glycosyl group; and R.sub.4 is a glycosyl group, is disclosed. Nitrogen oxides of such compounds are also included. These novel compounds have been found to be potent glycohydrolase inhibitors. Processes for preparing these novel compounds and methods for their use in the treatment of diabetes mellitus are also provided.

  本发明揭示了一种具有以下式子的化合物：##STR1## 其中n、m和p（可以相同也可以不同）是介于0和5之间的数字；q是介于0和10之间的数字；R.sub.1、R.sub.2、R.sub.3、R.sub.4和R.sub.5（可以相同也可以不同）是氢、羟基、卤素、具有1到6个碳的脂肪族、环烷或芳香族的O-脂肪族基团，或者是糖基团；而R.sub.4则是糖基团。这些化合物的氮氧化物也包括在内。这些新颖的化合物被发现是有效的糖苷酶抑制剂。本发明还提供了制备这些新颖化合物的方法以及在糖尿病治疗中使用它们的方法。
• Jespersen, Tina M.; Dong, Wenling; Sierks, Michael R., Angewandte Chemie, 1994, vol. 106, # 17, p. 1858 - 1860
  作者：Jespersen, Tina M.、Dong, Wenling、Sierks, Michael R.、Skrydstrup, Troels、Lundt, Inge、Bols, Mikael

  DOI：——

  日期：——
• Synthesis of isofagomine, a novel glycosidase inhibitor
  作者：Tina M. Jespersen、Mikael Bols、Michael R. Sierks、Troels Skrydstrup

  DOI：10.1016/s0040-4020(01)89351-0

  日期：1994.1

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