1,3,4,6-tetra-O-acetyl-2-deoxy-2-(4-methoxybenzylidene)amino-D-α-glucopyranose | 7597-81-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1,3,4,6-tetra-O-acetyl-2-deoxy-2-(4-methoxybenzylidene)amino-D-α-glucopyranose
• 英文别名: 1,3,4,6-tetra-O-acetyl-2-(4'-methoxybenzylidene)amino-2-desoxy-α-D-galactopyranose；[(3S,5S,6S)-3,4,6-triacetyloxy-5-[(4-methoxyphenyl)methylideneamino]oxan-2-yl]methyl acetate；1,3,4,6-Tetra-O-acetyl-2-desoxy-2-[4-methoxy-benzylidenamino]-β-D-glucopyranose；(2S,3R,4R,5S,6R)-6-(acetoxymethyl)-3-((E)-(4-methoxybenzylidene)amino)tetrahydro-2Hpyran-2,4,5-triyl triacetate；6-(acetoxymethyl)-3-(((E)-4-methoxybenzylidene)amino)tetrahydro-2H-pyran-2,4,5-triyltriacetate；1,3,4,6-Tetra-O-acetyl-2-desoxy-2-<4-methoxy-benzylidenamino>-β-D-glucopyranose；1,3,4,6-Tetra-O-acetyl-2-desoxy-2-(4-methoxy-benzylidenamino)-β-D-glucopyranose
• CAS: 7597-81-1；34948-61-3；55628-19-8；74554-00-0；103382-86-1；114297-26-6
• 化学式: C₂₂H₂₇NO₁₀
• 分子量: 465.457
• InChiKey: BPVDJXUNJWJXMH-QOTAKQIMSA-N

物化性质

• 熔点：
  181-183°C
• 沸点：
  559.3±50.0 °C(Predicted)
• 密度：
  1.30±0.1 g/cm3(Predicted)
• 溶解度：
  可溶于氯仿、乙酸乙酯、甲醇

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  33.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  136.02
• 氢给体数：
  0.0
• 氢受体数：
  11.0

安全信息

• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

反应信息

• 作为反应物：
  描述：

  1,3,4,6-tetra-O-acetyl-2-deoxy-2-(4-methoxybenzylidene)amino-D-α-glucopyranose 在 盐酸 作用下， 以 丙酮 为溶剂， 以82%的产率得到1,3,4,6-四-O-乙酰基-2-氨基-2-脱氧-Β-D-葡萄糖盐酸盐
  参考文献：
  名称：

  2-氨基-2-脱氧-d-葡萄糖的N-烷氧羰基衍生物在糖基化反应中作为供体的用途

  摘要：

  1,3,4,6-四-O-乙酰基-2-烷氧基羰基氨基-2-脱氧-β-D-glu复制糖和3,4,6-三-O-乙酰基-2-烷氧基羰基氨基-2-脱氧-α在与模型醇的糖基化反应中，已将-D-吡喃葡萄糖烷基溴用作供体。β-糖苷以高收率和高度的1，2-反式立体选择性获得。恶唑烷酮是一些吡喃葡萄糖基溴化物与低反应性醇反应形成的主要产物，但所有产物的形成都可以通过烷氧基羰基氨基的强烈参与来解释。

  DOI：

  10.1016/0008-6215(90)84077-8
• 作为产物：
  描述：

  2-氨基-2-脱氧葡萄糖盐酸盐 在 吡啶 、 sodium hydroxide 作用下， 生成 1,3,4,6-tetra-O-acetyl-2-deoxy-2-(4-methoxybenzylidene)amino-D-α-glucopyranose
  参考文献：
  名称：

  SYNTHESIS OF 4-ACYL-1H-1,2,3-TRIAZOLIC NUCLEOSIDES

  摘要：

  Two simple regiospecific methodologies based on triazolic ring construction in the course of synthesis were applied for the synthesis of 1,2,3-triazolic nucleoside analogues. The cycloaddition reactions between diazomalonaldehyde and appropriate glycosylamine derivatives were rather effective, producing the desired nucleosides 11, 17 and 24. Diazotization of enamines 21a and 21b led to the corresponding triazolic ribonucleoside derivatives 22a and 22b, in good yields. Deprotection reaction of 22a, 22b and 24 was easily achieved by Lewis acid catalysis, producing the corresponding ribonucleosides 23a, 23b and 25.

  DOI：

  10.1081/ncn-100105247

文献信息

• [EN] SELECTIVE GLYCOSIDASE INHIBITORS AND USES THEREOF<br/>[FR] INHIBITEURS SÉLECTIFS DE LA GLYCOSIDASE ET UTILISATIONS DE CEUX-CI
  申请人：ALECTOS THERAPEUTICS INC

  公开号：WO2012064680A1

  公开（公告）日：2012-05-18

  The invention is directed to compounds for selectively inhibiting glycosidases, uses of the compounds and pharmaceutical compositions including the compounds, and methods of treating diseases and disorders related to deficiency or overexpression of O-GlcNAcase, and/or accumulation or deficiency of O-GlcNAc.

  该发明涉及用于选择性抑制糖苷酶的化合物，包括这些化合物的用途和药物组合物，以及治疗与O-GlcNAcase的缺乏或过度表达，以及O-GlcNAc的积累或缺乏相关的疾病和紊乱的方法。
• [EN] PYRANO[3,2-D]THIAZOL DERIVATIVES AND USES THEREOF AS SELECTIVE GLYCOSIDASE INHIBITORS<br/>[FR] DÉRIVÉS DE PYRANO[3,2-D]THIAZOLE ET LEURS UTILISATIONS EN TANT QU'INHIBITEURS SÉLECTIFS DES GLYCOSIDASES
  申请人：ALECTOS THERAPEUTICS INC

  公开号：WO2012062157A1

  公开（公告）日：2012-05-18

  Pyrano[3,2-d]thiazol derivatives of formula (I) for selectively inhibiting glycosidases, uses of the compounds and pharmaceutical compositions including the compounds are disclosed. Methods of treating diseases and disorders related to deficiency or overexpression of O-GlcNAcase, accumulation or deficiency of O-GlcNAc are also provided.

  公开了用于选择性抑制糖苷酶的式(I)的Pyrano[3,2-d]噻唑衍生物，以及包括这些化合物的药用组合物的用途。还提供了治疗与O-GlcNA酶缺乏或过度表达、O-GlcNAc积累或缺乏相关的疾病和紊乱的方法。
• [EN] SELECTIVE GLYCOSIDASE INHIBITORS AND USES THEREOF<br/>[FR] INHIBITEURS SÉLECTIFS DE LA GLYCOSIDASE ET SES UTILISATIONS
  申请人：ALECTOS THERAPEUTICS INC

  公开号：WO2012061972A1

  公开（公告）日：2012-05-18

  The invention is directed to compounds for selectively inhibiting glycosidases, uses of the compounds and pharmaceutical compositions including the compounds, and methods of treating diseases and disorders related to deficiency or overexpression of O-GlcNAcase, and/or accumulation or deficiency of O-GlcNAc.

  该发明涉及用于选择性抑制糖苷酶的化合物，包括该化合物的用途和药物组合物，以及治疗与O-GlcNAcase的缺乏或过度表达，以及O-GlcNAc的积累或缺乏相关的疾病和紊乱的方法。
• HF-Induced Intramolecular <i>C</i>-Arylation and <i>C</i>-Alkylation/Fluorination of 2-Aminoglycopyranoses
  作者：Nicolas Probst、Amélie Martin、Jérôme Désiré、Agnès Mingot、Jérôme Marrot、Yves Blériot、Sébastien Thibaudeau

  DOI：10.1021/acs.orglett.7b00003

  日期：2017.3.3

  Internal C-aryl and C-alkyl glycosides derived from 2-aminoglycopyranoses have been synthesized, exploiting a HF-mediated stereoselective intramolecular glycosylation. These conditions are compatible with acetate protecting groups and allow introduction of aromatics with various electronic distributions at the anomeric position. This strategy also provides straightforward entry to original fluorinated

  利用HF介导的立体选择性分子内糖基化，已经合成了衍生自2-氨基糖基葡萄糖的内部C-芳基和C-烷基糖苷。这些条件与乙酸酯保护基相容，并允许引入在端基异构位置具有各种电子分布的芳族化合物。该策略还通过串联内部C-糖基化/氟化反应（从2- N-烯丙基/炔丙基糖吡喃糖开始），直接进入原始的氟化糖-氮杂二环杂化物。所有环化均以1,2-顺式立体控制的方式进行。
• The use of N-alkoxycarbonyl derivatives of 2-amino-2-deoxy-d-glucose as donors in glycosylation reactions
  作者：Paul Boullanger、Martine Jouineau、Boufelja Bouammali、Dominique Lafont、Gérard Descotes

  DOI：10.1016/0008-6215(90)84077-8

  日期：1990.7

  6-tri-O-acetyl-2-alkoxycarbonylamino-2-deoxy-alpha-D-glucopyra nosyl bromides have been used as donors in glycosylation reactions with model alcohols. beta-Glycosides were obtained in good yields and with a high degree of 1,2-trans stereoselectivity. An oxazolidinone was formed as the main product from the reaction of some of the glucopyranosyl bromides with alcohols of low reactivity, but the formation

  1,3,4,6-四-O-乙酰基-2-烷氧基羰基氨基-2-脱氧-β-D-glu复制糖和3,4,6-三-O-乙酰基-2-烷氧基羰基氨基-2-脱氧-α在与模型醇的糖基化反应中，已将-D-吡喃葡萄糖烷基溴用作供体。β-糖苷以高收率和高度的1，2-反式立体选择性获得。恶唑烷酮是一些吡喃葡萄糖基溴化物与低反应性醇反应形成的主要产物，但所有产物的形成都可以通过烷氧基羰基氨基的强烈参与来解释。