4,6-O-benzylidene-α-D-glucopyranose | 113566-67-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: 4,6-O-benzylidene-α-D-glucopyranose
• 英文别名: 4,6-O-Benzylidene-α-D-glucose；4,6-O-benzylidene-D-glucopyranose；(2R,4aR,6S,7R,8R,8aS)-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxine-6,7,8-triol
• CAS: 113566-67-9
• 化学式: C₁₃H₁₆O₆
• 分子量: 268.266
• InChiKey: FOLRUCXBTYDAQK-WXCVZDNMSA-N

物化性质

• 熔点：
  181-183 °C
• 沸点：
  483.4±45.0 °C(Predicted)
• 密度：
  1.436±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  88.4
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4,6-O-benzylidene-α-D-glucopyranose 在 sodium periodate 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 0.75h， 以63%的产率得到2,4-O-Benzylidene-3-formyl-D-erythrose
  参考文献：
  名称：

  Friedrich, Klaus; Fraser-Reid, Bert, Journal of Carbohydrate Chemistry, 1994, vol. 13, # 4, p. 631 - 640

  摘要：

  DOI：
• 作为产物：
  描述：

  N,O-dimethyl-N-(4,6-O-benzylidene-β-D-glucopyranosyl)hydroxylamine 在 N-氯代丁二酰亚胺 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 1.0h， 生成 4,6-O-benzylidene-α-D-glucopyranose 、 4,6-O-benzylidene-β-D-glucopyranose
  参考文献：
  名称：

  Use of N,O-Dimethylhydroxylamine As an Anomeric Protecting Group in Carbohydrate Synthesis

  摘要：

  The N,O-dimethyloxyamine-N-glycosides are introduced as anomerically protected building blocks for carbohydrate synthesis. These N-glycosides are stable to a variety of protecting group manipulations including acylation, alkylation, silylation, and acetal formation. The alkoxyamine-N-glycosides can be cleaved selectively with N-chlorosuccinimide to give the desired hemiacetals in excellent yield. Furthermore, these N-glycosides are stable to the activation conditions required for glycosylation using thioglycoside and trichloroacetimidate glycosyl donors suggesting N,O-dialkoxyamine-N-glycosides will be useful for complex oligosaccharide synthesis.

  DOI：

  10.1021/jo102372m

文献信息

• 3,5-DIAMINO-6-CHLORO-N-(N-(4-PHENYLBUTYL)CARBAMIMIDOYL) PYRAZINE-2- CARBOXAMIDE COMPOUNDS
  申请人：Parion Sciences, Inc.

  公开号：US20140170244A1

  公开（公告）日：2014-06-19

  The present invention relates compounds of the formula: or pharmaceutically acceptable salts thereof, useful as sodium channel blockers, as well as compositions containing the same, processes for the preparation of the same, and therapeutic methods of use therefore in promoting hydration of mucosal surfaces and the treatment of diseases including cystic fibrosis, chronic obstructive pulmonary disease, asthma, bronchiectasis, acute and chronic bronchitis, emphysema, and pneumonia.

  本发明涉及以下式的化合物： 或其药用可接受的盐，用作钠通道阻滞剂，以及含有相同化合物的组合物，制备相同化合物的方法，以及在促进粘膜表面水合和治疗包括囊性纤维化、慢性阻塞性肺病、哮喘、支气管扩张、急性和慢性支气管炎、肺气肿和肺炎等疾病的治疗方法。
• 4,6-O-Benzylidene-d-glucopyranose and its sodium salt: new data on their preparation and properties
  作者：Pier Luigi Barili、Giancarlo Berti、Giorgio Catelani、Carlo Cini、Felicia D'Andrea、Ettore Mastrorilli

  DOI：10.1016/0008-6215(95)00227-8

  日期：1995.11

  An improved method for the preparation of 4,6-O-benzylidene-D-glucopyranose (BG), and new or correlated data on its 1H and 13C NMR spectra, specific rotations, and tautomeric equilibria, and on those of its anomeric sodium salt (BGNa), are reported. Evidence is presented in favour of the hypothesis that crystalline BGNa exists entirely in its beta-anomeric form and that it can be useful in the access

  一种改进的制备4,6-O-亚苄基-D-吡喃葡萄糖（BG）的方法，以及有关其1H和13C NMR光谱，比旋光和互变异构体以及其端基异构钠盐的新数据或相关数据（BGNa）。提出的证据支持以下假设：结晶BGNa完全以其β-异头物形式存在，并且在严格异质条件下与强亲电试剂反应中可用于获得β-葡萄糖苷。
• Acetolysis of a 2,4-O-benzylidene-l-ribo-hex-5-enitol derivative
  作者：János Kuszmann、Benjámin Podányi

  DOI：10.1016/0008-6215(94)80036-7

  日期：1994.5

  Abstract Acetolysis of ( Z )-1,3-di- O -acetyl-2,4- O -benzylidene-5,6-dideoxy-6- C -(2,4-dichlorophenyl)- l - ribo -hex-5-enitol afforded, besides 2- C -[( S )-acetoxy(2,4-dichlorophenyl)methyl]-3,4,6-tri- O -acetyl-2-deoxy-β- d - allo - and - gluco -hexopyranosylbenzene, ( E )-1,2,3,4-tetra- O -acetyl-5,6-dideoxy-6- C -(2,4-dichlorophenyl)- d - lyxo - and - l - ribo -hex-5-enitol as main products. The

  摘要（Z）-1,3-二-O-乙酰基-2,4-O-亚苄基-5,6-二脱氧-6-C-（2,4-二氯苯基）-1-核糖-hex-5的乙解-2-烯醇，除了2-C-[（S）-乙酰氧基（2,4-二氯苯基）甲基] -3,4,6-三-O-乙酰基-2-脱氧-β-d-异位-和-葡萄糖-己基吡喃糖基苯，（E）-1,2,3,4-四-O-乙酰基-5,6-二脱氧-6- C-（2,4-二氯苯基）-d-lyxo-和-l-ribo -hex -5-烯醇为主要产品。该反应的速率以及产物的比例取决于C-3的手性。通过乙酰解相应的1-赤-戊-4-烯醇衍生物来证实这一点。
• Glycorandomization and production of novel vancomycin analogs
  申请人：Wisconsin Alumni Research Foundation

  公开号：US20040259228A1

  公开（公告）日：2004-12-23

  The present invention provides combinatorial methods for rapidly generating a diverse library of glycorandomized structures, comprising incubating one or more aglycons and a pool of NDP-sugars in the presence of a glycosyltransferase. The glycosyltransferase may be one that is associated with or involved in production of natural secondary metabolites, or one which is putatively associated with or involved in production of natural secondary metabolites. The glycosyltransferase may show significant flexibility with respect to its NDP-sugar donors and/or its aglycons. NDP-sugar donors may be commercially available, or may be produced by utilizing mutant or wild type nucleotidyltransferases significant flexibility with respect to their substrates.

  本发明提供了快速生成多种糖随机化结构库的组合方法，包括在糖基转移酶存在下培养一种或多种琼脂糖和NDP-糖池。糖基转移酶可以是与天然次生代谢物的生产有关或参与生产的糖基转移酶，也可以是推测与天然次生代谢物的生产有关或参与生产的糖基转移酶。糖基转移酶在其 NDP-糖供体和/或其糖醛酸方面可以表现出很大的灵活性。NDP 糖供体可以从市场上买到，也可以通过利用突变型或野生型核苷酸转移酶对底物的极大灵活性来生产。
• Glycorandomization and Production of Novel Novobiocin Analogs
  申请人：Thorson Jon

  公开号：US20120264924A1

  公开（公告）日：2012-10-18

  The present invention provides glycorandomized structures and combinatorial methods for rapidly generating a diverse library of glycorandomized structures, comprising incubating one or more aglycons and a pool of NDP-sugars in the presence of a glycosyltransferase. The glycosyltransferase may be one that is associated with or involved in production of natural secondary metabolites, or one which is putatively associated with or involved in production of natural secondary metabolites. The glycosyltransferase may show significant flexibility with respect to its NDP-sugar donors and/or its aglycons. NDP-sugar donors may be commercially available, or may be produced by utilizing mutant or wild type nucleotidyltransferases significant flexibility with respect to their substrates.