烯丙基-4,6-O-亚苄基-beta-D-吡喃葡萄糖苷 | 84276-56-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 中文名称: 烯丙基-4,6-O-亚苄基-beta-D-吡喃葡萄糖苷
• 中文别名: 烯丙基4,6-O-亚苄基-Β-D-吡喃葡萄糖苷
• 英文名称: allyl 4,6-O-benzylidene-β-D-glucopyranoside
• 英文别名: Allyl-4,6-O-benzylidene-beta-D-glucopyranoside；(4aR,6R,7R,8R,8aS)-2-phenyl-6-prop-2-enoxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxine-7,8-diol
• CAS: 84276-56-2
• 化学式: C₁₆H₂₀O₆
• 分子量: 308.331
• InChiKey: OMBCPFYQIULSGV-ANNNQLRWSA-N

物化性质

• 沸点：
  498.5±45.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  77.4
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  烯丙基-4,6-O-亚苄基-beta-D-吡喃葡萄糖苷 在 sodium hydride 、 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 、 paraffin 为溶剂， 反应 22.0h， 生成 2-丙烯-1-基 2,3-双-O-(苯基甲基)-BETA-D-吡喃葡萄糖苷
  参考文献：
  名称：

  Sugawara, Fumio; Nakayama, Haruhiko; Strobel, Gary A., Agricultural and Biological Chemistry, 1986, vol. 50, # 9, p. 2251 - 2260

  摘要：

  DOI：
• 作为产物：
  描述：

  D-葡萄糖 在 三氟甲磺酸 、 对甲苯磺酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.5h， 生成 烯丙基-4,6-O-亚苄基-beta-D-吡喃葡萄糖苷
  参考文献：
  名称：

  Synthesis of sulfur analogues of methyl and allyl kojibiosides and methyl isomaltoside and conformational analysis of the kojibiosides

  摘要：

  The synthesis of methyl and allyl 5'-thio-alpha-D-kojibiosides and methyl 5'-thio-alpha-D-isomaltoside is described. The phenylselenoglycoside and trichloroacetimidate of 2,3,4,6-tetra-O-acetyl-5-thioglucose have been employed as glycosyl donors to glycosylate glucopyranosyl accepters with 2-OH and 6-OH positions free. The disaccharides thus obtained are potential glucosidase inhibitors. The conformational preferences of allyl 5'-thiokojibioside (34) were studied by comparison of experimental NOE curves with the theoretical counterparts for the corresponding methyl glycoside 25, derived from a Boltzmann-averaged grid search using the program PIMM91. Very goad agreement of experimental NOE curves derived from selective NOE measurements with the theoretical curves is found. The data are consistent with the population of a global minimum structure Phi=-43, Psi-39 degrees) to the extent of 90%, and a second local minimum (Phi=-36, Psi=-173 degrees) to the extent of 6%. An X-ray crystal structure of 34 at 190 K (R=4.2%) indicates a conformation (Phi=-46, Psi=-23 degrees) that is similar to that of the global minimum.

  DOI：

  10.1016/s0957-4166(00)80386-9

文献信息

• The stereoselective conversion of 2-alkenyl alcohols to (R)- or (S)-alkane-1,2-diols using D-glucose as a chiral auxiliary
  作者：Gang Huang、Rawle I. Hollingsworth

  DOI：10.1016/s0040-4039(98)02472-1

  日期：1999.1

  followed by hydride reduction and removal of the saccharide fragment was used to prepare enantiomerically pure 1,2-dihydroxy alkanes. Diols of (R) or (S) configuration can be synthesized from (α)-glycosides or the (β) form respectively. Demercuration with chloride ion led to the insertion of a halo group adjacent to the new chiral center thus allowing for the possibility of further functionalization.

  将葡萄糖的2-羟基立体选择性地加到2-链烯基糖苷的巯基乙烯基上，然后将其氢化物还原并除去糖片段，用于制备对映体纯的1，2-二羟基烷烃。（R）或（S）构型的二元醇可以分别由（α）-糖苷或（β）形式合成。用氯离子脱汞导致在新的手性中心附近插入一个卤素基团，从而允许进一步官能化。
• Three Solvent-Free Catalytic Approaches to the Acetal Functionalization of Carbohydrates and Their Applicability to One-Pot Generation of Orthogonally Protected Building Blocks
  作者：Serena Traboni、Emiliano Bedini、Maddalena Giordano、Alfonso Iadonisi

  DOI：10.1002/adsc.201500745

  日期：2015.11.16

  alternative protocols were developed to carry out the selective installation of acetal groups on carbohydrates and polyols under mildly acidic, solvent-free conditions. One protocol is based on a diol/aldehyde condensation at room temperature, with an acetolysis process serving for the activation of the carbonyl component. A second approach is based on an orthoester-mediated activation of the carbonyl component

  开发了三种替代方案，以在弱酸性，无溶剂的条件下选择性地将缩醛基团安装在碳水化合物和多元醇上。一种方案是基于在室温下的二醇/醛缩合，其中乙酰解过程用于活化羰基组分。第二种方法是基于在高温下原酸酯介导的羰基组分的活化。第三方案相反是要求一种转缩醛化机制。这些方法的结合使得可以在非常简单的实验条件下，在空气中短时间内访问各种缩醛保护的构建基块。
• COMPOUND RETAINED IN TUMOR
  申请人：Toyo Suisan Kaisha, Ltd.

  公开号：EP2388264A1

  公开（公告）日：2011-11-23

  A novel compound which specifically resides in a tumor, a method for allowing it to reside in a tumor, and a method for detecting, diagnosing, and treating tumor with use thereof are provided. The present invention relates to a compound represented by chemical formula (I) wherein R is an anionic group binding to hydrogen, R1 is OH, OCOH, OCO(CH2)hCH3, or an acting group, h being an integer of 0 or more, R2 is H, OH, OCOH, OCO(CH2)iCH3, or an acting group, i being an integer of 0 or more, R3 is OH, SO3H, or an acting group, R4 is OH, SO3H, or an acting group, and R5 is OH, SO3H, or an acting group, at least one of R1, R2, R3, R4, and R5 containing an acting group, or pharmaceutically acceptable salts thereof.

  提供了一种新型化合物，该化合物特异地存在于肿瘤中，提供了一种使其在肿瘤中存在的方法，以及一种利用它进行肿瘤检测、诊断和治疗的方法。本发明涉及一种由化学式（I）表示的化合物，其中R是与氢结合的阴离子基团，R1是OH、OCOH、OCO（CH2）hCH3或作用基团，h为0或更多的整数，R2是H、OH、OCOH、OCO（CH2）iCH3或作用基团，i为0或更多的整数，R3是OH、SO3H或作用基团，R4是OH、SO3H或作用基团，R5是OH、SO3H或作用基团，R1、R2、R3、R4和R5中至少一个含有作用基团，或其药学上可接受的盐。
• Synthesis of some oligosaccharides containing the O-(2-acetamido-2-deoxy-β-d-glucopyranosyl)-(1→2)-O-α-d-mannopyranosyl unit. Potential substrates for UDP-GlcNAc: α-d-mannopyranosyl-(1→6)-N-acetyl-β-d-glucosaminyl-transferase (GnT-V)
  作者：Shaheer H. Khan、Saeed A. Abbas、Khushi L. Matta

  DOI：10.1016/0008-6215(89)85112-2

  日期：1989.10

  - d -glucopyranosyl-(1→2)-α- d -mannopyranosyl-(1→6)-β- d -glucopyranoside ( 31 ), and allyl O -(2-acetamido-2-deoxy-β- d -glucopyranosyl)-(1→2)- O -α- d -mannopyranosyl-(1→6)- O -β- d -glucopyranosyl-(1→4)-β- d - glucopyranoside ( 33 ). A common glycosyl donor, namely, 2- O -(2-acetamido-3,4,6-tri- O -acetyl-2-deoxy-β- d -glucopyranosyl)-3,4,6-tri- O -acetyl-α- d -mannopyranosyl bromide was employed

  摘要合成了以2-乙酰氨基-2-脱氧-β-d-吡喃葡萄糖基-（1→2）-α-d-甘露吡喃糖基序列为末端二糖单元的四种不同的低聚糖，即：4-硝基苯基O-（2-乙酰氨基-2-脱氧-β-d-吡喃葡萄糖基）-（1→2）-O-α-d-甘露吡喃糖基-（1→6）-β-d-甘露吡喃糖苷（27），4-硝基苯基O-（2-乙酰氨基-2-脱氧-β-d-吡喃葡萄糖基）-（1→2）-O-α-d-甘露吡喃糖基-（1→6）-β-d-吡喃葡糖苷（29），烯丙基O-（2-乙酰氨基- 2-脱氧-β-d-吡喃葡萄糖基-（1→2）-α-d-甘露吡喃糖基-（1→6）-β-d-吡喃葡萄糖苷（31）和烯丙基O-（2-乙酰氨基-2-脱氧- β-d-吡喃葡萄糖基）-（1→2）-O-α-d-甘露吡喃糖基-（1→6）-O-β-d-吡喃葡萄糖基-（1→4）-β-d-吡喃葡萄糖苷（33）。普通的糖基供体，即2-O-（2-乙酰氨基-3,4,6-三-O-
• COMPOUND HAVING TUMOR-RESIDENT PROPERTY
  申请人：OHTA Keisuke

  公开号：US20100202971A1

  公开（公告）日：2010-08-12

  The problem to be solved of the present invention is to provide a novel compound which specifically resides in a tumor, a method for allowing it to reside in a tumor, and a method for detecting, diagnosing, and treating tumor with use thereof. Means for solving the problem is a compound represented by chemical formula (I) wherein R is an anionic group binding to hydrogen, R 1 is OH, OCOH, OCO(CH 2 ) h CH 3 , or an acting group, h being an integer of 0 or more, R 2 is H, OH, OCOH, OCO(CH 2 ) i CH 3 , or an acting group, i being an integer of 0 or more, R 3 is OH, SO 3 H, or an acting group, R 4 is OH, SO 3 H, or an acting group, and R 5 is OH, SO 3 H, or an acting group, at least one of R 1 , R 2 , R 3 , R 4 , and R 5 containing an acting group, or pharmaceutically acceptable salts thereof.

  本发明要解决的问题是提供一种新型化合物，该化合物专门存在于肿瘤中，以及使其存在于肿瘤中的方法和使用其进行肿瘤检测、诊断和治疗的方法。解决问题的方法是提供一种由化学式（I）表示的化合物，其中R是与氢结合的负离子基团，R1是OH、OCOH、OCO（CH2）hCH3或作用基团，h是0或更多的整数，R2是H、OH、OCOH、OCO（CH2）iCH3或作用基团，i是0或更多的整数，R3是OH、SO3H或作用基团，R4是OH、SO3H或作用基团，R5是OH、SO3H或作用基团，其中R1、R2、R3、R4和R5中至少有一个含有作用基团，或其药学上可接受的盐。