3-O-allyl-D-glucopyranose | 91109-44-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-O-allyl-D-glucopyranose
• 英文别名: 3-O-allyl-D-glucose；(3R,4S,5R,6R)-6-(hydroxymethyl)-4-prop-2-enoxyoxane-2,3,5-triol
• CAS: 91109-44-3
• 化学式: C₉H₁₆O₆
• 分子量: 220.222
• InChiKey: VDMLDFBLAQXIKZ-NBTWYFBKSA-N

物化性质

• 沸点：
  430.0±45.0 °C(Predicted)
• 密度：
  1.37±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  99.4
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-O-allyl-D-glucopyranose 在 吡啶 、 zinc(II) chloride 作用下， 反应 12.17h， 生成 1,2-Di-O-acetyl-3-O-allyl-4,6-O-benzyliden-α-D-glucopyranose
  参考文献：
  名称：

  Paulsen, Hans; Wilkens, Roland; Reck, Folkert, Liebigs Annalen der Chemie, 1992, # 12, p. 1303 - 1314

  摘要：

  DOI：
• 作为产物：
  描述：

  D-glucose 在 IRa-1 20 (H⁺) 、 硫酸 、 水 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 3-O-allyl-D-glucopyranose
  参考文献：
  名称：

  Design and synthesis of functionalized glycomers as non-peptidic ligands for SH2 binding and as inhibitors of A-431 human epidermoid and HT-29 colon carcinoma cell lines

  摘要：

  A set of O-subsiitutsd aryl beta-D-glucopyranosides were prepared and found to have inhibitory activity on the growth of two carcinona cell lines. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00022-6

文献信息

• Ring-selective synthesis of O-heterocycles from acyclic 3-O-allyl-monosaccharides via intramolecular nitrone–alkene cycloaddition
  作者：Tony K.M Shing、Yong-Li Zhong

  DOI：10.1016/s0040-4020(00)01138-8

  日期：2001.2

  Intramolecular 1,3-dipolar cycloadditions of nitrones formed from 3-O-allyl-d-glucose and d-altrose (both with threo-configuration at C-2,3) afford oxepanes selectively whereas the same reactions of nitrones derived from 3-O-allyl-d-allose and d-mannose (both with erythro-configuration at C-2,3) give tetrahydropyrans selectively.

  由3 - O-烯丙基-d-葡萄糖和d-altrose（均在C-2,3处具有苏-构型）形成的硝酮的分子内1,3-偶极环加成反应可选择性地提供氧杂环丁烷，而衍生自3-的硝酮的相同反应O-烯丙基-d-阿洛糖和d-甘露糖（在C-2,3处均具有赤型构型）选择性地产生四氢吡喃。
• Studies on synthesis of 3-O-alkyl-D-glucose and 3-O-alkyl-D-allose derivatives and their biological activities.
  作者：TETSURO IKEKAWA、KAZUHIKO IRINODA、KOICHI SAZE、TATSUHIKO KATORI、HIDEAKI MATSUDA、MASANORI OHKAWA、MARTIN KOSIK

  DOI：10.1248/cpb.35.2894

  日期：——

  Twenty two 3-Ο-alkyl derivatives of D-glucose and D-allose, four 3-Ο-alkenyl derivatives of D-glucose having an end methylene group, and four 3-Ο-ω-hydroxyalkyl- or -methoxyalkyl derivatives of D-glucose were synthesized. Their cytotoxicity in vitro against the cultured leukemia L-5178Y cell line, antimicrobial activity and plant growth-inhibitory effect were determined.

  合成了二十二种D-葡萄糖和D-阿洛糖的3-O-烷基衍生物、四种末端甲撑基的D-葡萄糖3-O-烯基衍生物和四种D-葡萄糖的3-O-ω-羟基烷基或-甲氧基烷基衍生物。测定了它们对体外培养的白血病L-5178Y细胞的细胞毒性、抗菌活性和植物生长抑制作用。
• Silyl-assisted 1,2-cis-α-glucosylation for the synthesis of a triglucoside moiety in high-mannose-type oligosaccharides
  作者：Kiichiro Totani、Yuki Shinoda、Masaaki Shiba、Shogo Iwamoto、Akira Koizumi、Yuji Matsuzaki、Makoto Hirano

  DOI：10.1039/c5ra16659d

  日期：——

  We developed a new 1,2-cis-α-glucosylation reaction, mediated by enhancing the α-favoured transition state via an electron-donating form the TBS group.

  我们开发了一种新的1,2-cis-α-葡萄糖基化反应，通过增强α-偏向过渡态通过从TBS基团中提供电子的方式来介导。
• [EN] SYNTHETIC OLIGOSACCHARIDES FOR P. AERUGINOSA VACCINE<br/>[FR] OLIGOSACCHARIDES DE SYNTHÈSE POUR VACCIN CONTRE P. AERUGINOSA
  申请人：SYNGLYCO PHARMACEUTICALS INC

  公开号：WO2015002954A1

  公开（公告）日：2015-01-08

  The present invention provides synthetic Pseudomonas aeruginosa lipooligosaccharide (LOS)-based oligosaccharides and conjugates containing various P. aeruginosa serotype-specific oligosaccharide antigens or various core P. aeruginosa oligosaccharide structures or motifs. The invention further provides P. aeruginosa LOS-based immunogenic and immunoprotective compositions and antibodies derived therefrom for diagnosing, treating, and preventing infections caused by P. aeruginosa.

  本发明提供了合成的假单胞菌脂寡糖（LOS）基寡糖和含有不同假单胞菌血清型特异性寡糖抗原或不同核心假单胞菌寡糖结构或基序的共轭物。该发明还提供了基于假单胞菌LOS的免疫原和免疫保护组合物，以及由此衍生的抗体，用于诊断、治疗和预防由假单胞菌引起的感染。
• Preparation of a glycosyl donor suitable for synthesis of glycoprotein “core” oligosaccharides
  作者：Charng-Ming Liu、Christopher D. Warren、Roger W. Jeanloz

  DOI：10.1016/0008-6215(85)85203-4

  日期：1985.2

  2-O-Acetyl-3-O-allyl-4-O-benzyl-6-O-tert-butyldiphenylsilyl-D-gluc opyranosyl chloride (14), a glycosyl donor suitable for synthesis of oligosaccharides corresponding to the N-glycoprotein saccharide "core", was synthesized by an efficient, six-stage route from 3,4,6-tri-O-acetyl-1,2-O-[1-(exo-ethoxy)ethylidene)-alpha-D-glucopyranos e. Silver triflate-promoted coupling of 14 with benzyl 2-acetamido-3

  2-O-乙酰基-3-O-烯丙基-4-O-苄基-6-O-叔丁基二苯基甲硅烷基-D-葡萄糖吡喃糖基氯（14），一种适合合成对应于N-糖蛋白糖的寡糖的糖基供体“核心”是由3,4,6-三-O-乙酰基-1,2-O- [1-（外-乙氧基）亚乙基）-α-D-吡喃葡萄糖通过高效的六步路线合成的。由三氟甲磺酸银促进的14与苄基2-乙酰氨基-3,6-二-O-苄基-2-脱氧-α-D-吡喃葡萄糖苷的偶联产生了受保护的与β-D-（1 ---- 4）连接的二糖收率38％，但也发生了主要的副反应。当在偶联反应之前将叔丁基二苯基甲硅烷基从14定量除去后再取代时，糖苷化的产率增加到55％，并且避免了主要副产物。