D-吡喃葡萄糖 | 35810-56-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: D-吡喃葡萄糖
• 英文名称: α-L-mannopyranose
• 英文别名: β-L-mannopyranose；α-D-mannose；α-L-mannose；L-(-)-mannose；L-Mannose；alpha-L-mannopyranose；(2R,3R,4R,5R,6S)-6-(hydroxymethyl)oxane-2,3,4,5-tetrol
• CAS: 35810-56-1
• 化学式: C₆H₁₂O₆
• 分子量: 180.158
• InChiKey: WQZGKKKJIJFFOK-HGVZOGFYSA-N

物化性质

• 沸点：
  410.8±45.0 °C(Predicted)
• 密度：
  1.732±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2.6
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  110
• 氢给体数：
  5
• 氢受体数：
  6

安全信息

• 海关编码：
  2924199090

反应信息

• 作为反应物：
  描述：

  D-吡喃葡萄糖 在 吡啶 、 乙酰溴 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 反应 46.0h， 生成 2,3,6-Tri-O-benzoyl-4-O-chloroacetyl-α-L-mannopyranosyl bromide
  参考文献：
  名称：

  Achiral Cyclodextrin Analogues

  摘要：

  AbstractThe synthesis of a new family of cyclodextrin (CD) analogues is described. This family consists of novel cyclic oligosaccharides built from monosaccharides that possess the same relative but opposite absolute (D‐ and L‐) configurations. The alternation of such D‐ and L‐ residues—specifically, D‐ and L‐rhamnose or D‐ and L‐mannose—in a macrocyclic structure results in Sn‐type symmetry and, consequently, optical inactivity. The synthesis of these cyclic oligosaccharides was achieved by an economical polycondensation/cycloglycosylation approach that relies on an appropriately‐derivatized disac‐charide monomer and that avoids the time‐consuming, and often low‐yielding, stepwise growth of long linear oligosaccharide precursors. In the cases reported, the key precursors are the disaccharide monomers 1‐RR and 1‐MM, which bear both a glycosyl donor (cyanoethylidene function) and a glycosyl acceptor (trity‐loxy group). These compounds are able to undergo Tr+‐catalyzed polycondensation which, under appropriate dilution conditions, can be terminated by cycloglycosyl‐ation. Thus, compound 1‐RR was converted into a range of protected cyclic rhamnooligosaccharides 15–19 in 64% overall yield. All these products, including the unique cyclic dodeca‐ and tetradecasaccharides 18 and 19, have been isolated by preparative HPLC. Unexpectedly, treatment of the manno analogue of the disaccharide 1‐RR (compound 1‐MM) under the same conditions produced only the cyclic hexasaccharide 28 and numerous apparently linear oligomers. Removal of the protecting groups from 16–19 afforded the free cyclic oligosaccharides 21–24, which exhibited the predicted zero optical rotation and very simple NMR spectra, indicating highly symmetrical structures. X‐ray crystallography reveals that in the solid state the cyclooctaoside 21 possesses a C2 symmetric structure, on account of a slight deformation of its cylindrical shape. The channel‐type crystal packing of molecules of 21 forms nanotubes with an internal diameter of around 1 nm. Conversely, the cyclic hexasaccharide 29 possesses a Ci symmetric solid‐state structure and its molecules pack to form a parquet‐like superstructure.

  DOI：

  10.1002/chem.19970030818
• 作为产物：
  描述：

  L-mannose phenylhydrazone 、 水 、 苯甲醛 、 苯甲酸 在 苯甲醛苯腙 、 氯仿 、 乙醇 、 水 作用下， 以 乙醇 为溶剂， 反应 27.0h， 以to give α-L-mannopyranose, m.p. 125°-126°, [α]D -26.9°→-14.4° (24 hr., c 2.0, water)的产率得到D-吡喃葡萄糖
  参考文献：
  名称：

  L-Sucrose and process for producing same

  摘要：

  L-蔗糖或β-L-果糖呋喃基-α-L-葡萄糖苷（I），是天然存在的D-蔗糖的对映体，不会出现在自然界中，已被合成，并被发现具有甜味。 L-蔗糖不太可能像D-蔗糖那样被代谢。 在制备L-蔗糖的首选工艺中，关键步骤是将2,3,4,6-四-O-苯甲酰-α-L-葡萄糖苷氯化物（II）与1,3,4,6-四-O-苯甲酰-L-果糖呋喃糖（III）缩合。化合物II是通过2,3,4,6-四-O-苯甲酰-α-L-葡萄糖苷制备的，而L-葡萄糖则通过硝基甲烷合成法从L-阿拉伯糖制备而来。化合物III是通过Jones试剂氧化1,3,4,6-四-O-苯甲酰-L-甘露醇获得的，而1,3,4,6-四-O-苯甲酰-L-甘露醇则是由L-甘露糖制备而来。 II和III的缩合产物通过催化脱苯甲基可产生L-蔗糖。

  公开号：

  US04207413A1

文献信息

• Pharmaceutically active compounds and their use
  申请人：Laboratorio CHile S.A.

  公开号：US05747462A1

  公开（公告）日：1998-05-05

  The present invention relates to the area of pharmacology; its objective is to solve the technical problem of inflammation, pain, pruritus and local hyperthermia in human beings and animal species. The composition and the subcompositions thereof are obtained from plants of the family Cactaceae, the main methodological steps being a set of processes: production, purification, physicochemical quantification, biotherapeutic evaluation, biopharmaceutical formulation and molecular identification. From the molecular identification a set of molecules is recognized, comprising carbohydrates and an aromatic amine, the general formulae of which are: C.sub.5 H.sub.10 O.sub.5 (RIBOSE), C.sub.6 H.sub.12 O.sub.5 (FUCOSE), C.sub.6 H.sub.12 O.sub.6 (GALACTOSE; MANNOSE; GLUCOSE), C.sub.8 H.sub.11 O.sub.2 N (1-HYDROXY-1-(4-HYDROXYPHENYL)-2-AMINOETHANE), C.sub.10 H.sub.18 O.sub.9 (RIBOFURANOSYLRIBOSE).

  本发明涉及药理学领域，其目的是解决人类和动物物种中的炎症、疼痛、瘙痒和局部高热问题。该组合物及其亚组分是从仙人掌科植物中获得的，其主要方法步骤包括一系列过程：生产、纯化、物理化学定量、生物治疗评估、生物制药配方和分子鉴定。从分子鉴定中识别出一组分子，包括碳水化合物和芳香胺，其通用式为：C.sub.5 H.sub.10 O.sub.5（核糖）、C.sub.6 H.sub.12 O.sub.5（岩藻糖）、C.sub.6 H.sub.12 O.sub.6（半乳糖；甘露糖；葡萄糖）、C.sub.8 H.sub.11 O.sub.2 N（1-羟基-1-(4-羟基苯基)-2-氨基乙烷）、C.sub.10 H.sub.18 O.sub.9（核糖呋喃糖核糖）。
• Compositions containing carbohydrates obtained from plants of the family cactacea
  申请人：LABORATORIO CHILE S.A.

  公开号：EP0706797A2

  公开（公告）日：1996-04-17

  Therapeutic formulations for the treatment of inflammation, pain, pruritis and local hyperthermia are based on carbohydrate/amine compositions obtained from plants of the family Cactaceae.

  用于治疗炎症、疼痛、瘙痒症和局部高热的治疗配方以从仙人掌科植物中提取的碳水化合物/胺成分为基础。
• Carbohydrate-glycolipid conjugate vaccines
  申请人：Max-Planck-Gesellschaft zur Förderung der Wissenschaften e.V.

  公开号：US10588962B2

  公开（公告）日：2020-03-17

  The present invention relates to the field of synthesizing and biologically evaluating of a novel class of carbohydrate-based vaccines. The new vaccines consist of a multi-modular structure which allows applying the vaccine to a whole variety of pathogenes. This method allows preparing vaccines against all pathogens expressing immunogenic carbohydrate antigens. As conjugation of antigenic carbohydrates to proteins is not required the conjugate vaccine is particularly heat stable. No refrigeration is required, a major drawback of protein-based vaccines.

  本发明涉及一类基于碳水化合物的新型疫苗的合成和生物评估领域。这种新型疫苗由多模块结构组成，可将疫苗应用于各种病原体。这种方法可以制备出针对所有表达免疫原性碳水化合物抗原的病原体的疫苗。由于不需要将抗原碳水化合物与蛋白质共轭，共轭疫苗的热稳定性特别好。无需冷藏，这是基于蛋白质的疫苗的一个主要缺点。
• Syntheses of l-glucosamine donors for 1,2-trans-glycosylation reactions
  作者：Dominique Lafont、Paul Boullanger

  DOI：10.1016/j.tetasy.2006.12.011

  日期：2006.12

  Two new L-glucosarnine donors, that is pent-4-enyl 3,4,6-tri-O-acetyl-2-allyloxycarbonylamino-2-deoxy-beta-L-glucopyranoside 16 and ethyl 3,4,6-tri-O-acetyl-2-allyloxycarbonylamino-2-deoxy-l-thio-beta-L-glucopyranoside 21 were prepared in 12 steps from L-arabinose. The reaction pathway uses 3,4,6-tri-O-acetyl-L-glucal 5, and then 3,4,6-tri-O-acetyl-2-deoxy-2-iodO-alpha-L-mannopyranosyl azide 8 as intermediates. The latter, together with donors 16 and 21, were used for preparing L-glucosamine neoglycolipids. (c) 2007 Elsevier Ltd. All rights reserved.
• Indoloditerpenes from a Marine-Derived Fungal Strain of <i>Dichotomomyces cejpii</i> with Antagonistic Activity at GPR18 and Cannabinoid Receptors
  作者：Henrik Harms、Viktor Rempel、Stefan Kehraus、Marcel Kaiser、Peter Hufendiek、Christa E. Müller、Gabriele M. König

  DOI：10.1021/np400850g

  日期：2014.3.28

  A marine-derived strain of Dichotomomyces cejpii produces the new compounds emindole SB beta-mannoside (1) and 27-O-methylasporyzin C (2), as well as the known indoloditerpenes JBIR-03 (3) and emindole SB (4). Indo le derivative 1 was found to be a CB2 antagonist, while 2 was identified as the first selective GPR18 antagonist with an indole structure. Compound 4 was found to be a nonselective CB1/CB2 antagonist. The new natural indole derivatives may serve as lead structures for the development of GPR18- and CB receptor-blocking drugs.

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