3,4,6-tri-O-acetyl-1,2-anhydro-β-D-mannopyranose | 161016-87-1

• 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: 3,4,6-tri-O-acetyl-1,2-anhydro-β-D-mannopyranose
• 英文别名: 1,2-anhydro-3,4,6-tri-O-aceyl-β-D-mannopyranose；[(1R,3R,4R,5S,6S)-4,5-diacetyloxy-2,7-dioxabicyclo[4.1.0]heptan-3-yl]methyl acetate
• CAS: 161016-87-1
• 化学式: C₁₂H₁₆O₈
• 分子量: 288.254
• InChiKey: WOMJWRCQBLDWOJ-GCHJQGSQSA-N

物化性质

• 沸点：
  364.4±42.0 °C(predicted)
• 密度：
  1.34±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  101
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  3,4,6-tri-O-acetyl-1,2-anhydro-β-D-mannopyranose 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 生成 Acetic acid (2R,3S,4R,5S,6R)-2-acetoxymethyl-6-fluoro-4,5-dihydroxy-tetrahydro-pyran-3-yl ester
  参考文献：
  名称：

  A stereoselective and preparative entry to 1,2-anhydrosugars through oxidation of glycals with perfluoro-cis-2,3-dialkyloxaziridines

  摘要：

  全氟顺式-2,3-二烷氧杂环丁烯1能够直接对糖苷2进行环氧化反应，清晰地产生相应的1,2-脱水糖3，并具有中等到完全的二氟选择性；还报告了这些糖苷转化为糖苷氟化物和脂类共轭物的研究。

  DOI：

  10.1039/c39950000901
• 作为产物：
  描述：

  乙酰化葡萄烯糖 在 Oxone 、 四丁基硫酸氢铵 、 碳酸氢钠 作用下， 以 二氯甲烷 、 水 、 丙酮 为溶剂， 生成 Brigl's anhydride 、 3,4,6-tri-O-acetyl-1,2-anhydro-β-D-mannopyranose
  参考文献：
  名称：

  β-Configured clickable [¹⁸F]FDGs as novel ¹⁸F-fluoroglycosylation tools for PET

  摘要：

  我们开发了一种用于PET成像的化学选择性¹⁸F-氟糖基化方法，该方法利用β-构型[¹⁸F]FDGs作为¹⁸F标记的前体基团，使用CuAAC点击化学进行标记。

  DOI：

  10.1039/c7nj00716g

文献信息

• Soluble Polymer-Supported Ruthenium Porphyrin Catalysts for Epoxidation, Cyclopropanation, and Aziridination of Alkenes
  作者：Jun-Long Zhang、Chi-Ming Che

  DOI：10.1021/ol0259138

  日期：2002.5.1

  [reaction: see text] Attachment of poly(ethylene glycol) (PEG) to ruthenium porphyrin via a covalent etheric bond gives soluble polymer-supported ruthenium catalysts 3-5. These catalysts exhibit high reactivity and selectivity toward alkene epoxidation with 2,6-dichloropyridine N-oxide and alkene cyclopropanation with diazo compounds. The application of these catalysts in the synthesis of unstable

  [反应：见正文]聚乙二醇（PEG）通过共价醚键连接到钌卟啉上，得到了可溶性聚合物负载的钌催化剂3-5。这些催化剂对用2，6-二氯吡啶N-氧化物进行的烯烃环氧化和用重氮化合物进行的烯烃环丙烷化表现出高反应性和选择性。已经证明了这些催化剂在不稳定有机化合物的合成中的应用。
• Ruthenium <i>meso</i>-Tetrakis(2,6-dichlorophenyl)porphyrin Complex Immobilized in Mesoporous MCM-41 as a Heterogeneous Catalyst for Selective Alkene Epoxidations
  作者：Chun-Jing Liu、Wing-Yiu Yu、Shou-Gui Li、Chi-Ming Che

  DOI：10.1021/jo981003l

  日期：1998.10.1

  A ruthenium complex of meso-tetrakis(2,6-dichlorophenyl)porphyrin, [Ru(II)(TDCPP)(CO)(EtOH)], is immobilized into mesoporous MCM-41 molecular sieves; the supported Ru catalyst can effect highly selective heterogeneous alkene epoxidations using 2,6-dichloropyridine N-oxide as terminal oxidant. Aromatic and aliphatic alkenes can be efficiently converted to their epoxides in good yields and selectivities

  将介孔四（2,6-二氯苯基）卟啉的钌络合物[Ru（II）（TDCPP）（CO）（EtOH）]固定在介孔MCM-41分子筛中；使用2,6-二氯吡啶N-氧化物作为末端氧化剂，负载型Ru催化剂可以实现高度选择性的异质烯烃环氧化。芳族和脂族烯烃可以有效地以良好的收率和选择性有效地转化为其环氧化物，而顺式烯烃，例如顺式-苯乙烯，顺式-β-甲基苯乙烯和顺式-β-氘代苯乙烯被立体定向​​地环氧化。环烯（如降冰片烯和环辛烯）的氧化可使用非均相Ru催化反应有效地进行，而这些烯烃在沸石基硅酸钛（TS-1）催化的条件下不发生反应（Murugavel，R .; Roesky， HW Angew.Chem。，Int.Ed.Engl.1997，36，477）。另一方面，Ru / M-41（m）催化剂在（+）-柠檬烯氧化中显示出尺寸选择性，其中末端C ＝ C键（相对于内部三取代的C ＝ C键）变得更容易被氧化。庞大的3
• Conformationally-locked N-glycosides: Exploiting long-range non-glycone interactions in the design of pharmacological chaperones for Gaucher disease
  作者：Javier Castilla、Rocío Rísquez、Katsumi Higaki、Eiji Nanba、Kousaku Ohno、Yoshiyuki Suzuki、Yolanda Díaz、Carmen Ortiz Mellet、José M. García Fernández、Sergio Castillón

  DOI：10.1016/j.ejmech.2014.11.002

  日期：2015.1

  Pyranoid-type glycomimetics having a cis-1,2-fused glucopyranose-2-alkylsulfany1-1,3-oxazoline (Glc-PSO) structure exhibit an unprecedented specificity as inhibitors of mammalian beta-glucosidase. Notably, their inhibitory potency against human beta-glucocerebrosidase (GCase) was found to be strongly dependent on the nature of aglycone-type moieties attached at the sulfur atom. In the particular case of omega-substituted hexadecyl chains, an amazing influence of the terminal group was observed. A comparative study on a series of Glc-PSO derivatives suggests that hydrogen bond acceptor functionalities, e.g. fluoro or methyloxycarbonyl, significantly stabilize the Glc-PSO:GCase complex. The S-(16-fluorohexadecyl)-PSO glycomimetic turned out to be a more potent GCase competitive inhibitor than ambroxol, a non glycomimetic drug currently in pilot trials as a pharmacological chaperone for Gaucher disease. Moreover, the inhibition constant increased by one order of magnitude when shifting from neutral (pH 7) to acidic (pH 5) media, a favorable characteristic for a chaperone candidate. Indeed, the fluoro-PSO derivative also proved superior to ambroxol in mutant GCase activity enhancement assays in N370S/N370S Gaucher fibroblasts. The results presented here represent a proof of concept of the potential of exploiting long-range non-glycone interactions for the optimization of glycosidase inhibitors with chaperone activity. (C) 2014 Elsevier Masson SAS. All rights reserved.
• Conformationally-Locked <i>N</i>-Glycosides with Selective β-Glucosidase Inhibitory Activity: Identification of a New Non-Iminosugar-Type Pharmacological Chaperone for Gaucher Disease
  作者：Javier Castilla、Rocío Rísquez、Deysi Cruz、Katsumi Higaki、Eiji Nanba、Kousaku Ohno、Yoshiyuki Suzuki、Yolanda Díaz、Carmen Ortiz Mellet、José M. García Fernández、Sergio Castillón

  DOI：10.1021/jm3006178

  日期：2012.8.9

  A series of conformationally locked N-glycosides having a cis-1,2-fused pyranose-1,3-oxazoline-2-thione structure and bearing different substituents at the exocyclic sulfur has been prepared. The polyhydroxylated bicyclic system was built in only three steps by treatment of the corresponding readily available 1,2-anhydrosugar with KSCN using TiO(TFA)(2) as catalyst, followed by S-alkylation and acetyl deprotection. In vitro screening against several glycosidase enzymes showed highly specific inhibition of mammalian beta-glucosidase with a marked dependence of the potency upon the nature of the exocyclic substituent. The most potent representative, bearing an S-(omega-hydroxyhexadecyl) substituent, was further assayed as inhibitor of the human lysosomal beta-glucocerebrosidase and as pharmacological chaperone in Gaucher disease fibroblasts. Activity enhancements in N370S/N370S mutants analogous to those achieved with the reference compound ambroxol were attained with a more favorable chaperone/inhibitor balance.
• A simple and highly diastereoselective preparation of glycal epoxides using the MCPBA-KF complex
  作者：Giuseppe Bellucci、Giorgio Catelani、Cinzia Chiappe、Felicia D'Andrea

  DOI：10.1016/s0040-4039(00)74426-1

  日期：1994.11

  Glycols ore converted to the corresponding epoxides in high yields by a diastereoselective one-step epoxidation using the m-chloroperoxybenzoic acid-KF complex in anhydrous dichloromethane.