2-desoxy-3,7-anhydro-4,5,6,8-tetra-O-acetyl-D-glucooctonic acid | 34010-29-2

• 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: 2-desoxy-3,7-anhydro-4,5,6,8-tetra-O-acetyl-D-glucooctonic acid
• 英文别名: 4,5,6,8-tetra-O-acetyl-3,7-anhydro-2-deoxy-D-glycero-D-gulo-octonic acid；4,5,6,7-tetra-O-acetyl-3,7-anhydro-2-deoxy-D-glycero-D-gulo-octonic acid；2-((2S,3S,4R,5R,6R)-3,4,5-triacetoxy-6-(acetoxymethyl)tetrahydro-2H-pyran-2-yl)acetic acid；2-[(2S,3S,4R,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]acetic acid
• CAS: 34010-29-2
• 化学式: C₁₆H₂₂O₁₁
• 分子量: 390.344
• InChiKey: QMDHNPNDVMZVMN-FHXAZYNBSA-N

物化性质

• 沸点：
  492.1±35.0 °C(Predicted)
• 密度：
  1.34±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  27
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  152
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  2-desoxy-3,7-anhydro-4,5,6,8-tetra-O-acetyl-D-glucooctonic acid 在 氯化亚砜 作用下， 反应 2.0h， 生成 4,5,6,8-tetra-O-acetyl-3,7-anhydro-2-deoxy-D-glycero-D-gulo-octonoyl chloride
  参考文献：
  名称：

  Chemoenzymatic synthesis of enantiomerically enriched aminoalkenols and glycosides thereof

  摘要：

  1-t-Butoxycarbonylamido-3-pentene-1-ol 3 and 2-azido-4-phenyl-3-butene-1-ol 4 were enantiomerically enriched by enzymatic acetylation using various lipases and esterases (CHIRAZYM) to give acetylated compounds 5 and 7, respectively. Compound 3 gave the best results (E = 94) with Candida antarctica A lipase (CHIRAZYM L-5), whereas 4 could not be separated into the enantiomers with satisfactory E values. The absolute configurations were proven for both compounds via independently prepared derivatives. Both enantiomers of 5, as well as racemic 7, were N-deblocked and condensed with octonic acid derivatives 14 to give the corresponding C-glycosides 17 and 22 after deprotection of the intermediates in good overall yield. Compound 4 was similarly condensed with glucose imidate 11 to give the diastereomeric O-glycosides 13 after deprotection. The latter glycosides were prepared as precursors for the generation of the corresponding aldehydes as substrates for aldolase catalyzed reactions. (C) 2000 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(00)00294-9
• 作为产物：
  描述：

  2,2-dimethyl-5-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl)-1,3-dioxan-4,6-dione 在 溶剂黄146 作用下， 反应 2.0h， 生成 2-desoxy-3,7-anhydro-4,5,6,8-tetra-O-acetyl-D-glucooctonic acid
  参考文献：
  名称：

  Reaction of Meldrum's acid with d -mannose and l -arabinose

  摘要：

  DOI：

  10.1016/0008-6215(92)80049-7

文献信息

• Reversing Reactivity: Stereoselective Desulfurative 1,2-<i>trans</i>-<i>O</i>-Glycosylation of Anomeric Thiosugars with Carboxylic Acids under Copper or Cobalt Catalysis
  作者：Nedjwa Bennai、Amélie Chabrier、Maha I. Fatthalla、Christine Tran、Expédite Yen-Pon、Mohamed Belkadi、Mouâd Alami、Laurence Grimaud、Samir Messaoudi

  DOI：10.1021/acs.joc.0c00766

  日期：2020.7.17

  We have discovered a new mode of reactivity of 1-thiosugars in the presence of Cu(II) or Co(II) for a stereoselective O-glycosylation reaction. The process involves the use of a catalytic amount of Cu(acac)2 or Co(acac)2 and Ag2CO3 as an oxidant in α,α,α-trifluorotoluene. Moreover, this protocol turned out to have a broad scope, allowing the preparation of a wide range of complex substituted O-glycoside

  我们已经发现在立体选择性O-糖基化反应的Cu（II）或Co（II）存在下1-硫糖的反应性的新模式。该方法涉及使用催化量的Cu（acac）2或Co（acac）2和Ag 2 CO 3作为α，α，α-三氟甲苯中的氧化剂。而且，该方案证明具有广泛的范围，允许以良好的至优异的产率和排他的1,2-反式选择性制备多种复杂的取代的O-糖苷酯。还证明了通过这种方法对药物进行后期修饰。为了更深入地了解反应机理，进行了循环伏安法。
• Synthesis and Structural Analysis of Cyclic Oligomers Consisting of Furanoid and Pyranoid ε-Sugar Amino Acids
  作者：Renate M. van Well、Luciana Marinelli、Kees Erkelens、Gijsbert A. van der Marel、Antonio Lavecchia、Herman S. Overkleeft、Jacques H. van Boom、Horst Kessler、Mark Overhand

  DOI：10.1002/ejoc.200300031

  日期：2003.6

  Cyclic oligomers composed of amide-linked furanoid (i.e., 1, 3) and pyranoid (i.e., 2, 4) ϵ-sugar amino acids (SAAs) were prepared by a cyclization/cleavage approach with use of the oxime resin. These cyclic homooligomers were constructed by use of the known N-Boc protected furanoid ϵ-SAA 11 and the novel pyranoid hydroxymethylene homologue 22. Conformational analysis of cyclic trimer 1 by an unrestrained

  由酰胺连接的呋喃（即 1, 3）和吡喃（即 2, 4）ε-糖氨基酸 (SAA) 组成的环状低聚物是通过环化/裂解方法使用肟树脂制备的。这些环状同低聚物是通过使用已知的 N-Boc 保护的呋喃 ϵ-SAA 11 和新型吡喃羟基亚甲基同系物 22 构建的。通过无限制的模拟退火技术对环状三聚体 1 的构象分析表明，残基的呋喃环在 I 之间翻转扭曲（北，P = 0°）和包络（南，P = 167°）构象。此外，连接羰基官能团（即C2）的侧链被证明是刚性的，而其他侧链（C7）在构象上是柔性的。对于三聚体 2 中的吡喃 ϵ-SAA II 残基的侧链，观察到类似的构象行为，但吡喃环椅构象在计算过程中保持稳定。这些构象细节可能对未来基于 SAA 的人工受体或肽模拟物的设计具有重要意义。(© Wiley-VCH Verlag GmbH & Co. KGAA, 69451 Weinheim, Germany, 2003)
• Preparation of glycosyl amino acids as building blocks for the combinatorial synthesis of neoglycoconjugates
  作者：Thomas Ziegler、Dirk Röseling、Lakshminarayanapuram R. Subramanian

  DOI：10.1016/s0957-4166(02)00212-4

  日期：2002.6

  Several neoglycosyl amino acids possessing a sugar residue, a spacer and trifunctional amino acid moiety were synthesized both in solution and solid phase by activating the carboxylic group as its pentafluorophenyl ester for condensation. The methodology is useful for application in combinatorial syntheses of neoglycoconjugates as potential mimics for oligosaccharides. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Zhdanov, Yu. A.; Uzlova, L. A.; Glebova, Z. I., Doklady Chemistry, 1980, vol. 255, p. 552 - 555
  作者：Zhdanov, Yu. A.、Uzlova, L. A.、Glebova, Z. I.

  DOI：——

  日期：——