methyl 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl-(1->4)-2,3-di-O-acetyl-β-D-glucopyranoside | 139470-83-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl-(1->4)-2,3-di-O-acetyl-β-D-glucopyranoside
• 英文别名: methyl 2,2',3,3',4',6'-hexa-O-acetyl-β-maltoside；methyl 2,3,2',3',4',6'-hexa-O-acetyl-β-maltoside；[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-[(2R,3R,4S,5R,6R)-4,5-diacetyloxy-2-(hydroxymethyl)-6-methoxyoxan-3-yl]oxyoxan-2-yl]methyl acetate
• CAS: 139470-83-0；147664-43-5；52538-63-3
• 化学式: C₂₅H₃₆O₁₇
• 分子量: 608.551
• InChiKey: RMEHJXWYESKTCY-YRJWMJGDSA-N

物化性质

• 沸点：
  638.3±55.0 °C(Predicted)
• 密度：
  1.36±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.32
• 重原子数：
  42.0
• 可旋转键数：
  11.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  214.95
• 氢给体数：
  1.0
• 氢受体数：
  17.0

反应信息

• 作为反应物：
  描述：

  methyl 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl-(1->4)-2,3-di-O-acetyl-β-D-glucopyranoside 在 碘苯二乙酸 、 碘 作用下， 以 氘代氯仿 、 二氯甲烷 为溶剂， 反应 61.5h， 生成 methyl 5,6-anhydro-(2,3,4,6-tetra-O-acetyl-α-D-xylo-hexos-5-ulopyranosyl)-(1->4)-2,3-di-O-methyl-β-D-galactopyranoside
  参考文献：
  名称：

  Intramolecular 1,8-Hydrogen Abstraction Between Glucopyranose Units in a Disaccharide Model Promoted by Alkoxy Radicals

  摘要：

  DOI：

  10.1002/1521-3773(20020301)41:5<856::aid-anie856>3.0.co;2-f
• 作为产物：
  描述：

  2,3-Di-O-acetyl-1,6-anhydro-4-O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-β-D-glucopyranose 在 溴化钛(IV) 、 silver carbonate 作用下， 以 氯仿 为溶剂， 反应 28.0h， 生成 methyl 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl-(1->4)-2,3-di-O-acetyl-β-D-glucopyranoside
  参考文献：
  名称：

  Fujimaki, Itsuo; Kuzuhara, Hiroyoshi, Agricultural and Biological Chemistry, 1980, vol. 44, # 9, p. 2055 - 2060

  摘要：

  DOI：

文献信息

• C-C Bond Formation by Sequential Intramolecular Hydrogen Atom Transfer/Intermolecular Radical Allylation Reaction in Carbohydrate Systems
  作者：Elisa I. León、Ángeles Martín、Inés Pérez-Martín、Luís M. Quintanal、Ernesto Suárez

  DOI：10.1002/ejoc.201200300

  日期：2012.7

  This work was supported by the Research Programs of the Gobierno de Canarias (SolSubC200801000192 and CTQ2010‐18244) of the Ministerio de Ciencia e Innovacion, cofinanced by the Fondo Europeo de Desarrollo Regional (FEDER). I. P.‐M. thanks the Spanish Ministerio de Ciencia e Innovacion for the Research Program PIE 200930I138. L. M. Q. thanks the Consejo Superior de Investigaciones Cientificas (CSIC)

  这项工作得到了德国科学与创新部长的 Gobierno de Canarias 研究计划 (SolSubC200801000192 和 CTQ2010-18244) 的支持，并由 Fondo Europeo de Desarrollo 地区 (FEDER) 共同资助。IP-M。感谢西班牙部长级 Ciencia e Innovacion 的研究计划 PIE 200930I138。LMQ 感谢 Consejo Superior de Investigaciones Cientificas (CSIC)（I3P 计划）提供的奖学金。
• Intramolecular 1,8-Hydrogen-Atom Transfer Reactions in (1→4)-<i>O</i>-Disaccharide Systems: Conformational and Stereochemical Requirements
  作者：Cosme G. Francisco、Antonio J. Herrera、Alan R. Kennedy、Angeles Martín、Daniel Melián、Inés Pérez-Martín、Luis M. Quintanal、Ernesto Suárez

  DOI：10.1002/chem.200801414

  日期：2008.11.17

  stereochemical and conformational factors controlling the intramolecular hydrogen-atom transfer (HAT) reaction between the two pyranose units in a (1-->4)-O-disaccharide when promoted by a primary 6-O-yl radical are studied. Models with alpha-D-Glcp-(1-->4)-beta-D-Glcp, alpha-L-Rhamp-(1-->4)-alpha-D-Galp or alpha-D-Manp-(1-->4)-beta-L-Gulp skeletons led exclusively to the abstraction of the hydrogen from H--C-5'

  研究了由伯6-O-基团促进时控制（1-> 4）-O-二糖中两个吡喃糖单元之间分子内氢原子转移（HAT）反应的立体化学和构象因素。具有alpha-D-Glcp-（1-> 4）-beta-D-Glcp，alpha-L-Rhamp-（1-> 4）-alpha-D-Galp或alpha-D-Manp-（1的模型-> 4）-β-L-Gulp骨架仅导致从H--C-5'提取氢并通过九元过渡态形成1,3,5-三氧杂环丁烷环系统以稳定的船椅构造为基础。尽管如此，α-L-Rhamp-（1-> 4）-alpha-D-Glcp或alpha-D-Manp-（1-> 4）-alpha-D-Galp的衍生物专门从H- -C-1'通过七元过渡态产生糖苷间螺原酸酯。
• Intramolecular 1,8-Hydrogen Atom Transfer. Stereoselectivity of the Hexopyranos-5′-yl Radical Reactions in Hex<i>p</i>-(1→4)-Hex<i>p</i> Disaccharide Systems
  作者：Ángeles Martín、Inés Pérez-Martín、Luís M. Quintanal、Ernesto Suárez

  DOI：10.1021/jo801499d

  日期：2008.10.3

  in alpha-D-Hex p-(1-->4)-D-Hex p disaccharide models is described. These radicals are generated from a 6-O-yl radical located in the other monosaccharic unit through a 1,8-hydrogen atom transfer. The reaction, which is strongly influenced by steric and stereoelectronic effects, permits in some cases the transformation of alpha-D-Hex p-(1-->4)-D-Hex p into beta-L-Hex p-(1-->4)-D-Hex p disaccharides

  描述了在α-D-Hexp-（1→4）-D-Hex p二糖模型中六吡喃糖5'-基团的立体选择性还原。这些基团是通过1，8-氢原子转移从位于另一个单糖单元中的6-O-基团产生的。该反应在很大程度上受到空间和立体电子效应的影响，在某些情况下允许将α-D-Hexp-（1-> 4）-D-Hex p转化为beta-L-Hex p-（1- -> 4）-D-Hex p二糖，非对映选择性高。
• Regio- and Chemoselective Deprotection of Primary Acetates by Zirconium Hydrides
  作者：Marine Gavel、Thibaut Courant、Antoine Yvan Philippe Joosten、Thomas Lecourt

  DOI：10.1021/acs.orglett.8b03947

  日期：2019.4.5

  A combination of DIBAL-H and Cp2ZrCl2 is shown to promote the regioselective cleavage of primary acetates on a broad scope of substrates, ranging from carbohydrates to terpene derivatives, with a high tolerance toward protecting groups and numerous functionalities found in natural products and bioactive compounds. Apart from providing highly valuable building blocks in only two steps from biosourced raw materials, this selective de-O-acetylation should also be strongly helpful to solve selectivity issues in organic synthesis.
• Bock, Klaus; Pedersen, Henric, Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1988, vol. 42, # 2, p. 75 - 85
  作者：Bock, Klaus、Pedersen, Henric

  DOI：——

  日期：——