formyl C-mannofuranoside diacetonide | 154127-61-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: formyl C-mannofuranoside diacetonide
• 英文别名: (3aS,4R,6R,6aS)-4-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxole-6-carbaldehyde
• CAS: 154127-61-4
• 化学式: C₁₃H₂₀O₆
• 分子量: 272.298
• InChiKey: FYSCJLFMCZMMFE-LXUNUROVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  formyl C-mannofuranoside diacetonide 在 palladium on activated charcoal 重铬酸吡啶 、 硫酸 、 氢气 、 氧气 、 sodium hydride 、 溶剂黄146 、 三乙胺 、 sodium iodide 、 copper(l) chloride 、 palladium dichloride 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 丁酮 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 33.0h， 生成 (3aR,5S,6R,6aR)-6-Hydroxy-5-((S)-hydroxy-phenyl-methyl)-tetrahydro-furo[3,2-b]furan-2-one
  参考文献：
  名称：

  Synthesis and antitumor activity of goniofufurone analogues

  摘要：

  Synthesis and antitumor activity of goniofufurone analogues 15, 16, 17, 33, and 46 is reported. Key step in the synthesis is Pd (II) mediated oxidative cyclisation of vinyl-(hydroxy) furans 18, 19 to the corresponding lactols 32, 43. Cytotoxicities of 15, 16, 17, 33, and 46 tested against six human cancer cell lines are reported. Change of stereochemistry at C-5, C-6 and C-7 position of goniofufurone (1) did not enhance the cytotoxicities significantly.

  DOI：

  10.1016/s0968-0896(99)00164-9
• 作为产物：
  描述：

  2-(2,3:5,6-Di-O-isopropylidene-β-D-mannofuranosyl)thiazole 在 sodium tetrahydroborate 、 三氟甲烷磺酸甲酯 、 mercury dichloride 作用下， 生成 formyl C-mannofuranoside diacetonide
  参考文献：
  名称：

  Thiazole-based synthesis of C-glycosyl aldehydes

  摘要：

  The formylation at the anomeric carbon of the model sugars 2,3,4,6-tetra-O-benzyl-D-glucopyranose and 2,3:5,6-di-O-isopropylidene-D-mannofuranose is carried out by addition of 2-lithiothiazole to the corresponding lactones followed by reductive dehydroxylation and thiazole to formyl deblocking.

  DOI：

  10.1016/s0040-4039(00)79319-1

文献信息

• Formyl<i>C</i>-Glycosides as Precursors to Glycosyl Nitrile Oxides and Nitrones
  作者：Alessandro Dondoni、Pier Paolo Giovannini

  DOI：10.1055/s-2002-33643

  日期：——

  three steps, are readily condensed with N-benzylhydroxylamine and hydroxylamine to give the corresponding glycosyl nitrones and oximes respectively. The latter imino derivatives are the precursors to nitrile oxides via the N-bromosuccinimide method.

  通过糖内酯的噻唑基甲酰化三步制备甲酰基 C-糖苷，很容易与 N-苄基羟胺和羟胺缩合，分别得到相应的糖基硝酮和肟。后一种亚氨基衍生物是通过 N-溴代琥珀酰亚胺法生成腈氧化物的前体。
• Total Synthesis of (−)-Orthodiffenes A and C
  作者：Jun Liu、Yi Liu、Xing Zhang、Chaoli Zhang、Yangguang Gao、LinLin Wang、Yuguo Du

  DOI：10.1021/jo301829p

  日期：2012.11.2

  orthodiffenes A and C, including their absolute stereochemistry. The key steps of our total synthesis involved cis-fused tetrahydrofuran cyclization, one-pot deprotection–lactonization, and intramolecular benzoyl migration according to a biosynthetic hypothesis of orthodiffenes.

  （-）-正交二烯A和C的高效，简捷合成是从容易获得的手性合成子，d-甘露糖和d-乳酸乙酯分八步完成的。我们的工作证实了正二烯A和C的完整结构，包括其绝对的立体化学。根据原邻二烯的生物合成假设，我们全合成的关键步骤包括顺式融合的四氢呋喃环化，一锅脱保护-内酯化和分子内苯甲酰迁移。
• Synthesis of C-disaccharides from C-formyl glycosides
  作者：Alessandro Dondoni、Alessia Boscarato、Helene Zuurmond

  DOI：10.1016/0040-4039(96)01667-x

  日期：1996.10

  ranoside (1) and 2,3,4,6-tetra-O-benzyl-d-galactopyranoside (2) with the protected galactose 6-phosphorane 3 leads to the corresponding olefins which upon hydrogenolysis give β (1 →6′)-linked C-disaccharides 6 and 8 in 56 and 72% yield, respectively.

  C-甲酰基2,3：5,6-二-O-异亚丙基-d-呋喃呋喃糖苷（1）与2,3,4,6-四-O-苄基-d-吡喃半乳糖苷（2）之间的偶联半乳糖6-磷烷3生成相应的烯烃，这些烯烃在氢解后分别以56％和72％的收率得到β（1→6'）连接的C-二糖6和8。
• Thiazole-Based Synthesis of Formyl C-Glycosides
  作者：Alessandro Dondoni、Marie-Christine Scherrmann

  DOI：10.1021/jo00100a050

  日期：1994.10

  A method for the installation of the formyl group at the anomeric position of pyranoses and furanoses starting from the corresponding lactones has been developed. The strategy involves the addition of 2-lithiothiazole to the sugar lactone, followed by the silane reduction of the acetylated resultant ketol and the unmasking of the formyl group from the thiazole ring. All steps have been studied in some details to improve chemical efficiency and stereochemical control. Hence, reversed alpha:beta ratios of ketols were found in kinetic and thermodynamic mixtures, the former being consistent with a steric effect control of the substituents and the latter by the electronic effect of the ring oxygen. Seven sugar aldehydes with different D-pyranosidic (2,3,4,6-tetra-O-benzyl-gluco, -galacto, and -manno, 2-azido-3,4,6-tri-O-benzyl-2-deoxy-galacto) and D-furanosidic moieties (5-O-benzyl-2,3-isopropylidene-ribo; 2,3,5-tri-O-benzyl-ribo; 2,3:5,6-di-O-isopropylidene-manno) were prepared in 52-65% isolated overall yield from the corresponding lactone.
• Synthesis of α- and β-<scp>d</scp>-(1→6)-<i>C</i>-Disaccharides by Wittig Olefination of Formyl <i>C</i>-Glycosides with Glycopyranose 6-Phosphoranes
  作者：Alessandro Dondoni、Helene M. Zuurmond、Alessia Boscarato

  DOI：10.1021/jo971177n

  日期：1997.11.1

  The synthesis of (1-->6)-C-disaccharides by Wittig condensation of formyl C-glycofuranosides and pyranosides with galacto-and glucopyranose B-phosphoranes is described herein. The method involves the coupling of the sugar aldehydes with the ylides and the reduction of the double bond of the resulting sugar alkenes, in most of the cases by catalytic hydrogenation. The reduction with nickel boride or diimide is employed in some special cases. O-Benzyl protective groups are removed by catalytic hydrogenation either in the course of the reduction of the double bond or in a subsequent step, while O-isopropylidene groups are cleaved by treatment with Amberlite IR-120. In this way, eight free beta-D-(1-->6)-C-disaccharides have been prepared in 26-61% overall yield starting from B-linked formyl C-glycosides. These include C-linked analogues of the biologically active disaccharides allolactose (Gal beta 1,6Glc), gentiobiose (Glc beta 1,6Glc), and N-acetylamino disaccharides (GalNHAc beta,6Gal and GalNHAc beta 1,6Glc). Moreover, the synthesis of two alpha-D-(1-->6)-C-disaccharides is described from formyl C-furanosides. The limiting condition of the synthesis of these stereoisomers is the configurational instability of the alpha-linked formyl C-glycosides under the basic conditions of the Wittig olefination.