1,2:5,6-di-O-cyclohexylidene-α-D-ribo-3-hexofuranose-3-ulose | 18546-21-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,2:5,6-di-O-cyclohexylidene-α-D-ribo-3-hexofuranose-3-ulose
• 英文别名: 1,2:5,6-di-O-cyclohexylidene-α-D-ribo-hexofuranos-3-ulose；1,2:5,6-di-O-cyclohexylidene-α-D-ribohexofuranos-3-ulose；1,2:5,6-DI-O-Cyclohexylidene-alpha-D-ribo-hexofuranose-3-ulose；(3aR,5R,6aS)-5-[(3R)-1,4-dioxaspiro[4.5]decan-3-yl]spiro[3a,6a-dihydrofuro[2,3-d][1,3]dioxole-2,1'-cyclohexane]-6-one
• CAS: 18546-21-9
• 化学式: C₁₈H₂₆O₆
• 分子量: 338.401
• InChiKey: ATKCJVLOYSNJNI-DTZQCDIJSA-N

物化性质

• 熔点：
  119-121 °C
• 沸点：
  482.6±45.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  24
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.94
• 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：

  1,2:5,6-di-O-cyclohexylidene-α-D-ribo-3-hexofuranose-3-ulose 在 吡啶 、 magnesium,2-methylpropane,bromide 作用下， 以 乙醚 、 苯 为溶剂， 反应 0.25h， 生成 (3A'r,5'R,6'R,6A'r)-5'-[(2R)-1,4-二氧杂螺[4.5]癸-2-基]四氢螺[环己烷-1,2'-呋喃并[2,3-d][1,3]二氧杂环戊烯]-6'-基甲烷磺酸酯
  参考文献：
  名称：

  格氏试剂在碳水化合物合成中的应用。一、脱氧和支链脱氧糖的合成

  摘要：

  两种支链脱氧糖，甲基 5,6-O-cyclohexylidene-3-deoxy-2-C-methyl-β-D-arabino-hexofuranoside 及其 α-D-ribo 异构体，可以通过一步轻松制备甲基 5,6-O-cyclohexylidene-3-O-mesyl-β-D-allofuranoside (3a) 与甲基碘化镁的反应。类似地，相应的 α-甲磺酸酯 (4a) 得到 5,6-O-cyclohexylidene-3-deoxy-2-C-methyl-α-D-ribo-hexofuranoside 甲酯。已证明这些反应涉及 1,2-氢化物转移。3a 和 4a 与叔丁基溴化镁的反应分别产生两种脱氧糖，甲基 5,6-O-cyclohexylidene-3-deoxy-β-D-arabino-hexofuranoside 和相应的 α-D-ribo 异构体。在与格氏试剂的某些反应条件下，磺酸盐

  DOI：

  10.1246/bcsj.53.222
• 作为产物：
  描述：

  1,2:5,6-二-O-环己亚基-alpha-D-呋喃葡萄糖 在 戴斯-马丁氧化剂 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 4.0h， 以74%的产率得到1,2:5,6-di-O-cyclohexylidene-α-D-ribo-3-hexofuranose-3-ulose
  参考文献：
  名称：

  Rao, H. Surya Prakash; Muralidharan, P.; Pria, S., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1997, vol. 36, # 9, p. 816 - 818

  摘要：

  DOI：

文献信息

• Synthesis of 2-<i>C</i>-Methyl-<scp>D</scp>-erythritol and 2-<i>C</i>-Methyl-<scp>L</scp>-threitol; Determination of the Absolute Configuration of 2-<i>C</i>-Methyl-1,2,3,4-butanetetrol Isolated from<i>Phlox sublata L</i>
  作者：Isao SAKAMOTO、Kazuo ICHIMURA、Hiroshi OHRUI

  DOI：10.1271/bbb.64.1915

  日期：2000.1

  2-C-Methyl-D-erythritol (A) and 2-C-methyl-L-threitol (B) were respectively synthesized from D-glucose and D-galactose. The 2-C-methyl-1,2,3,4-butanetetrol compound (C) recently isolated from Phlox sublata L was confirmed to be A by comparing the CD and 1H-NMR spoectra of its tri-O-benzoate with those of A and B.

  2-C-甲基-D-赤藓糖醇（A）和2-C-甲基-L-苏糖醇（B）分别由D-葡萄糖和D-半乳糖合成。最近从裂叶紫萝属植物中分离得到的2-C-甲基-1,2,3,4-丁四醇化合物（C）通过对比其三-O-苯甲酸酯的圆二色谱和氢核磁共振谱与A、B的数据，确认该化合物为A。
• Readily available new pyridyl alcohols derived from d-glucose as ligands for the enantioselective addition of diethylzinc to aldehydes
  作者：Hanmin Huang、Zhuo Zheng、Huilin Chen、Changmin Bai、Junwei Wang

  DOI：10.1016/s0957-4166(03)00212-x

  日期：2003.5

  A series of new chiral ligands derived from D-glucose has been synthesized and applied in the enantioselective addition of diethylzinc to aldehydes. Up to 94.1% e.e. was obtained in the ethylation reactions. In contrast to the ligands derived from D-fructose, ligands derived from D-glucose gave the opposite asymmetric induction. (C) 2003 Elsevier Science Ltd. All rights reserved.
• Rao, H. Surya Prakash; Muralidharan, P.; Pria, S., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1997, vol. 36, # 9, p. 816 - 818
  作者：Rao, H. Surya Prakash、Muralidharan, P.、Pria, S.

  DOI：——

  日期：——
• Novel 3-C-aminomethyl-hexofuranose-derived thioureas and their testing in asymmetric catalysis
  作者：Māris Turks、Evija Rolava、Dmitrijs Stepanovs、Anatoly Mishnev、Dean Marković

  DOI：10.1016/j.tetasy.2015.07.003

  日期：2015.9

  Both 1,2:5,6-di-O-isopropylidene- and 1,2:5,6-di-O-cyclohexylidene-alpha-D-glucofuranose-derived ketones provided the corresponding branched 3-C-nitromethyl-congeners in the Henry reaction with nitromethane anion. Reduction of the nitro moiety followed by derivatization with iso(thio)cyanates gave 3-C-aminomethyl-hexofuranose-derived (thio)ureas. The relative configuration of the products in each series was unambiguously established by X-ray analysis. The title products were shown to act as organocatalysts in Friedel Crafts alkylations of indoles with beta-nitrostyrenes and in Michael additions of nitromethane to trans-chalcones. (C) 2015 Elsevier Ltd. All rights reserved.
• Carbohydrate-based synthesis of crocacin: stereoselective Heck reaction of carbohydrate 5,6-ene- and 5,6-yne-derivatives with aromatic halides
  作者：Mukund K. Gurjar、Tushar P. Khaladkar、Ramdas G. Borhade、A. Murugan

  DOI：10.1016/s0040-4039(03)01256-5

  日期：2003.7

  The Heck reaction between a carbohydrate 5,6-ene derivative 9 and an aromatic halide exclusively gave rise to the beta-carbohydrate-substituted trans-styrene derivative 8; while the corresponding Wittig reaction produced a cis/trans mixture in which the cis-isomer predominated. The application of the Heck reaction is described to synthesize the intermediate 5, commonly used in the synthesis of members of the crocacin family. (C) 2003 Elsevier Science Ltd. All rights reserved.