6-deoxy-1,2-O-isopropylidene-α-D-xylo-hexofuranos-5-ulose | 19189-70-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-deoxy-1,2-O-isopropylidene-α-D-xylo-hexofuranos-5-ulose
• 英文别名: 6-deoxy-1,2-O-isopropylidene-α-D-xylo-hexofuranosid-5-ulose；O¹,O²-isopropylidene-α-D-xylo-6-deoxy-[5]hexosul-1,4-ose；O¹,O²-isopropylidene-α-D-xylo-6-deoxy-[5]hexosulo-1,4-ose；O¹,O²-Isopropyliden-α-D-xylo-6-desoxy-[5]hexosulo-1,4-ose；1-[(3aR,5S,6R,6aR)-6-hydroxy-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]ethanone
• CAS: 19189-70-9
• 化学式: C₉H₁₄O₅
• 分子量: 202.207
• InChiKey: ZHTBXOLUPFMEAZ-LXGUWJNJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6-deoxy-1,2-O-isopropylidene-α-D-xylo-hexofuranos-5-ulose 在 aluminum oxide 作用下， 以 吡啶 、 二氯甲烷 为溶剂， 反应 25.0h， 生成 3,6-Didesoxy-1,2-O-isopropyliden-α-D-glycero-hex-3-enofuranos-5-ulose
  参考文献：
  名称：

  Syntheses of Pyrazole Iso-C-Nucleosides

  摘要：

  3-O-Benzyl-6-deoxy-1,2-O-isopropylidene-alpha -D-xylo-hexofuranos-5-ulose (I) and 3,6-dideoxy-1,2-O-isopropylidene-alpha -D-glycero-hex-3-enofuranos-5-ulose (6) reacted with carbon disulfide and methyl iodide under basic conditions to give the alpha -oxoketene-S,S-acetals 2 and 7, respectively. Treatment of 2 and 7 with hydrazine hydrate yielded the pyrazole derivatives 3 and 8, respectively.

  DOI：

  10.1080/07328300008544133
• 作为产物：
  描述：

  1,2-O-isopropylidene-3,5,6-tri-O-orthoformyl-α-D-glucofuranose 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以40%的产率得到6-deoxy-1,2-O-isopropylidene-α-D-xylo-hexofuranos-5-ulose
  参考文献：
  名称：

  Beermann, Heinrich; Jung, Guenter; Klemer, Almuth, Liebigs Annalen der Chemie, 1982, # 8, p. 1543 - 1547

  摘要：

  DOI：

文献信息

• On the selectivity of deprotection of benzyl, mpm (4-methoxybenzyl) and dmpm (3,4-dimethoxybenzyl) protecting groups for hydroxy functions
  作者：Kiyoshi Horita、Tadao Yoshioka、Tatsuyoshi Tanaka、Yuji Oikawa、Osamu Yonemitsu

  DOI：10.1016/s0040-4020(01)90593-9

  日期：1986.1

  The 4-methoxybenzyl (MPM) protecting group for hydroxy functions is readily removed with DDQ in dichloromethane containing a small amount of water at room temperature. Under these neutral conditions, several other protecting and functional groups remained unchanged. 3,4-Dimethoxybenzyl (DMPM) groups are more reactive than MPM groups with DDQ. The benzyl (Bn) protecting group was removed by catalytic

  在室温下，用含有少量水的二氯甲烷中的DDQ可以轻松除去羟基官能团的4-甲氧基苄基（MPM）保护基。在这些中性条件下，其他几个保护和官能团保持不变。3,4-二甲氧基苄基（DMPM）基团比具有DDQ的MPM基团更具反应性。通过在阮内镍上催化氢化除去苄基（Bn）保护基。还介绍了DMPM，MPM和Bn基团的选择性脱保护。
• Specific removal of o-methoxybenzyl protection by DDQ oxidation.
  作者：Yuji Oikawa、Tadao Yoshioka、Osamu Yonemitsu

  DOI：10.1016/s0040-4039(00)86974-9

  日期：1982.1

  Methoxybenzyl protecting groups of alcohols were readily and efficiently removed with DDQ in CH2Cl2-H2O at room temperature. Under these neutral conditions, other usual protecting groups, isopropylidene, methoxymethyl, benzyloxymethyl, tetrahydropyranyl, acetyl, t-butyldimethylsilyl, benzyl, benzoyl, and tosyl, as well as functional groups, epoxide, double bond, and ketone, were remained unchanged

  室温下，在CH 2 Cl 2 -H 2 O中用DDQ可以轻松有效地除去醇的甲氧基苄基保护基。在这些中性条件下，其他常用的保护基，异丙基，甲氧基甲基，苄氧基甲基，四氢吡喃基，乙酰基，叔丁基二甲基甲硅烷基，苄基，苯甲酰基和甲苯磺酰基以及官能团，环氧化物，双键和酮保持不变。
• Hydrogenation and Hydrogenolysis with Pd/C in Poly(Ethylene Glycol) (PEG): A Practical and Recyclable Medium
  作者：S. Chandrasekhar、T. Shyamsunder、G. Chandrashekar、Ch. Narsihmulu

  DOI：10.1055/s-2003-45007

  日期：——

  Pd/C in PEG (400) has been found to be an efficient ­reusable reaction medium for hydrogenation and hydrogenolysis. Both the catalyst and PEG were recycled efficiently over four runs without appreciable loss of activity.

  研究发现，PEG（400）中的 Pd/C 是一种可重复使用的高效反应介质，可用于氢化和氢解反应。催化剂和 PEG 均可在四次运行中有效循环使用，且活性不会明显降低。
• Oxidation of carbohydrates with chromic acid The synthesis of the delta-dicarbonyl monosaccharides 6-deoxy-D-xylo-hexos-5-ulose and 6,7-dideoxy-d-xylo-heptos-5-ulose
  作者：Donald E. Kiely

  DOI：10.1016/s0008-6215(00)86203-5

  日期：1973.12

  aldehyde 3-O-benzyl-1,2-O-isopropylidene-α- d -xylo-pentodialdo-1,4-furanose (1) gave a preponderance of the corresponding 6-deoxy- and 6,7-dideoxy- l -ido derivatives (2 and 3). Oxidation of these alcohols with chromic acid gave the 5-keto derivatives 6 and 7 in high yield. The benzyl group of 6 was cleaved by catalytic hydrogenolysis, and acid-catalyzed hydrolysis of the isopropylidene group afforded

  摘要将烷基格氏试剂甲基碘化镁和溴化乙基镁添加到醛基3-O-苄基-1,2-O-异亚丙基-α-d-二甲苯基戊二醛-1,4-呋喃糖中（1）相应的6-脱氧和6,7-二脱氧-1-基衍生物（2和3）。用铬酸氧化这些醇可高产率地得到5-酮衍生物6和7。通过催化氢解裂解6的苄基，并且对异亚丙基进行酸催化的水解，得到δ-二羰基单糖6-脱氧-d-xylo-hexos-5-ulose（10）。应用于7的相同序列给出了6，7-二脱氧-d-木基-庚基-5-ulose（11）。替代8的方法是逆转氧化和氢解步骤的顺序，从2或其d-葡萄糖异构体4开始。
• Synthesis of Push-Pull Butadienes on the Basis of Hexose Derivatives
  作者：Dirk Michalik、Klaus Peseke

  DOI：10.1080/07328300008544071

  日期：2000.1

  3-O-Protected 6-deoxy-1,2-O-isopropylidene-alpha-D-xylo-hexofuranos-5-uloses 2, 4, and 10 reacted with malononitrile to furnish the Knoevenagel compounds 5, 6, and 11. Treatment of 5 and 6 with carbon disulphide and methyl iodide in the presence of sodium hydride afforded the sugar push-pull butadienes 7 and 8.