(2R,3R,4R,5R,6S)-1,2:4,5-di-O-isopropylidene-non-8-yne-1,2,3,4,5,6-hexol | 148616-97-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3R,4R,5R,6S)-1,2:4,5-di-O-isopropylidene-non-8-yne-1,2,3,4,5,6-hexol
• 英文别名: 1,2,3-trideoxy-5,6:8,9-di-O-isopropylidene-D-glycero-D-galacto-1-yno-nonitol；(1S)-1-[(4R,5S)-5-[(R)-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-hydroxymethyl]-2,2-dimethyl-1,3-dioxolan-4-yl]but-3-yn-1-ol
• CAS: 148616-97-1
• 化学式: C₁₅H₂₄O₆
• 分子量: 300.352
• InChiKey: YUIAWFLXCKPJOP-CLPYTZEMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  77.4
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2R,3R,4R,5R,6S)-1,2:4,5-di-O-isopropylidene-non-8-yne-1,2,3,4,5,6-hexol 在 N-溴代丁二酰亚胺(NBS) 、 臭氧 、 silver nitrate 、 溶剂黄146 作用下， 以 二甲基硫 、 水 、 丙酮 为溶剂， 反应 63.0h， 生成 3-脱氧-D-甘油-D-乳-2-吡喃壬酮糖酸
  参考文献：
  名称：

  Practical Synthesis of 2-Keto-3-deoxy-d-glycero-d-galactononulosonic Acid (KDN)

  摘要：

  Reaction of propargylmagnesium bromide with 2,3;5,6-di-O-Isopropylidene-D-mannonolactone followed by highly stereoselective reduction of the so-formed lactol with sodium borohydride gives a syn-diol from which practical syntheses of 2-keto-3-deoxy-D-glycero-D-galactononulosonic acid (KDN) and various partially protected derivatives have been achieved all of which feature the oxidative unmasking of the alpha-keto acid moiety from the alkyne.

  DOI：

  10.1021/ol202773t
• 作为产物：
  描述：

  2,3:5,6-二-O-异亚丙基-D-甘露糖酸-1,4-内酯 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 甲醇 、 甲苯 为溶剂， 反应 2.0h， 生成 1,2,3-trideoxy-5,6:8,9-di-O-isopropylidene-D-glycero-D-galacto-1,2-dieno-nonitol 、 1,2,3-trideoxy-5,6:8,9-di-O-isopropylidene-D-glycero-D-talo-1-yno-nonitol 、 (2R,3R,4R,5R,6S)-1,2:4,5-di-O-isopropylidene-non-8-yne-1,2,3,4,5,6-hexol
  参考文献：
  名称：

  Practical Synthesis of 2-Keto-3-deoxy-d-glycero-d-galactononulosonic Acid (KDN)

  摘要：

  Reaction of propargylmagnesium bromide with 2,3;5,6-di-O-Isopropylidene-D-mannonolactone followed by highly stereoselective reduction of the so-formed lactol with sodium borohydride gives a syn-diol from which practical syntheses of 2-keto-3-deoxy-D-glycero-D-galactononulosonic acid (KDN) and various partially protected derivatives have been achieved all of which feature the oxidative unmasking of the alpha-keto acid moiety from the alkyne.

  DOI：

  10.1021/ol202773t

文献信息

• Thermal, Spectroscopic, and Crystallographic Analysis of Mannose-Derived Linear Polyols
  作者：Ida Mattsson、Manu Lahtinen、Anssi Peuronen、Abhijit Sau、Andreas Gunell、Tiina Saloranta-Simell、Reko Leino

  DOI：10.1021/acs.cgd.8b00263

  日期：2018.5.2

  racemic form has been conducted. The binary melting point diagram of the system was determined by differential scanning calorimetry analysis, and the obtained results, along with structure determination by single crystal X-ray diffraction, confirmed that allylated mannose forms a true racemate. Further examination by powder X-ray diffraction and CP MAS 13C NMR spectroscopy revealed polymorphism both in the

  先前已证明在Barbier型金属介导的d-甘露糖烯丙基化反应中形成的主要非对映异构体在固态和溶液中均具有完美的线性构象，从而形成氢键网络并随后从水溶液中聚集。搅拌下溶解。在此，对烯丙基化的d-甘露糖及其外消旋形式的固态结构进行了全面研究。通过差示扫描量热法分析确定该系统的二元熔点图，并且获得的结果以及通过单晶X射线衍射确定的结构证实了烯丙基化的甘露糖形成了真正的外消旋体。通过粉末X射线衍射和CP MAS 13C NMR光谱进一步检查，发现纯对映体和外消旋体均具有多态性。另外，制备了烯丙基化的d-甘露糖的炔丙基化和氢化的类似物，并进行了热分析和光谱分析。成功确定了炔丙基化化合物的晶体结构，显示出与烯丙基化的d-甘露糖相似的线性分子构象。两种新化合物同样在水中表现出聚集行为，进一步证实了低能线性构象在这些棒状甘露糖衍生物的这种异常行为中起着重要作用。
• Practical Synthesis of 2-Keto-3-deoxy-<scp>d</scp>-glycero-<scp>d</scp>-galactononulosonic Acid (KDN)
  作者：David Crich、Chandrasekhar Navuluri

  DOI：10.1021/ol202773t

  日期：2011.12.2

  Reaction of propargylmagnesium bromide with 2,3;5,6-di-O-Isopropylidene-D-mannonolactone followed by highly stereoselective reduction of the so-formed lactol with sodium borohydride gives a syn-diol from which practical syntheses of 2-keto-3-deoxy-D-glycero-D-galactononulosonic acid (KDN) and various partially protected derivatives have been achieved all of which feature the oxidative unmasking of the alpha-keto acid moiety from the alkyne.