(+)-1-[(4S,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl]-2-(benzyloxy)ethan-1-one | 681853-94-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (+)-1-[(4S,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl]-2-(benzyloxy)ethan-1-one
• 英文别名: 1-[(4S,5S)-5-ethenyl-2,2-dimethyl-1,3-dioxolan-4-yl]-2-phenylmethoxyethanone
• CAS: 681853-94-1
• 化学式: C₁₆H₂₀O₄
• 分子量: 276.332
• InChiKey: KUOKCMLCKJFBGB-LSDHHAIUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (+)-1-[(4S,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl]-2-(benzyloxy)ethan-1-one 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 49.0h， 生成 (1R,4S,5S)-1-(benzyloxymethyl)-2-en-4,5-(O-isopropylidenedioxy)-cyclopentan-1-ol
  参考文献：
  名称：

  Preparative and Stereoselective Synthesis of the Versatile Intermediate for Carbocyclic Nucleosides:  Effects of the Bulky Protecting Groups to Enforce Facial Selectivity

  摘要：

  The preparative and stereoselective synthesis (45-50% overall yields) of the target compound 17 has been accomplished from D-ribose. The bulky protecting groups such as TBDPS and Trityl enforced the facial selectivity during Grignard reaction to give the tertiary beta-allylic alcohol 16 as the sole product, which was oxidatively rearranged to the key molecule 17 in excellent yield.

  DOI：

  10.1021/jo0356762
• 作为产物：
  描述：

  5-O-benzyl-2,3-O-isopropylidene-D-ribofuranose 在 草酰氯 、 potassium tert-butylate 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 (+)-1-[(4S,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl]-2-(benzyloxy)ethan-1-one
  参考文献：
  名称：

  STEREOSELECTIVE SYNTHESIS OF 3-HYDROXYMETHYL-D-CYCLOPENTENONE, THE VERSATILE INTERMEDIATE FOR THE SYNTHESIS OF CARBOCYCLIC NUCLEOSIDES

  摘要：

  The preparative and stereoselective synthesis (45 - 50% overall yields, >50 g scale) of the key carbasugars 7a-d was achieved from D-ribose via stereoselective Grignard reaction and oxidative rearrangement as key reactions.

  DOI：

  10.1081/ncn-200061832

文献信息

• Preparative Synthesis of the Key Intermediate, (4<i>R</i>,5<i>R</i>)-3-Benzyloxymethyl-4,5-isopropylidenedioxycyclopent-2-enone for Carbocyclic Nucleosides
  作者：Hyung Ryong Moon、Won Jun Choi、Hea Ok Kim、Lak Shin Jeong

  DOI：10.1246/cl.2004.506

  日期：2004.5

  (4R,5R)-3-Benzyloxymethyl-4,5-isopropylidenedioxycyclopent-2-enone (1), a versatile intermediate for the synthesis of carbocyclic nucleosides was synthesized from D-ribose in 10 steps and 26% overa...

  (4R,5R)-3-Benzyloxymethyl-4,5-isopropylidenedioxycyclopent-2-enone (1) 是一种用于合成碳环核苷的通用中间体，由 D-核糖分 10 步合成，合成率 26%。
• Preparative and Stereoselective Synthesis of the Versatile Intermediate for Carbocyclic Nucleosides:  Effects of the Bulky Protecting Groups to Enforce Facial Selectivity
  作者：Won Jun Choi、Hyung Ryong Moon、Hea Ok Kim、Byul Nae Yoo、Jeong A Lee、Dae Hong Shin、Lak Shin Jeong

  DOI：10.1021/jo0356762

  日期：2004.4.1

  The preparative and stereoselective synthesis (45-50% overall yields) of the target compound 17 has been accomplished from D-ribose. The bulky protecting groups such as TBDPS and Trityl enforced the facial selectivity during Grignard reaction to give the tertiary beta-allylic alcohol 16 as the sole product, which was oxidatively rearranged to the key molecule 17 in excellent yield.
• STEREOSELECTIVE SYNTHESIS OF 3-HYDROXYMETHYL-D-CYCLOPENTENONE, THE VERSATILE INTERMEDIATE FOR THE SYNTHESIS OF CARBOCYCLIC NUCLEOSIDES
  作者：Won Jun Choi、Hyung Ryong Moon、Hea Ok Kim、Young Mi Ko、Hye Jin Kim、Jeong A. Lee、Kang Man Lee、Mi Kyung Yun、Dae Hong Shin、Moon Woo Chun、Yhun Y. Sheen、Kilhyoun Kim、Lak Shin Jeong

  DOI：10.1081/ncn-200061832

  日期：2005.4.1

  The preparative and stereoselective synthesis (45 - 50% overall yields, >50 g scale) of the key carbasugars 7a-d was achieved from D-ribose via stereoselective Grignard reaction and oxidative rearrangement as key reactions.