[(2R,3S)-3-[tert-butyl(dimethyl)silyl]oxy-2-hydroxyhex-5-enyl] benzoate | 180986-88-3

• 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: [(2R,3S)-3-[tert-butyl(dimethyl)silyl]oxy-2-hydroxyhex-5-enyl] benzoate
• CAS: 180986-88-3
• 化学式: C₁₉H₃₀O₄Si
• 分子量: 350.53
• InChiKey: XXTNRPUPYUNKGH-SJORKVTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.17
• 重原子数：
  24
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [(2R,3S)-3-[tert-butyl(dimethyl)silyl]oxy-2-hydroxyhex-5-enyl] benzoate 在 臭氧 、 三苯基膦 作用下， 生成 5-O-benzoyl-3-O-tert-butyldimethylsilyl-2-deoxy-β-D-erytro-pentofuranose 、 5-O-benzoyl-3-O-tert-butyldimethylsilyl-2-deoxy-α-D-erytro-pentofuranose
  参考文献：
  名称：

  (R)-2,3-Cyclohexylideneglyceraldehyde: A versatile intermediate for sugar modified dideoxynucleosides

  摘要：

  (R)-2,3-Cyclohexylideneglyceraldeyde 1 has been found to be a useful intermediate for the convenient synthesis of both threo- and erythro- forms of functionally rich 2-deoxypentofuranoses, possible precursors of sugar modified 2',3'-dideoxynucleosides. This has been exemplified by the exploitation of its major allylation product 2b for a short synthesis of 4 and 8 and subsequent transformation of 8 to threo 3-azido-2,3-dideoxy-pentofuranose 9. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00325-x
• 作为产物：
  描述：

  1(S)-[(2R)-1,4-dioxaspiro[4.5]decanyl]-3-buten-1-ol 在 咪唑 、 三氟乙酸 、 三甲胺 作用下， 以 二氯甲烷 为溶剂， 反应 5.5h， 生成 [(2R,3S)-3-[tert-butyl(dimethyl)silyl]oxy-2-hydroxyhex-5-enyl] benzoate
  参考文献：
  名称：

  (R)-2,3-O-Cyclohexylideneglyceraldehyde, a Versatile Intermediate for Asymmetric Synthesis of Homoallyl and Homopropargyl Alcohols in Aqueous Medium

  摘要：

  Zn-mediated allylation and propargylation of (R)-2,3-O-cyclohexylideneglyceraldehyde (1) in aqueous medium following Luche's procedure afforded the anti homoallylic 3 and homopropargylic 8 alcohols in good yield and with high stereoselectivity, Crotylation of 1 under similar conditions afforded appreciable amounts of erythro-5 and threo-6 alcohols. In each case, the diastereo alcohols are separable by column chromatography. Compound 8 on appropriate chemical manipulation of its functionalities gave the (S)-enantiomer of (R)-13, a useful synthon of LTB(4). Compound 3 on chemical elaboration afforded a diversely functionalized triol derivative 15, a potentially useful synthon for many bioactive compounds.

  DOI：

  10.1021/jo9604696

文献信息

• (<i>R</i>)-2,3-<i>O</i>-Cyclohexylideneglyceraldehyde, a Versatile Intermediate for Asymmetric Synthesis of Homoallyl and Homopropargyl Alcohols in Aqueous Medium
  作者：Angshuman Chattopadhyay

  DOI：10.1021/jo9604696

  日期：1996.1.1

  Zn-mediated allylation and propargylation of (R)-2,3-O-cyclohexylideneglyceraldehyde (1) in aqueous medium following Luche's procedure afforded the anti homoallylic 3 and homopropargylic 8 alcohols in good yield and with high stereoselectivity, Crotylation of 1 under similar conditions afforded appreciable amounts of erythro-5 and threo-6 alcohols. In each case, the diastereo alcohols are separable by column chromatography. Compound 8 on appropriate chemical manipulation of its functionalities gave the (S)-enantiomer of (R)-13, a useful synthon of LTB(4). Compound 3 on chemical elaboration afforded a diversely functionalized triol derivative 15, a potentially useful synthon for many bioactive compounds.
• (R)-2,3-Cyclohexylideneglyceraldehyde: A versatile intermediate for sugar modified dideoxynucleosides
  作者：Angshuman Chattopadhyay

  DOI：10.1016/s0957-4166(97)00325-x

  日期：1997.8

  (R)-2,3-Cyclohexylideneglyceraldeyde 1 has been found to be a useful intermediate for the convenient synthesis of both threo- and erythro- forms of functionally rich 2-deoxypentofuranoses, possible precursors of sugar modified 2',3'-dideoxynucleosides. This has been exemplified by the exploitation of its major allylation product 2b for a short synthesis of 4 and 8 and subsequent transformation of 8 to threo 3-azido-2,3-dideoxy-pentofuranose 9. (C) 1997 Elsevier Science Ltd.