(5S,6R)-3-hydroxymethyl-5-O-tert-butyl-diphenylsilyl-6,7-O-cyclohexylidene-5,6,7-trihydroxy-hept-1-ene | 1312413-13-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (5S,6R)-3-hydroxymethyl-5-O-tert-butyl-diphenylsilyl-6,7-O-cyclohexylidene-5,6,7-trihydroxy-hept-1-ene
• 英文别名: 2-[(2S)-2-[tert-butyl(diphenyl)silyl]oxy-2-[(3R)-1,4-dioxaspiro[4.5]decan-3-yl]ethyl]but-3-en-1-ol
• CAS: 1312413-13-0
• 化学式: C₃₀H₄₂O₄Si
• 分子量: 494.747
• InChiKey: FVDMBIWLCHGEJI-SCXVOSTRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.19
• 重原子数：
  35
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (5S,6R)-3-hydroxymethyl-5-O-tert-butyl-diphenylsilyl-6,7-O-cyclohexylidene-5,6,7-trihydroxy-hept-1-ene 在 吡啶 、 4-二甲氨基吡啶 、 水 、 三乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 生成 [(4S,5R)-4-[tert-butyl(diphenyl)silyl]oxy-2-ethenyl-5,6-bis-(4-methylphenyl)sulfonyloxyhexyl] benzoate
  参考文献：
  名称：

  Stereodivergent Route to the Carbocyclic Core of 2′,3′-Olefinic Carbanucleosides: Toward the Synthesis of (l)-(+)- and (d)-(−)-Carbovir

  摘要：

  (R)-2,3-Cyclohexylideneglyceraldehyde (1) has been elegantly exploited for a stereodivergent construction of the potential precursors (ha and 11b) of (L)-(+)- and (D)-(-)-carbovirs, respectively. The key steps in this approach were Luche's allylation of formaldehyde with allylic bromide 4c to produce 5 and ring-closing metathesis of 10b using Grubbs' first-generation catalyst to obtain 11. The moderate stereoselectivity of Luche's allylation reaction resulted in attaining stereodivergence in this approach which could be realized finally through easy chromatographic separation of the two isomers of the metathesis product to obtain homochiral precursors ha and lib in good amounts.

  DOI：

  10.1021/jo200670v
• 作为产物：
  描述：

  (5S,6R)-ethyl-5-O-tert-butyl-diphenylsilyl-6,7-O-cyclohexylidene-5,6,7-trihydroxy-hept-2E-enoate 在 二异丁基氢化铝 、 碳酸氢钠 、 三乙胺 、 sodium bromide 、 锌 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 丙酮 为溶剂， 反应 2.67h， 生成 (5S,6R)-3-hydroxymethyl-5-O-tert-butyl-diphenylsilyl-6,7-O-cyclohexylidene-5,6,7-trihydroxy-hept-1-ene
  参考文献：
  名称：

  Stereodivergent Route to the Carbocyclic Core of 2′,3′-Olefinic Carbanucleosides: Toward the Synthesis of (l)-(+)- and (d)-(−)-Carbovir

  摘要：

  (R)-2,3-Cyclohexylideneglyceraldehyde (1) has been elegantly exploited for a stereodivergent construction of the potential precursors (ha and 11b) of (L)-(+)- and (D)-(-)-carbovirs, respectively. The key steps in this approach were Luche's allylation of formaldehyde with allylic bromide 4c to produce 5 and ring-closing metathesis of 10b using Grubbs' first-generation catalyst to obtain 11. The moderate stereoselectivity of Luche's allylation reaction resulted in attaining stereodivergence in this approach which could be realized finally through easy chromatographic separation of the two isomers of the metathesis product to obtain homochiral precursors ha and lib in good amounts.

  DOI：

  10.1021/jo200670v

文献信息

• Stereodivergent Route to the Carbocyclic Core of 2′,3′-Olefinic Carbanucleosides: Toward the Synthesis of (<scp>l</scp>)-(+)- and (<scp>d</scp>)-(−)-Carbovir
  作者：Angshuman Chattopadhyay、Sibanarayan Tripathy

  DOI：10.1021/jo200670v

  日期：2011.7.15

  (R)-2,3-Cyclohexylideneglyceraldehyde (1) has been elegantly exploited for a stereodivergent construction of the potential precursors (ha and 11b) of (L)-(+)- and (D)-(-)-carbovirs, respectively. The key steps in this approach were Luche's allylation of formaldehyde with allylic bromide 4c to produce 5 and ring-closing metathesis of 10b using Grubbs' first-generation catalyst to obtain 11. The moderate stereoselectivity of Luche's allylation reaction resulted in attaining stereodivergence in this approach which could be realized finally through easy chromatographic separation of the two isomers of the metathesis product to obtain homochiral precursors ha and lib in good amounts.