(1R,2'S,3'S,3R,4S,5R)-1-hydroxymethyl-3-O-tert-butyl(dimethyl)silyl-4-O,5-O-(2',3'-dimethoxybutane-2',3'-diyl)cyclohexane-1,3,4,5-tetraol | 213536-07-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1R,2'S,3'S,3R,4S,5R)-1-hydroxymethyl-3-O-tert-butyl(dimethyl)silyl-4-O,5-O-(2',3'-dimethoxybutane-2',3'-diyl)cyclohexane-1,3,4,5-tetraol
• 英文别名: (2S,3S,4aR,6R,8R,8aS)-8-[tert-butyl(dimethyl)silyl]oxy-6-(hydroxymethyl)-2,3-dimethoxy-2,3-dimethyl-5,7,8,8a-tetrahydro-4aH-benzo[b][1,4]dioxin-6-ol
• CAS: 213536-07-3
• 化学式: C₁₉H₃₈O₇Si
• 分子量: 406.592
• InChiKey: LFMGXODDDRDKGS-BLIIATGQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  86.6
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (1R,2'S,3'S,3R,4S,5R)-1-hydroxymethyl-3-O-tert-butyl(dimethyl)silyl-4-O,5-O-(2',3'-dimethoxybutane-2',3'-diyl)cyclohexane-1,3,4,5-tetraol 在 2,6-二甲基吡啶 、 sodium chlorite 、 2-甲基-2-丁烯 、 三丁基膦 、 间氯过氧苯甲酸 、 三氟乙酸 、 三氟乙酸酐 作用下， 以 四氢呋喃 、 水 、 叔丁醇 为溶剂， 生成 莽草酸
  参考文献：
  名称：

  Direct conversion of 1,2-diol into allyl sulfide. Regioselective transformation of (−)-quinic acid to (−)-shikimic acid

  摘要：

  Exo-1,2-diols 3 and 4 were efficiently converted into the corresponding allyl sulfides by means of tri-n-butylphosphine (Bu3P) and diphenyl disulfide (PhS)(2). This method was applied to the introduction of a carbon-carbon double bond from diol 11 to give allyl sulfide 12 in a highly regioselective manner. The allyl sulfide 12 was transformed into (-)-shikimic acid (1) in four steps. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)01239-8
• 作为产物：
  描述：

  (2'S,3'S)-methyl 3-O-tert-butyl(dimethyl)silyl-4-O,5-O-(2',3'-dimethoxybutane-2',3'-diyl)quinate 在 二异丁基氢化铝 作用下， 以 四氢呋喃 为溶剂， 以97%的产率得到(1R,2'S,3'S,3R,4S,5R)-1-hydroxymethyl-3-O-tert-butyl(dimethyl)silyl-4-O,5-O-(2',3'-dimethoxybutane-2',3'-diyl)cyclohexane-1,3,4,5-tetraol
  参考文献：
  名称：

  Direct conversion of 1,2-diol into allyl sulfide. Regioselective transformation of (−)-quinic acid to (−)-shikimic acid

  摘要：

  Exo-1,2-diols 3 and 4 were efficiently converted into the corresponding allyl sulfides by means of tri-n-butylphosphine (Bu3P) and diphenyl disulfide (PhS)(2). This method was applied to the introduction of a carbon-carbon double bond from diol 11 to give allyl sulfide 12 in a highly regioselective manner. The allyl sulfide 12 was transformed into (-)-shikimic acid (1) in four steps. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)01239-8

文献信息

• Difluorinated analogues of shikimic acid
  作者：Lovely Begum、Julian M Box、Michael G.B Drew、Laurence M Harwood、Jane L Humphreys、David J Lowes、Gareth A Morris、Perrine M Redon、Francine M Walker、Roger C Whitehead

  DOI：10.1016/s0040-4020(03)00697-5

  日期：2003.6

  Investigations into the quinate to shikimate transformation have been carried out, the results of which have been exploited in the synthesis of a novel difluoromethylene homologue of shikimic acid from (-)-quinic acid. Martin's sulfurane Ph2S[OC(CF3)(2)Ph](2)} was the reagent of choice for the key dehydration step of this synthesis. The results of investigations into the synthesis of the important natural product analogue, 6,6-difluoroshikimic acid are also reported. (C) 2003 Elsevier Science Ltd. All rights reserved.