tert-butyl (+)-(3R,4S)-3,4-dihydroxy-4-(2-thiazolyl)-butanoate | 244217-24-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: tert-butyl (+)-(3R,4S)-3,4-dihydroxy-4-(2-thiazolyl)-butanoate
• 英文别名: tert-butyl (3R,4S)-3,4-dihydroxy-4-(1,3-thiazol-2-yl)butanoate
• CAS: 244217-24-1
• 化学式: C₁₁H₁₇NO₄S
• 分子量: 259.326
• InChiKey: JZCGIHMEDWRSAT-APPZFPTMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  108
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  tert-butyl (+)-(3R,4S)-3,4-dihydroxy-4-(2-thiazolyl)-butanoate 在 sodium tetrahydroborate 、 molecular sieve 、 sodium hydride 、 对甲苯磺酸 、 三氟甲烷磺酸甲酯 作用下， 以 甲醇 、 乙二醇二甲醚 、 丙酮 、 乙腈 为溶剂， 反应 4.5h， 生成 tert-butyl (+)-(3S,5R,7S,10R,11R)-1-tert-butyldimethylsilyloxy-7-hydroxy-3,5:10,11-di(isopropylidenedioxy)-tridec-8-en-13-oate
  参考文献：
  名称：

  First Stereocontrolled Synthesis of the (3S,5R,7R,10R,11R)-C1−C13 Fragment of Nystatin A₁

  摘要：

  A convergent stereoselective synthesis of the (3S,5R,7R,10R,11R)-C1-C13 fragment of Nystatin Al is reported in this paper. This fragment contains an all-syn-1,3,5-triol subunit and a syn-1,2-diol moiety. The main features of the synthesis are the enzymatic desymmetrization of a meso diol to obtain an enantiomerically pure syn-4,6-dihydroxy-2-keto-phosphonate, chiral sulfoxide chemistry to prepare an alpha-(R)-hydroxyaldehyde and 2-trimethylsilyl thiazole reagent to synthesize a synthesize a syn-alpha,beta-(R,S)-dihydroxy aldehyde.

  DOI：

  10.1021/jo990245y
• 作为产物：
  描述：

  tert-butyl (3R)-3-tert-butyldimethylsilyloxy-4-acetoxy-4-p-tolylsulfenyl-butanoate 在 草酰氯 、 四丁基氟化铵 、 镍 、 二异丁基氢化铝 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 6.3h， 生成 tert-butyl (+)-(3R,4S)-3,4-dihydroxy-4-(2-thiazolyl)-butanoate
  参考文献：
  名称：

  First Stereocontrolled Synthesis of the (3S,5R,7R,10R,11R)-C1−C13 Fragment of Nystatin A₁

  摘要：

  A convergent stereoselective synthesis of the (3S,5R,7R,10R,11R)-C1-C13 fragment of Nystatin Al is reported in this paper. This fragment contains an all-syn-1,3,5-triol subunit and a syn-1,2-diol moiety. The main features of the synthesis are the enzymatic desymmetrization of a meso diol to obtain an enantiomerically pure syn-4,6-dihydroxy-2-keto-phosphonate, chiral sulfoxide chemistry to prepare an alpha-(R)-hydroxyaldehyde and 2-trimethylsilyl thiazole reagent to synthesize a synthesize a syn-alpha,beta-(R,S)-dihydroxy aldehyde.

  DOI：

  10.1021/jo990245y

文献信息

• First Stereocontrolled Synthesis of the (3<i>S</i>,5<i>R</i>,7<i>R</i>,10<i>R</i>,11<i>R</i>)-C1−C13 Fragment of Nystatin A₁
  作者：Guy Solladié、Nicole Wilb、Claude Bauder、Carlo Bonini、Licia Viggiani、Lucia Chiummiento

  DOI：10.1021/jo990245y

  日期：1999.7.1

  A convergent stereoselective synthesis of the (3S,5R,7R,10R,11R)-C1-C13 fragment of Nystatin Al is reported in this paper. This fragment contains an all-syn-1,3,5-triol subunit and a syn-1,2-diol moiety. The main features of the synthesis are the enzymatic desymmetrization of a meso diol to obtain an enantiomerically pure syn-4,6-dihydroxy-2-keto-phosphonate, chiral sulfoxide chemistry to prepare an alpha-(R)-hydroxyaldehyde and 2-trimethylsilyl thiazole reagent to synthesize a synthesize a syn-alpha,beta-(R,S)-dihydroxy aldehyde.