(1S,2R)-2-<(tert-Butoxycarbonyl)amino>-3-hydroxy-2-N,3-O-isopropylidene-1-(1,3-thiazol-2-yl)-1-propanol | 145532-48-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (1S,2R)-2-<(tert-Butoxycarbonyl)amino>-3-hydroxy-2-N,3-O-isopropylidene-1-(1,3-thiazol-2-yl)-1-propanol
• 英文别名: tert-butyl (4R)-4-[(S)-hydroxy(1,3-thiazol-2-yl)methyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate
• CAS: 145532-48-5
• 化学式: C₁₄H₂₂N₂O₄S
• 分子量: 314.406
• InChiKey: DZPVRXJJHOGXCG-ZJUUUORDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  100
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (1S,2R)-2-<(tert-Butoxycarbonyl)amino>-3-hydroxy-2-N,3-O-isopropylidene-1-(1,3-thiazol-2-yl)-1-propanol 在 叔丁基过氧化氢 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 四氧化锇 、 4 A molecular sieve 、 水 、 4-甲基苯磺酸吡啶 、 N-甲基吗啉氧化物 、 三乙胺 、 mercury dichloride 作用下， 以 N,N-二甲基甲酰胺 、 丙酮 、 甲苯 、 乙腈 、 叔丁醇 为溶剂， 反应 46.83h， 生成 (1R,2S,3S,4R)-4-<(tert-Butoxycarbonyl)amino>-3-<(tert-butyldimethylsilyl)oxy>-1,2-(isopropylidenedioxy)-5-hydroxy-4-N,5-O-isopropylidene-1-(1,3-thiazol-2-yl)pentane
  参考文献：
  名称：

  Total Synthesis of (+)-Galactostatin. An Illustration of the Utility of the Thiazole-Aldehyde Synthesis

  摘要：

  The natural aza sugar (+)-galactostatin (+)-1 has been prepared from D-serine by sequential installation of chiral 1C and 2C units employing thiazole-based reagents. Thus, the D-serine-derived methyl ester 3 was transformed by 2-thiazolyllithium (4) into the thiazolyl amino ketone 5 which, via syn stereoselective carbonyl reduction and thiazolyl-to-formyl conversion, gave the first key intermediate, the alpha-hydroxy beta-amino aldehyde 10. The olefination of this compound by [(2-thiazolyl)-methylene]triphenylphosphorane (14) followed by osmium tetroxide cis dihydroxylation of the resulting alkene E-16 and cleavage of the thiazole ring produced the second key intermediate, the amino- and hydroxyl-protected 5-deoxy-5-amino- D-galactose 20. The removal of all protecting groups of this compound afforded the target aza sugar (+)-1 in 17.3% overall yield from 3.

  DOI：

  10.1021/jo00120a017
• 作为产物：
  描述：

  (R)-2-<(tert-Butoxycarbonyl)amino>-3-hydroxy-2-N,3-O-isopropylidene-1-(1,3-thiazol-2-yl)-1-propanone 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成 (1S,2R)-2-<(tert-Butoxycarbonyl)amino>-3-hydroxy-2-N,3-O-isopropylidene-1-(1,3-thiazol-2-yl)-1-propanol
  参考文献：
  名称：

  Stereocontrolled total synthesis of galactostatin from serine

  摘要：

  介绍了通过噻唑中间体作为受保护的醛，从 N-叔丁氧羰基-2,3-异亚丙基 L-丝氨酸甲酯高效立体选择性全合成 (-)-galactostatin (-)-1（总收率 21%）的方法；从 D-丝氨酸开始平行合成天然反极 (+)-1。

  DOI：

  10.1039/c39910001576

文献信息

• Efficacious modification of the procedure for the aldehyde release from 2-substituted thiazoles
  作者：Alessandro Dondoni、Alberto Marra、Daniela Perrone

  DOI：10.1021/jo00053a055

  日期：1993.1
• Stereocontrolled total synthesis of galactostatin from serine
  作者：Alessandro Dondoni、Pedro Merino、Daniela Perrone

  DOI：10.1039/c39910001576

  日期：——

  An efficient stereoselective total synthesis of (–)-galactostatin (–)-1 from N-tert-butoxycarbonyi-2,3-isopropylidene L-serine methyl ester (21% overall yield) is described via thiazole intermediates serving as protected aldehydes; the parallel synthesis of the natural antipole (+)-1 starts from D-serine.

  介绍了通过噻唑中间体作为受保护的醛，从 N-叔丁氧羰基-2,3-异亚丙基 L-丝氨酸甲酯高效立体选择性全合成 (-)-galactostatin (-)-1（总收率 21%）的方法；从 D-丝氨酸开始平行合成天然反极 (+)-1。
• Total Synthesis of (+)-Galactostatin. An Illustration of the Utility of the Thiazole-Aldehyde Synthesis
  作者：Alessandro Dondoni、Daniela Perrone

  DOI：10.1021/jo00120a017

  日期：1995.7

  The natural aza sugar (+)-galactostatin (+)-1 has been prepared from D-serine by sequential installation of chiral 1C and 2C units employing thiazole-based reagents. Thus, the D-serine-derived methyl ester 3 was transformed by 2-thiazolyllithium (4) into the thiazolyl amino ketone 5 which, via syn stereoselective carbonyl reduction and thiazolyl-to-formyl conversion, gave the first key intermediate, the alpha-hydroxy beta-amino aldehyde 10. The olefination of this compound by [(2-thiazolyl)-methylene]triphenylphosphorane (14) followed by osmium tetroxide cis dihydroxylation of the resulting alkene E-16 and cleavage of the thiazole ring produced the second key intermediate, the amino- and hydroxyl-protected 5-deoxy-5-amino- D-galactose 20. The removal of all protecting groups of this compound afforded the target aza sugar (+)-1 in 17.3% overall yield from 3.