3-<(tert-Butoxycarbonyl)amino>-2-O-(tert-butyldimethylsilyl)-3-deoxy-3-N,4-O-isopropylidene-D-threose | 168326-01-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: 3-<(tert-Butoxycarbonyl)amino>-2-O-(tert-butyldimethylsilyl)-3-deoxy-3-N,4-O-isopropylidene-D-threose
• 英文别名: tert-butyl (4R)-4-[(1S)-1-[tert-butyl(dimethyl)silyl]oxy-2-oxoethyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate
• CAS: 168326-01-0
• 化学式: C₁₈H₃₅NO₅Si
• 分子量: 373.565
• InChiKey: LJVXWIQSYMKZDP-ZIAGYGMSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.95
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  65.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-<(tert-Butoxycarbonyl)amino>-2-O-(tert-butyldimethylsilyl)-3-deoxy-3-N,4-O-isopropylidene-D-threose 在 叔丁基过氧化氢 、 四氧化锇 、 水 、 4-甲基苯磺酸吡啶 、 N-甲基吗啉氧化物 作用下， 以 丙酮 、 甲苯 、 叔丁醇 为溶剂， 反应 45.0h， 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：

  (1S,2S)-2-<(tert-Butoxycarbonyl)amino>-<(1-tert-butyldimethylsilyl)oxy>-3-hydroxy-2-N,3-O-isopropylidene-1-(1,3-thiazol-2-yl)propane 在 sodium tetrahydroborate 、 4 A molecular sieve 、 mercury dichloride 作用下， 以 乙腈 为溶剂， 反应 0.83h， 生成 3-<(tert-Butoxycarbonyl)amino>-2-O-(tert-butyldimethylsilyl)-3-deoxy-3-N,4-O-isopropylidene-D-threose
  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

文献信息

• 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.