5-<(tert-Butoxycarbonyl)amino>-4-O-(tert-butyldimethylsilyl)-5-deoxy-2-O,3-O-isopropylidene-5-N,6-O-isopropylidene-D-galactose | 168326-10-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-<(tert-Butoxycarbonyl)amino>-4-O-(tert-butyldimethylsilyl)-5-deoxy-2-O,3-O-isopropylidene-5-N,6-O-isopropylidene-D-galactose
• 英文别名: tert-butyl (4R)-4-[(S)-[tert-butyl(dimethyl)silyl]oxy-[(4R,5R)-5-formyl-2,2-dimethyl-1,3-dioxolan-4-yl]methyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate
• CAS: 168326-10-1
• 化学式: C₂₃H₄₃NO₇Si
• 分子量: 473.682
• InChiKey: UJLCHCHTBJLUJT-VSZNYVQBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.47
• 重原子数：
  32
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  83.5
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  5-<(tert-Butoxycarbonyl)amino>-4-O-(tert-butyldimethylsilyl)-5-deoxy-2-O,3-O-isopropylidene-5-N,6-O-isopropylidene-D-galactose 在 二氧化硫 、 水 作用下， 以67%的产率得到5-amino-5-deoxy-D-galactopyranose hydrogensulfite adduct
  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：

  (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 在 sodium tetrahydroborate 、 4 A molecular sieve 、 mercury dichloride 作用下， 以 乙腈 为溶剂， 反应 0.83h， 生成 5-<(tert-Butoxycarbonyl)amino>-4-O-(tert-butyldimethylsilyl)-5-deoxy-2-O,3-O-isopropylidene-5-N,6-O-isopropylidene-D-galactose
  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.