(1S,2R)-1-(Benzyloxy)-2-<(tert-butoxycarbonyl)amino>-3-hydroxy-2-N,3-O-isopropylidene-1-(1,3-thiazol-2-yl)propane | 145532-49-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (1S,2R)-1-(Benzyloxy)-2-<(tert-butoxycarbonyl)amino>-3-hydroxy-2-N,3-O-isopropylidene-1-(1,3-thiazol-2-yl)propane
• 英文别名: (1S,2R)-1-O-benzyl-2-<(tert-butoxycarbonyl)amino>-2,3-N,O-isopropylidene-1-(2-thiazolyl)-1,3-propanediol；(1S,2R)-1-O-benzyl-2-[(tert-butoxycarbonyl)amino]-2,3-N,O-isopropylidene-1-(2-thiazolyl)-1,3-propanediol；tert-butyl (4R)-2,2-dimethyl-4-[(S)-phenylmethoxy(1,3-thiazol-2-yl)methyl]-1,3-oxazolidine-3-carboxylate
• CAS: 145532-49-6
• 化学式: C₂₁H₂₈N₂O₄S
• 分子量: 404.53
• InChiKey: BYUSQAJEEUAWAC-SJORKVTESA-N

物化性质

• 沸点：
  489.8±45.0 °C(predicted)
• 密度：
  1.183±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  89.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (1S,2R)-1-(Benzyloxy)-2-<(tert-butoxycarbonyl)amino>-3-hydroxy-2-N,3-O-isopropylidene-1-(1,3-thiazol-2-yl)propane 在 sodium tetrahydroborate 、 4 A molecular sieve 、 copper(II) oxide 、 copper dichloride 作用下， 以 甲苯 、 乙腈 为溶剂， 反应 24.83h， 生成 (R,R)-3-(Benzyloxy)-4-<(tert-butoxycarbonyl)amino>-5-hydroxy-4-N,5-O-isopropylidene-1-(1,3-thiazol-2-yl)-1(Z)-pentene
  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)-(+)-3-叔丁氧羰基-2,2-二甲基-4-噁唑烷羧酸甲 在 sodium tetrahydroborate 、 正丁基锂 、 sodium hydride 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.58h， 生成 (1S,2R)-1-(Benzyloxy)-2-<(tert-butoxycarbonyl)amino>-3-hydroxy-2-N,3-O-isopropylidene-1-(1,3-thiazol-2-yl)propane
  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

• 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
• 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.