2-O-Benzyl-3-<(tert-butoxycarbonyl)amino>-3-deoxy-3-N,4-O-isopropylidene-D-threose | 145532-44-1

• 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: 2-O-Benzyl-3-<(tert-butoxycarbonyl)amino>-3-deoxy-3-N,4-O-isopropylidene-D-threose
• 英文别名: 2-O-benzyl-3-<(tert-butoxycarbonyl)amino>-3-deoxy-3,4-N,O-isopropylidene-D-threose；2-O-benzyl-3-[(tert-butoxycarbonyl)amino]-3-deoxy-3,4-N,O-isopropylidene-D-threose；tert-butyl (4R)-2,2-dimethyl-4-[(1S)-2-oxo-1-phenylmethoxyethyl]-1,3-oxazolidine-3-carboxylate
• CAS: 145532-44-1
• 化学式: C₁₉H₂₇NO₅
• 分子量: 349.427
• InChiKey: PFNMEVNERFMVHP-HZPDHXFCSA-N

物化性质

• 沸点：
  435.3±40.0 °C(predicted)
• 密度：
  1.116±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 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：

  2-thiazolylmethylenetriphenylphosphorane 、 2-O-Benzyl-3-<(tert-butoxycarbonyl)amino>-3-deoxy-3-N,4-O-isopropylidene-D-threose 以 甲苯 为溶剂， 反应 24.0h， 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 、 (R,R)-3-(Benzyloxy)-4-<(tert-butoxycarbonyl)amino>-5-hydroxy-4-N,5-O-isopropylidene-1-(1,3-thiazol-2-yl)-1(E)-pentene 、 (3S,4R)-3-(Benzyloxy)-4-<(tert-butoxycarbonyl)amino>-5-hydroxy-4-N,5-O-isopropylidene-1-(1,3-thiazol-2-yl)-1(Z)-pentene 、 (3S,4R)-3-(Benzyloxy)-4-<(tert-butoxycarbonyl)amino>-5-hydroxy-4-N,5-O-isopropylidene-1-(1,3-thiazol-2-yl)-1(E)-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：

  (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 乙腈 为溶剂， 反应 0.83h， 生成 2-O-Benzyl-3-<(tert-butoxycarbonyl)amino>-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

• 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.