2-(2,3:5,6-Di-O-isopropylidene-β-D-mannofuranosyl)thiazole | 154127-60-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(2,3:5,6-Di-O-isopropylidene-β-D-mannofuranosyl)thiazole
• 英文别名: 2-[(3aS,4R,6R,6aS)-6-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-1,3-thiazole
• CAS: 154127-60-3
• 化学式: C₁₅H₂₁NO₅S
• 分子量: 327.401
• InChiKey: BJIFCANZUBNGKQ-LDMBFOFVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  87.3
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-(2,3:5,6-Di-O-isopropylidene-β-D-mannofuranosyl)thiazole 在 sodium tetrahydroborate 、 三氟甲烷磺酸甲酯 、 mercury dichloride 作用下， 生成 formyl C-mannofuranoside diacetonide
  参考文献：
  名称：

  Thiazole-based synthesis of C-glycosyl aldehydes

  摘要：

  The formylation at the anomeric carbon of the model sugars 2,3,4,6-tetra-O-benzyl-D-glucopyranose and 2,3:5,6-di-O-isopropylidene-D-mannofuranose is carried out by addition of 2-lithiothiazole to the corresponding lactones followed by reductive dehydroxylation and thiazole to formyl deblocking.

  DOI：

  10.1016/s0040-4039(00)79319-1
• 作为产物：
  描述：

  2,3:5,6-二-O-异亚丙基-D-甘露糖酸-1,4-内酯 在 三乙基硅烷 、 正丁基锂 、 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 、 三乙胺 作用下， 以 乙醚 、 正己烷 、 二氯甲烷 为溶剂， 反应 1.67h， 生成 2-(2,3:5,6-Di-O-isopropylidene-β-D-mannofuranosyl)thiazole
  参考文献：
  名称：

  Thiazole-Based Synthesis of Formyl C-Glycosides

  摘要：

  A method for the installation of the formyl group at the anomeric position of pyranoses and furanoses starting from the corresponding lactones has been developed. The strategy involves the addition of 2-lithiothiazole to the sugar lactone, followed by the silane reduction of the acetylated resultant ketol and the unmasking of the formyl group from the thiazole ring. All steps have been studied in some details to improve chemical efficiency and stereochemical control. Hence, reversed alpha:beta ratios of ketols were found in kinetic and thermodynamic mixtures, the former being consistent with a steric effect control of the substituents and the latter by the electronic effect of the ring oxygen. Seven sugar aldehydes with different D-pyranosidic (2,3,4,6-tetra-O-benzyl-gluco, -galacto, and -manno, 2-azido-3,4,6-tri-O-benzyl-2-deoxy-galacto) and D-furanosidic moieties (5-O-benzyl-2,3-isopropylidene-ribo; 2,3,5-tri-O-benzyl-ribo; 2,3:5,6-di-O-isopropylidene-manno) were prepared in 52-65% isolated overall yield from the corresponding lactone.

  DOI：

  10.1021/jo00100a050

文献信息

• Thiazole-Based Synthesis of Formyl C-Glycosides
  作者：Alessandro Dondoni、Marie-Christine Scherrmann

  DOI：10.1021/jo00100a050

  日期：1994.10

  A method for the installation of the formyl group at the anomeric position of pyranoses and furanoses starting from the corresponding lactones has been developed. The strategy involves the addition of 2-lithiothiazole to the sugar lactone, followed by the silane reduction of the acetylated resultant ketol and the unmasking of the formyl group from the thiazole ring. All steps have been studied in some details to improve chemical efficiency and stereochemical control. Hence, reversed alpha:beta ratios of ketols were found in kinetic and thermodynamic mixtures, the former being consistent with a steric effect control of the substituents and the latter by the electronic effect of the ring oxygen. Seven sugar aldehydes with different D-pyranosidic (2,3,4,6-tetra-O-benzyl-gluco, -galacto, and -manno, 2-azido-3,4,6-tri-O-benzyl-2-deoxy-galacto) and D-furanosidic moieties (5-O-benzyl-2,3-isopropylidene-ribo; 2,3,5-tri-O-benzyl-ribo; 2,3:5,6-di-O-isopropylidene-manno) were prepared in 52-65% isolated overall yield from the corresponding lactone.
• Thiazole-based synthesis of C-glycosyl aldehydes
  作者：Alessandro Dondoni、Marie-Christine Scherrmann

  DOI：10.1016/s0040-4039(00)79319-1

  日期：1993.11

  The formylation at the anomeric carbon of the model sugars 2,3,4,6-tetra-O-benzyl-D-glucopyranose and 2,3:5,6-di-O-isopropylidene-D-mannofuranose is carried out by addition of 2-lithiothiazole to the corresponding lactones followed by reductive dehydroxylation and thiazole to formyl deblocking.