2-(2,3,4,6-tetra-O-benzyl-β-D-mannopyranosyl)prop-2-enal | 1192714-01-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(2,3,4,6-tetra-O-benzyl-β-D-mannopyranosyl)prop-2-enal
• 英文别名: 2-[(2S,3R,4R,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]prop-2-enal
• CAS: 1192714-01-4
• 化学式: C₃₇H₃₈O₆
• 分子量: 578.705
• InChiKey: VBENULGAVLQPFQ-ORIAJCIFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  43
• 可旋转键数：
  15
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-(2,3,4,6-tetra-O-benzyl-β-D-mannopyranosyl)prop-2-enal 在 sodium chlorite 、 sodium dihydrogenphosphate 、 2-甲基-2-丁烯 、 盐酸 作用下， 以 水 、 叔丁醇 为溶剂， 生成
  参考文献：
  名称：

  Domino Heck/Lactonization-Catalyzed Synthesis of 3-C-Linked Mannopyranosyl Coumarins

  摘要：

  Selective syntheses of methyl alpha- (8) and beta-C-mannopyranosyl acrylates (9) were obtained from alpha-C-allyl mannopyranoside (3) by ozonolysis to 4 followed by alpha-methylenation to provide intermediate aldehydes 5 and 6. The beta-anomer 6 was obtained by in situ anomeric epimerization. The acrylates and the homologous alpha-anomer 16, obtained by oxidative hydroboration, oxidation, and alpha-methylenation, were converted into 3-C-linked mannopyranosyl coumarins 11, 12,and 19 in good yields under one-pot Heck/lactonization conditions.

  DOI：

  10.1021/jo901855p
• 作为产物：
  描述：

  聚合甲醛 、 2-(2,3,4,6-tetra-O-benzyl-β-D-mannopyranosyl)acetaldehyde 在 四氢吡咯 、 丙酸 作用下， 以 水 、 异丙醇 为溶剂， 以71%的产率得到2-(2,3,4,6-tetra-O-benzyl-β-D-mannopyranosyl)prop-2-enal
  参考文献：
  名称：

  Domino Heck/Lactonization-Catalyzed Synthesis of 3-C-Linked Mannopyranosyl Coumarins

  摘要：

  Selective syntheses of methyl alpha- (8) and beta-C-mannopyranosyl acrylates (9) were obtained from alpha-C-allyl mannopyranoside (3) by ozonolysis to 4 followed by alpha-methylenation to provide intermediate aldehydes 5 and 6. The beta-anomer 6 was obtained by in situ anomeric epimerization. The acrylates and the homologous alpha-anomer 16, obtained by oxidative hydroboration, oxidation, and alpha-methylenation, were converted into 3-C-linked mannopyranosyl coumarins 11, 12,and 19 in good yields under one-pot Heck/lactonization conditions.

  DOI：

  10.1021/jo901855p

文献信息

• Domino Heck/Lactonization-Catalyzed Synthesis of 3-<i>C</i>-Linked Mannopyranosyl Coumarins
  作者：Denis Giguère、Philipe Cloutier、René Roy

  DOI：10.1021/jo901855p

  日期：2009.11.6

  Selective syntheses of methyl alpha- (8) and beta-C-mannopyranosyl acrylates (9) were obtained from alpha-C-allyl mannopyranoside (3) by ozonolysis to 4 followed by alpha-methylenation to provide intermediate aldehydes 5 and 6. The beta-anomer 6 was obtained by in situ anomeric epimerization. The acrylates and the homologous alpha-anomer 16, obtained by oxidative hydroboration, oxidation, and alpha-methylenation, were converted into 3-C-linked mannopyranosyl coumarins 11, 12,and 19 in good yields under one-pot Heck/lactonization conditions.