methyl 6-O-formyl-α-D-glucopyranoside | 131021-83-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 6-O-formyl-α-D-glucopyranoside
• 英文别名: [(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-methoxyoxan-2-yl]methyl formate
• CAS: 131021-83-5
• 化学式: C₈H₁₄O₇
• 分子量: 222.195
• InChiKey: GFWZOGBMOPJNHU-CBQIKETKSA-N

物化性质

• 沸点：
  391.1±42.0 °C(Predicted)
• 密度：
  1.44±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  105
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl 6-O-formyl-α-D-glucopyranoside 在 吡啶 、 盐酸 作用下， 以 甲醇 为溶剂， 反应 29.0h， 生成 甲基2,3,4-三-O-苯甲酰-α-D-吡喃葡萄糖苷
  参考文献：
  名称：

  Formylation of primary hydroxyl groups in sugars

  摘要：

  Application of 99% formic acid at 25 degrees formylates primary hydroxyl groups as shown by the easy formation of 6-O-formyl-D-glucopyranose and 6-O-formyl-D-fructofuranose, isolated as their tetra-acetates in yields of 77% and 31%, respectively. Likewise, D-glucitol gave the 2,3,4,5-tetra-O-acetyl-1,6-di-O-formyl derivative (84%) and methyl alpha-D-glucopyranoside gave the 6-formate (74%) characterized as the crystalline triacetate. On storage of the triacetate in methanol at 25 degrees, the formyl group was lost and the 2,3,6-triacetate was formed, whereas the corresponding tribenzoate was deformylated in acidic methanol without migration of the benzoyl groups.

  DOI：

  10.1016/0008-6215(90)84006-g
• 作为产物：
  描述：

  甲酸 、 alpha-甲基葡萄糖甙 反应 3.0h， 以74%的产率得到methyl 6-O-formyl-α-D-glucopyranoside
  参考文献：
  名称：

  Formylation of primary hydroxyl groups in sugars

  摘要：

  Application of 99% formic acid at 25 degrees formylates primary hydroxyl groups as shown by the easy formation of 6-O-formyl-D-glucopyranose and 6-O-formyl-D-fructofuranose, isolated as their tetra-acetates in yields of 77% and 31%, respectively. Likewise, D-glucitol gave the 2,3,4,5-tetra-O-acetyl-1,6-di-O-formyl derivative (84%) and methyl alpha-D-glucopyranoside gave the 6-formate (74%) characterized as the crystalline triacetate. On storage of the triacetate in methanol at 25 degrees, the formyl group was lost and the 2,3,6-triacetate was formed, whereas the corresponding tribenzoate was deformylated in acidic methanol without migration of the benzoyl groups.

  DOI：

  10.1016/0008-6215(90)84006-g

文献信息

• Mild and Highly Selective Formyl Protection of Primary Hydroxyl Groups
  作者：Lidia De Luca、Giampaolo Giacomelli、Andrea Porcheddu

  DOI：10.1021/jo0257492

  日期：2002.7.1

  Efficient conversion of primary alcohols to the corresponding formate esters can be carried out at room temperature in methylene chloride, using 2,4,6-trichloro-1,3,5-triazine and N,N-dimethylformamide in the presence of lithium fluoride. This procedure appears as a valid method for selectively protecting primary hydroxyl groups.

  可以在室温下在二氯甲烷中，在氟化锂的存在下，使用2,4,6-三氯-1,3,5-三嗪和N，N-二甲基甲酰胺在二氯甲烷中将伯醇有效转化为相应的甲酸酯。该程序似乎是选择性保护伯羟基的有效方法。
• GAN, LI-XIAN;WHISTLER, ROY L., CARBOHYDR. RES., 206,(1990) N, C. 65-69
  作者：GAN, LI-XIAN、WHISTLER, ROY L.

  DOI：——

  日期：——
• Formylation of primary hydroxyl groups in sugars
  作者：Li-Xian Gan、Roy L. Whistler

  DOI：10.1016/0008-6215(90)84006-g

  日期：1990.9

  Application of 99% formic acid at 25 degrees formylates primary hydroxyl groups as shown by the easy formation of 6-O-formyl-D-glucopyranose and 6-O-formyl-D-fructofuranose, isolated as their tetra-acetates in yields of 77% and 31%, respectively. Likewise, D-glucitol gave the 2,3,4,5-tetra-O-acetyl-1,6-di-O-formyl derivative (84%) and methyl alpha-D-glucopyranoside gave the 6-formate (74%) characterized as the crystalline triacetate. On storage of the triacetate in methanol at 25 degrees, the formyl group was lost and the 2,3,6-triacetate was formed, whereas the corresponding tribenzoate was deformylated in acidic methanol without migration of the benzoyl groups.