ethyl 5-(3'-O-allyl-5'-amino-5'-deoxy-1',2'-O-isopropylidene-α-D-xylofuranos-5'-yl)-3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-β-L-ido-heptafuranuronate | 835617-64-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: ethyl 5-(3'-O-allyl-5'-amino-5'-deoxy-1',2'-O-isopropylidene-α-D-xylofuranos-5'-yl)-3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-β-L-ido-heptafuranuronate
• CAS: 835617-64-6
• 化学式: C₃₀H₄₃NO₁₀
• 分子量: 577.672
• InChiKey: JZCRHVQMCJXYPZ-DRVFMUMFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.81
• 重原子数：
  41.0
• 可旋转键数：
  13.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  112.17
• 氢给体数：
  1.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  ethyl 5-(3'-O-allyl-5'-amino-5'-deoxy-1',2'-O-isopropylidene-α-D-xylofuranos-5'-yl)-3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-β-L-ido-heptafuranuronate 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 以60%的产率得到5-(3'-O-allyl-5'-amino-5'-deoxy-1',2'-O-isopropylidene-α-D-xylofuranos-5'-yl)-3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-β-L-ido-heptanol
  参考文献：
  名称：

  Reductive Amination of Glycosyl Aldoses: Synthesis ofN‐Glycosylated β‐Glycosyl Amino Alcohols and their Enzyme Inhibitory Effect

  摘要：

  Reductive amination of glycosyl aldehydes (la-c, 2) with glycosyl amino esters (3a-c, 4) in the presence of sodium borohydride gave diglycosylated amino esters (5-15) in good yield. N-Glycosyl-glycosylated amino esters were reduced to the respective diglycosyl amino alcohols (16-26) with LiAlH4 in good yield. All the synthesized compounds were studied for their inhibitory effect, if any, against hepatic glucose-6-phosphatase, glycogen phosphorylase, and intestinal brush border membrane alpha-glucosidase; among these compounds 7, 21, and 25 have shown marked inhibition on these enzymes, respectively.

  DOI：

  10.1081/car-200046779
• 作为产物：
  描述：

  3-O-Allyl-1,2-O-isopropylidene-α-D-xylo-pentodialdose 在 sodium tetrahydroborate 作用下， 以 甲醇 、 氯仿 为溶剂， 生成 ethyl 5-(3'-O-allyl-5'-amino-5'-deoxy-1',2'-O-isopropylidene-α-D-xylofuranos-5'-yl)-3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-β-L-ido-heptafuranuronate
  参考文献：
  名称：

  Reductive Amination of Glycosyl Aldoses: Synthesis ofN‐Glycosylated β‐Glycosyl Amino Alcohols and their Enzyme Inhibitory Effect

  摘要：

  Reductive amination of glycosyl aldehydes (la-c, 2) with glycosyl amino esters (3a-c, 4) in the presence of sodium borohydride gave diglycosylated amino esters (5-15) in good yield. N-Glycosyl-glycosylated amino esters were reduced to the respective diglycosyl amino alcohols (16-26) with LiAlH4 in good yield. All the synthesized compounds were studied for their inhibitory effect, if any, against hepatic glucose-6-phosphatase, glycogen phosphorylase, and intestinal brush border membrane alpha-glucosidase; among these compounds 7, 21, and 25 have shown marked inhibition on these enzymes, respectively.

  DOI：

  10.1081/car-200046779