ethyl 5-(5'-amino-3'-5'-deoxy-1',2'-O-isopropylidene-3'-O-methyla-D-xylofuranos-5'-yl)-3-O-allyl-5,6-dideoxy-1,2-O-isopropylidene-β-L-ido-heptafuranuronate | 835617-68-0

• 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-(5'-amino-3'-5'-deoxy-1',2'-O-isopropylidene-3'-O-methyla-D-xylofuranos-5'-yl)-3-O-allyl-5,6-dideoxy-1,2-O-isopropylidene-β-L-ido-heptafuranuronate
• CAS: 835617-68-0
• 化学式: C₂₄H₃₉NO₁₀
• 分子量: 501.574
• InChiKey: FUKLELIEGKLKDD-ZENJJLATSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.24
• 重原子数：
  35.0
• 可旋转键数：
  11.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.88
• 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-(5'-amino-3'-5'-deoxy-1',2'-O-isopropylidene-3'-O-methyla-D-xylofuranos-5'-yl)-3-O-allyl-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70%的产率得到5-(5'-amino-3'-5'-deoxy-1',2'-O-isopropylidene-3'-O-methyla-D-xylofuranos-5'-yl)-3-O-allyl-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：

  1,2-O-异亚丙基-3-O-甲基-Alpha-D-木五二呋喃醛糖-(1,4) 在 sodium tetrahydroborate 作用下， 以 甲醇 、 氯仿 为溶剂， 生成 ethyl 5-(5'-amino-3'-5'-deoxy-1',2'-O-isopropylidene-3'-O-methyla-D-xylofuranos-5'-yl)-3-O-allyl-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