ethyl 5-(5'-amino-5'-deoxy-1',2'-O-isopropylidene-3'-O-methyl-α-D-xylofuranos-5'-yl)-6,7-dideoxy-1,2:3,4-di-O-isopropylidene-β-L-glycero-α-D-galactopyranuronate | 835617-70-4

• 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-5'-deoxy-1',2'-O-isopropylidene-3'-O-methyl-α-D-xylofuranos-5'-yl)-6,7-dideoxy-1,2:3,4-di-O-isopropylidene-β-L-glycero-α-D-galactopyranuronate
• 英文别名: ethyl (3S)-3-[[(3aR,5R,6S,6aR)-6-methoxy-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]methylamino]-3-[(1S,2R,6R,8R,9S)-4,4,11,11-tetramethyl-3,5,7,10,12-pentaoxatricyclo[7.3.0.02,6]dodecan-8-yl]propanoate
• CAS: 835617-70-4
• 化学式: C₂₅H₄₁NO₁₁
• 分子量: 531.601
• InChiKey: DJIBEDJFIAZWLI-KTGGXXNSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  37
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  121
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  ethyl 5-(5'-amino-5'-deoxy-1',2'-O-isopropylidene-3'-O-methyl-α-D-xylofuranos-5'-yl)-6,7-dideoxy-1,2:3,4-di-O-isopropylidene-β-L-glycero-α-D-galactopyranuronate 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 以55%的产率得到5-(5'-amino-5'-deoxy-1',2'-O-isopropylidene-3'-O-methyl-α-D-xylofuranos-5'-yl)-6,7-dideoxy-1,2:3,4-di-O-isopropylidene-β-L-glycero-α-D-galactoctanol
  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-5'-deoxy-1',2'-O-isopropylidene-3'-O-methyl-α-D-xylofuranos-5'-yl)-6,7-dideoxy-1,2:3,4-di-O-isopropylidene-β-L-glycero-α-D-galactopyranuronate
  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

文献信息

• Reductive Amination of Glycosyl Aldoses: Synthesis of<i>N</i>‐Glycosylated β‐Glycosyl Amino Alcohols and their Enzyme Inhibitory Effect
  作者：Shyam Sunder Verma、Ram Chandra Mishra、Akhilesh Kumar Tamarakar、Brajendra Kumar Tripathi、Arvind Kumar Srivastava、Rama Pati Tripathi

  DOI：10.1081/car-200046779

  日期：2004.1

  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.