methyl 6-[5a-carba-α-D-xylo-hex-5(5a)-enopyranosylamino]-6-deoxy-α-D-glucopyranoside | 1333121-74-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 6-[5a-carba-α-D-xylo-hex-5(5a)-enopyranosylamino]-6-deoxy-α-D-glucopyranoside
• 英文别名: (2S,3R,4S,5S,6R)-2-methoxy-6-[[[(1S,4R,5S,6S)-4,5,6-trihydroxy-3-(hydroxymethyl)cyclohex-2-en-1-yl]amino]methyl]oxane-3,4,5-triol
• CAS: 1333121-74-6
• 化学式: C₁₄H₂₅NO₉
• 分子量: 351.354
• InChiKey: UEQNOLBFMFPXCR-LXTFTDBNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.8
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  172
• 氢给体数：
  8
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  (1S,4R,5S,6S)-N-[[(2R,3R,4S,5R,6S)-6-methoxy-3,4,5-tris(phenylmethoxy)oxan-2-yl]methyl]-4,5,6-tris(phenylmethoxy)-3-(phenylmethoxymethyl)cyclohex-2-en-1-amine 在 氨 、 sodium 作用下， 以 四氢呋喃 为溶剂， 反应 0.33h， 以38%的产率得到methyl 6-[5a-carba-α-D-xylo-hex-5(5a)-enopyranosylamino]-6-deoxy-α-D-glucopyranoside
  参考文献：
  名称：

  Synthesis and α-Glucosidase II inhibitory activity of valienamine pseudodisaccharides relevant to N-glycan biosynthesis

  摘要：

  Valienol-derived allylic C-1 bromides have been used as carbaglycosyl donors for alpha-xylo configured valienamine pseudodisaccharide synthesis. We synthesised valienamine analogues of the Glc(alpha 1 -> 3)Glc and Glc(alpha 1 -> 3) Man disaccharides representing the linkages cleaved by alpha-Glucosidase II in N-glycan biosynthesis. These (N1 -> 3)-linked pseudodisaccharides were found to have some alpha-Glucosidase II inhibitory activity, while two other (N1 -> 6)-linked valienamine pseudodisaccharides failed to inhibit the enzyme. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.07.046

文献信息

• Synthesis and α-Glucosidase II inhibitory activity of valienamine pseudodisaccharides relevant to N-glycan biosynthesis
  作者：Ian Cumpstey、Clinton Ramstadius、K. Eszter Borbas、Dominic S. Alonzi、Terry D. Butters

  DOI：10.1016/j.bmcl.2011.07.046

  日期：2011.9

  Valienol-derived allylic C-1 bromides have been used as carbaglycosyl donors for alpha-xylo configured valienamine pseudodisaccharide synthesis. We synthesised valienamine analogues of the Glc(alpha 1 -> 3)Glc and Glc(alpha 1 -> 3) Man disaccharides representing the linkages cleaved by alpha-Glucosidase II in N-glycan biosynthesis. These (N1 -> 3)-linked pseudodisaccharides were found to have some alpha-Glucosidase II inhibitory activity, while two other (N1 -> 6)-linked valienamine pseudodisaccharides failed to inhibit the enzyme. (C) 2011 Elsevier Ltd. All rights reserved.