8-methoxycarbonyloctyl O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside | 90405-12-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 8-methoxycarbonyloctyl O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside
• 英文别名: 8-Methoxycarbonyloct-1-yl O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1-4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside；8-methoxycarbonyloctyl 2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-glucopyranoside；methyl 9-[(2R,3R,4S,5R,6R)-3,4-diacetyloxy-6-(acetyloxymethyl)-5-[(2S,3R,4S,5S,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyoxan-2-yl]oxynonanoate
• CAS: 90405-12-2
• 化学式: C₃₆H₅₄O₂₀
• 分子量: 806.813
• InChiKey: UTXKJAGZTXGWNS-FVUSEMRQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  56
• 可旋转键数：
  29
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  247
• 氢给体数：
  0
• 氢受体数：
  20

反应信息

• 作为反应物：
  描述：

  8-methoxycarbonyloctyl O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside 在 sodium methylate 作用下， 以95%的产率得到8-methoxycarbonyloctyl β-D-galactopyranosyl-(1->4)-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of multivalent β-lactosyl clusters as potential tumor metastasis inhibitors

  摘要：

  A beta-lactosyl residue was linked to the amino groUpS Of L-lysyl-L-lysine through spacer arms of three different lengths (C2, C4, and C-9) to give trivalent beta-lactosyl clusters in order to increase the inhibitory activity of the beta-lactosyl group against tumor cell colonization. Thus, O-(2,3,4,6-tetra-0-acetyl-beta-D-galactopyranosyl)-(1 --> 4)-2,3,6-tri-O-acetyl-glucopyranosyl trichloroacetimidate was treated with methyl or benzyl hydroxyethanoate, methyl or benzyl 4-hydroxybutanoate, and methyl 9-hydroxynonanoate, respectively, in the presence of trimethylsilyl trifluoromethanesulfonate to give the corresponding beta-lactosides. These were coupled to L-lysyl-L-lysine, after conversion to the N-hydroxysuccinimide esters, to yield the corresponding trivalent beta-lactosyl-L-lysyl-L-lysine conjugates in good yields. The beta-lactosyl group with a C4 spacer arm was also coupled similarly to poly(L-lysine) (M(r) 3800) to form a polyvalent beta-lactosyl cluster. Coinjection of the trivalent (with C2 and C4 spacer arms) and polyvalent beta-lactosyl clusters with the highly metastatic B16 murine melanoma cells inhibited the formation of lung colonies in C57/BL mice, whereas the trivalent cluster with a C-9 spacer arm displayed no activity.

  DOI：

  10.1016/0008-6215(93)80071-l
• 作为产物：
  描述：

  4’-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-2’,3’,6’-tri-O-acetyl-D-glucopyranose 在 三氟甲磺酸三甲基硅酯 potassium carbonate 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 生成 8-methoxycarbonyloctyl O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of multivalent β-lactosyl clusters as potential tumor metastasis inhibitors

  摘要：

  A beta-lactosyl residue was linked to the amino groUpS Of L-lysyl-L-lysine through spacer arms of three different lengths (C2, C4, and C-9) to give trivalent beta-lactosyl clusters in order to increase the inhibitory activity of the beta-lactosyl group against tumor cell colonization. Thus, O-(2,3,4,6-tetra-0-acetyl-beta-D-galactopyranosyl)-(1 --> 4)-2,3,6-tri-O-acetyl-glucopyranosyl trichloroacetimidate was treated with methyl or benzyl hydroxyethanoate, methyl or benzyl 4-hydroxybutanoate, and methyl 9-hydroxynonanoate, respectively, in the presence of trimethylsilyl trifluoromethanesulfonate to give the corresponding beta-lactosides. These were coupled to L-lysyl-L-lysine, after conversion to the N-hydroxysuccinimide esters, to yield the corresponding trivalent beta-lactosyl-L-lysyl-L-lysine conjugates in good yields. The beta-lactosyl group with a C4 spacer arm was also coupled similarly to poly(L-lysine) (M(r) 3800) to form a polyvalent beta-lactosyl cluster. Coinjection of the trivalent (with C2 and C4 spacer arms) and polyvalent beta-lactosyl clusters with the highly metastatic B16 murine melanoma cells inhibited the formation of lung colonies in C57/BL mice, whereas the trivalent cluster with a C-9 spacer arm displayed no activity.

  DOI：

  10.1016/0008-6215(93)80071-l

文献信息

• Sabesan, Subramaniam; Lemieux, Raymond U., Canadian Journal of Chemistry, 1984, vol. 62, p. 644 - 654
  作者：Sabesan, Subramaniam、Lemieux, Raymond U.

  DOI：——

  日期：——
• Klotz, Wolfgang; Schmidt, Richard R., Journal of Carbohydrate Chemistry, 1994, vol. 13, # 8, p. 1093 - 1102
  作者：Klotz, Wolfgang、Schmidt, Richard R.

  DOI：——

  日期：——