succinimidoxycarbonylmethyl O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside | 152733-57-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: succinimidoxycarbonylmethyl O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside
• CAS: 152733-57-8
• 化学式: C₃₂H₄₁NO₂₂
• 分子量: 791.671
• InChiKey: OUTLJNOLEATUFJ-QEQQHPKHSA-N

物化性质

• 沸点：
  772.8±70.0 °C(predicted)
• 密度：
  1.45±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.77
• 重原子数：
  55.0
• 可旋转键数：
  15.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  284.7
• 氢给体数：
  0.0
• 氢受体数：
  22.0

反应信息

• 作为反应物：
  描述：

  L-lysyl-L-lysine dihydrochloride 、 succinimidoxycarbonylmethyl O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside 在 三乙胺 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以69%的产率得到
  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：

  2,3,6,2',3',4',6'-hepta-O-acetyl-α-D-lactosyl trichloroacetimidate 在 palladium on activated charcoal 、 三氟甲磺酸三甲基硅酯 氢气 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 10.5h， 生成 succinimidoxycarbonylmethyl 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