3-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-2,4,6-tri-O-acetyl-α-D-galactopyranosyl trichloroacetimidate | 383905-66-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-2,4,6-tri-O-acetyl-α-D-galactopyranosyl trichloroacetimidate
• 英文别名: Bn(-2)[Bn(-3)][Bn(-4)][Bn(-6)]Gal(a1-3)Gal2Ac4Ac6Ac(a)-O-C(NH)CCl3；[(2R,3S,4S,5R,6R)-3,5-diacetyloxy-6-(2,2,2-trichloroethanimidoyl)oxy-4-[(2R,3R,4S,5S,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxyoxan-2-yl]methyl acetate
• CAS: 383905-66-6
• 化学式: C₄₈H₅₂Cl₃NO₁₄
• 分子量: 973.298
• InChiKey: RRYYFJGOSOHFAI-HCDZPIIISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  66
• 可旋转键数：
  24
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  177
• 氢给体数：
  1
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  3-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-2,4,6-tri-O-acetyl-α-D-galactopyranosyl trichloroacetimidate 、 三乙二醇 在 molecular sieve 、 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 0.33h， 以57%的产率得到3,6-dioxaoct-1,8-diyl-di-[2,4,6-tri-O-acetyl-3-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-β-D-galactopyranoside]
  参考文献：
  名称：

  Synthesis of a divalent glycoside of an α-galactosyl disaccharide epitope involved in the hyperacute rejection of xenotransplantation

  摘要：

  3,6-Dioxaoct-1,8-diyl di-(3-O-alpha -D-galactopyranosyl-beta -D-galactopyranoside) was synthesized for use in research on hyperacute rejection of xeno transplantation. The trichloroacetate method was successfully applied to form stereoselectively the a-D-galactosyl linkage under mild reaction conditions and a simple procedure. The divalent O-glycoside was formed from the corresponding trichloroacetimidate in one step with reasonable yield. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(01)00194-x
• 作为产物：
  描述：

  p-methoxyphenyl 3-O-benzyl-β-D-galactopyranoside 在 palladium on activated charcoal 吡啶 、 molecular sieve 、 ammonium cerium(IV) nitrate 、 三氟甲磺酸三甲基硅酯 、 氢气 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 37.5h， 生成 3-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-2,4,6-tri-O-acetyl-α-D-galactopyranosyl trichloroacetimidate
  参考文献：
  名称：

  Synthesis of a divalent glycoside of an α-galactosyl disaccharide epitope involved in the hyperacute rejection of xenotransplantation

  摘要：

  3,6-Dioxaoct-1,8-diyl di-(3-O-alpha -D-galactopyranosyl-beta -D-galactopyranoside) was synthesized for use in research on hyperacute rejection of xeno transplantation. The trichloroacetate method was successfully applied to form stereoselectively the a-D-galactosyl linkage under mild reaction conditions and a simple procedure. The divalent O-glycoside was formed from the corresponding trichloroacetimidate in one step with reasonable yield. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(01)00194-x