O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->3)-4,6-di-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl trichloroacetimidate | 875712-80-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->3)-4,6-di-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl trichloroacetimidate
• 英文别名: [(2R,3S,4R,5R,6S)-3-acetyloxy-5-(1,3-dioxoisoindol-2-yl)-4-[(2R,3R,4S,5S,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-6-(2,2,2-trichloroethanimidoyl)oxyoxan-2-yl]methyl acetate
• CAS: 875712-80-4
• 化学式: C₃₄H₃₇Cl₃N₂O₁₈
• 分子量: 868.029
• InChiKey: RQRZSZQUXCBGHI-ILEOCHLRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  57
• 可旋转键数：
  19
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  256
• 氢给体数：
  1
• 氢受体数：
  19

反应信息

• 作为反应物：
  描述：

  O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->3)-4,6-di-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl trichloroacetimidate 、 β-D-galactopyranosyl-(1->4)-1-thio-β-D-glucopyranoside 生成 lacto-N-tetraose
  参考文献：
  名称：

  Chemo-enzymatic supported synthesis of the 3-sulfated Lewisa pentasaccharide on a multimeric polyethylene glycol

  摘要：

  The 3-sulfated Lewis(a) pentasaccharide was synthesized on multimeric-based polyethylene glycol support. Coupling of O-(2,3,4,6-tetra-O-acetyl-beta-D-galactopyranosyl)-(1 -> 3)-4,6-di-O-acetyl-2-deoxy-2-phthalimido-beta-D-glucopyranosyl trichloroacetimidate with (2,6-di-O-acetyl-beta-D-galactopyranosyl)-(1 -> 4)-(2,3,6-tri-O-acetyl-beta-D-glucopyranoside) bound onto the polymer afforded lacto-N-tetraose, which was then regioselectively sulfated at the 3-OH position of the terminal galactose using the stannylene procedure. Fucosylation of the sulfated tetrasaccharide was performed using an immobilized fucosyltransferase FucTIII to give the title compound after cleavage. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2008.01.005
• 作为产物：
  描述：

  4-methoxybenzyl O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->3)-4,6-di-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranoside 在 ammonium cerium(IV) nitrate 、 sodium hydride 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 0.75h， 生成 O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->3)-4,6-di-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl trichloroacetimidate
  参考文献：
  名称：

  Chemoenzymatic synthesis of the 3-sulfated Lewisa pentasaccharide

  摘要：

  The sulfated pentasaccharide benzyl O-(3-O-sulfo-beta-D-galactopyranosyl)-(1 -> 3)-O-[(alpha-L-fucopyranosyl)-(1 -> 4)]-O-(2-acetamido -2-deoxy-beta-D-glucopyranosyl)-(1 -> 3)-O-(beta-D-galactopyranosyl)-(1 -> 4)-O-beta-D-glucopyranoside sodium salt was synthesized using a chemo-enzymatic approach. Lacto-N-tetraose, obtained from two disaccharides [4-metboxybenzyl O-(2,3,4,6-tetra- O-acetyl-beta-D-galactopranosyl)-(1 -> 3)-4,6-O-benzylidene-2-deoxy-2-phtalimido-beta-D-glucopyranoside and benzyl 2,6-di-O-acetyl -beta-D-galactopyranosyl-(1 -> 4)-2,3,6-tri -O-acetyl-beta-D-glucopyranoside], was regioselectively sulfated at the 3 OH position of the terminal galactose using the stannylene procedure. The fucosylation of the sulfated tetrasaccharide was performed using soluble or immobilized fucosyltransferase FucT-III to give the title compound. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2005.10.004