allyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->4)-3,6-di-O-acetyl-2-azido-2-deoxy-β-D-glucopyranoside | 104039-78-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: allyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->4)-3,6-di-O-acetyl-2-azido-2-deoxy-β-D-glucopyranoside
• 英文别名: Allyl-3,6-di-O-acetyl-2-azido-2-desoxy-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-glucopyranosid
• CAS: 104039-78-3
• 化学式: C₂₇H₃₇N₃O₁₆
• 分子量: 659.601
• InChiKey: RRMRGYJYHVIWMG-CERFIYQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.56
• 重原子数：
  46.0
• 可旋转键数：
  14.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  243.48
• 氢给体数：
  0.0
• 氢受体数：
  17.0

反应信息

• 作为反应物：
  描述：

  allyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->4)-3,6-di-O-acetyl-2-azido-2-deoxy-β-D-glucopyranoside 在 三苯基膦 作用下， 以 1,4-二氧六环 、 甲醇 、 水 为溶剂， 反应 20.0h， 生成
  参考文献：
  名称：

  Synthesis of 2-[(2-pyridyl)amino]ethyl β-d-lactosaminide and evaluation of its acceptor ability for sialyltransferase: a comparison with 4-methylumbelliferyl and dansyl β-d-lactosaminide

  摘要：

  We report the synthesis Of P-D-lactosaminide with a 2-aminopyridyl group that is linked to a glycosyl tether at the reducing end. This fluorescent disaccharide acts as an acceptor for both alpha-(2 --> 6)- and alpha-(2 --> 3)-sialyltransferases. In addition, the acceptor ability of this disaccharide was evaluated and compared with that Of beta-D-lactosaminide having a dansyl or a 4-methylumbelliferyl group. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2004.03.015
• 作为产物：
  描述：

  烯丙醇钠 、 3,6-di-O-acetyl-4-O-[2,3,4,6-tetra-O-acetyl-beta-D-galactopyranosyl]-2-azido-2-deoxy-alpha-D-glucopyranosyl chloride 以 二氯甲烷 为溶剂， 反应 0.17h， 以71%的产率得到allyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->4)-3,6-di-O-acetyl-2-azido-2-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of 2-[(2-pyridyl)amino]ethyl β-d-lactosaminide and evaluation of its acceptor ability for sialyltransferase: a comparison with 4-methylumbelliferyl and dansyl β-d-lactosaminide

  摘要：

  We report the synthesis Of P-D-lactosaminide with a 2-aminopyridyl group that is linked to a glycosyl tether at the reducing end. This fluorescent disaccharide acts as an acceptor for both alpha-(2 --> 6)- and alpha-(2 --> 3)-sialyltransferases. In addition, the acceptor ability of this disaccharide was evaluated and compared with that Of beta-D-lactosaminide having a dansyl or a 4-methylumbelliferyl group. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2004.03.015

文献信息

• Synthese eines N-acetylneuraminsäure-haltigen syntheseblocks. Kupplung zum N-acetylneuraminsäuretetrasaccharid mit trimethylsilyltriflat
  作者：Hans Paulsen、Holger Tietz

  DOI：10.1016/s0008-6215(00)90670-0

  日期：1985.12

  Abstract A trisaccharide synthetic block consisting of N -acetylneuraminic acid and lactosamine that allows general coupling reactions to other saccharide units was obtained. O -(Methyl 5-acetamido-4,7,8,9-tetra- O -acetyl-3,5-dideoxy-α- and -β- d - glycero - d - galacto -2-nonulopyranosylonate)-(2→6)- O -(2,3,4-tri- O -acetyl-β- d -galactopyranosyl)-(1→4)-1,3,6-tri- O -acetyl-2-desoxy-2-phthalimido-β-

  摘要获得了由N-乙酰神经氨酸和乳糖胺组成的三糖合成嵌段，该嵌段可与其他糖单元进行一般偶联反应。O-（5-乙酰氨基-4,7,8,9-四-甲基-O-乙酰基-3,5-二脱氧-α-和-β-d-甘油-d-半乳清-2-壬基吡喃二磺酸酯）-（2→ 6）-O-（2,3,4-三-O-乙酰基-β-d-吡喃半乳糖基）-（1→4）-1,3,6-三-O-乙酰基-2-脱氧-2-邻苯二甲酰亚胺基-β-d-吡喃葡萄糖被用作糖基供体。在三甲基甲硅烷基三氟甲基磺酸盐的存在下，通过与在OH-2处代表糖基受体的未取代的d-甘露糖衍生物反应，将两种化合物转化为四糖。除去保护基团得到O-（5-乙酰氨基-3，