p-methoxybenzyl 2-deoxy-2-phthalimido-β-D-glucopyranoside | 93417-35-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: p-methoxybenzyl 2-deoxy-2-phthalimido-β-D-glucopyranoside
• CAS: 93417-35-7
• 化学式: C₂₂H₂₃NO₈
• 分子量: 429.427
• InChiKey: KVBIBDMPVUWORY-ACMVSEJYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.32
• 重原子数：
  31.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  125.76
• 氢给体数：
  3.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  p-methoxybenzyl 2-deoxy-2-phthalimido-β-D-glucopyranoside 在 camphor-10-sulfonic acid 、 四丁基碘化铵 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 4-methoxybenzyl 2-deoxy-3-O-(4-methoxybenzyl)-4,6-O-(4-methoxybenzylidene)-2-phthalimido-β-D-glucopyranoside
  参考文献：
  名称：

  Enzymatic glycosidation of sugar oxazolines having a carboxylate group catalyzed by chitinase

  摘要：

  Enzymatic glycosidation using sugar oxazolines 1-3 having a carboxylate group as glycosyl donors and compounds 4-6 as glycosyl acceptors was performed by employing a chitinase from Bacillus sp. as catalyst. All the glycosidations proceeded with full control in stereochemistry at the anomeric carbon of the donor and regio-selectivity of the acceptor. The N,N'-diacetyl-6'-O-carboxymethyl chitobiose oxazoline derivative 1 was effectively glycosidated, under catalysis by the enzyme, with methyl N,N'-diacetyl-beta-chitobioside (4), pent-4-enyl N-acetyl-beta-D-glucosaminide (5), and methyl N-acetyl-beta-D-glucosaminide (6), affording in good yields the corresponding oligosaccharide derivatives having 6-O-carboxymethyl group at the nonreducing GlcNAc residue. The N,N'-diacetyl-6-O-carboxymethylchitobiose oxazoline derivative 2 was subjected to catalysis by the enzyme catalysis; however, no glycosidated products were produced through the reactions with 4, 5, and 6. Glycosidation reactions of the beta-D-glycosyluronic(1-->4)-N-acetyl-D-glucosamine oxazoline derivative 3 proceeded with each of the glycosyl acceptors, giving rise to the corresponding oligosaccharide derivative having a GlcA residue at their nonreducing termini in good yields. (C) 2004 Published by Elsevier Ltd.

  DOI：

  10.1016/j.carres.2004.08.016
• 作为产物：
  描述：

  4-甲氧基苄醇 在 2,4,6-三甲基吡啶 、 sodium methylate 、 silver trifluoromethanesulfonate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 p-methoxybenzyl 2-deoxy-2-phthalimido-β-D-glucopyranoside
  参考文献：
  名称：

  Classon, Bjoern; Garegg, Per J.; Samuelsson, Bertil, Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1984, vol. 38, # 5, p. 419 - 422

  摘要：

  DOI：

文献信息

• Synthesis of 3E- And 6E-Monosulfated and 3E,6E-Disulfated Lewis X Pentasaccharides, Candidate Ligands for Human L-Selectin
  作者：André Lubineau、Jocelyne Alais、Remy Lemoine

  DOI：10.1080/07328300008544072

  日期：2000.1

  Condensation of perbenzyl fucosyl bromide 4 with the known 2-acetamido derivative 1 and with the 2-phthalimido analog 3 gave, respectively, disaccharides 5 and 6 which, after reductive opening of the benzylidene group were glycosylated using peracetylated galactose trichloroacetimidate to give trisaccharides 10 and 11. After removal of the anomeric p-methoxybenzyl group and subsequent activation as the trichloroacetimidate, condensation onto the known lactose derivative 16 afforded protected pentasaccharides 18 and 17 in 24 and 70% yields, respectively. Compound 17 was transformed into 18 by a conventional method in 77% yield making the phthalimido route overall more attractive. The terminal galactose was then selectively deprotected and sulfated at the 3e, 6e and both 3e,6e positions to give the title compounds after complete deprotection.