phenyl 2,3,6-tri-O-benzyl-4-O-(3,4,6-tri-O-benzyl-2-deoxy-β-D-lyxo-hexopyranosyl)-β-D-glucopyranoside | 847237-61-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl 2,3,6-tri-O-benzyl-4-O-(3,4,6-tri-O-benzyl-2-deoxy-β-D-lyxo-hexopyranosyl)-β-D-glucopyranoside
• CAS: 847237-61-0
• 化学式: C₆₀H₆₂O₁₀
• 分子量: 943.146
• InChiKey: RHOPZCLTDVHOAX-WHDZMBBJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.07
• 重原子数：
  70.0
• 可旋转键数：
  24.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  92.3
• 氢给体数：
  0.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  phenyl 2,3,6-tri-O-benzyl-4-O-(3,4,6-tri-O-benzyl-2-deoxy-β-D-lyxo-hexopyranosyl)-β-D-glucopyranoside 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 以74%的产率得到phenyl 4-O-(2-deoxy-β-D-lyxo-hexopyranosyl)-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of deoxy and acylamino derivatives of lactose and use of these for probing the active site of Neisseria meningitidis N-acetylglucosaminyltransferase

  摘要：

  Derivatives of lactose with the galactose ring substituents replaced by deoxy or acylamino functions were prepared. The 2'-, 3'-. 4'- and 6'-deoxy, 3'-acetamido and 3'-benzamido derivatives of phenyl 4-O-(beta-D-galactopyranosyl)-beta-D-glucopyranoside (phenyl P-lactoside) were synthesized from disaccharide or monosaccharide precursors. The derivatives were tested as substrates for the N-acetylglucosaminyltransferase from Neisseria meningitidis, which uses lactosyl derivatives as acceptors and UDP-GlcNAc as the donor in a beta-(1-->3) glycosylation reaction. The 6'-deoxy derivative was nearly threefold as active as phenyl beta-lactoside, whereas the 2'- and 4'-deoxy derivatives were less active. The other derivatives were inactive, as expected. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2004.11.017
• 作为产物：
  描述：

  (4aR,6S,7R,8S,8aR)-6-phenoxy-2-phenyl-7,8-bis(phenylmethoxy)-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxine 在 咪唑 、 盐酸 、 偶氮二异丁腈 、 4 A molecular sieve 、 三正丁基氢锡 、 sodium methylate 、 sodium hydride 、 sodium cyanoborohydride 、 DMTST 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 、 甲苯 为溶剂， 反应 10.0h， 生成 phenyl 2,3,6-tri-O-benzyl-4-O-(3,4,6-tri-O-benzyl-2-deoxy-β-D-lyxo-hexopyranosyl)-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of deoxy and acylamino derivatives of lactose and use of these for probing the active site of Neisseria meningitidis N-acetylglucosaminyltransferase

  摘要：

  Derivatives of lactose with the galactose ring substituents replaced by deoxy or acylamino functions were prepared. The 2'-, 3'-. 4'- and 6'-deoxy, 3'-acetamido and 3'-benzamido derivatives of phenyl 4-O-(beta-D-galactopyranosyl)-beta-D-glucopyranoside (phenyl P-lactoside) were synthesized from disaccharide or monosaccharide precursors. The derivatives were tested as substrates for the N-acetylglucosaminyltransferase from Neisseria meningitidis, which uses lactosyl derivatives as acceptors and UDP-GlcNAc as the donor in a beta-(1-->3) glycosylation reaction. The 6'-deoxy derivative was nearly threefold as active as phenyl beta-lactoside, whereas the 2'- and 4'-deoxy derivatives were less active. The other derivatives were inactive, as expected. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2004.11.017