2,3,4-tri-O-benzyl-β-L-fucopyranosyl 2-thiopyridyl carbonate | 160776-15-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3,4-tri-O-benzyl-β-L-fucopyranosyl 2-thiopyridyl carbonate
• 英文别名: [(2R,3S,4R,5R,6S)-6-methyl-3,4,5-tris(phenylmethoxy)oxan-2-yl] pyridin-2-ylsulfanylformate
• CAS: 160776-15-8
• 化学式: C₃₃H₃₃NO₆S
• 分子量: 571.694
• InChiKey: WJTSIQWKIWLJNR-RCANJRTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  41
• 可旋转键数：
  13
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  101
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2,3,4-tri-O-benzyl-β-L-fucopyranosyl 2-thiopyridyl carbonate 在 四丁基溴化铵 、 sodium methylate 、 二正丁基氧化锡 、 copper(ll) bromide 作用下， 以 二氯甲烷 为溶剂， 反应 33.0h， 生成
  参考文献：
  名称：

  Exploration of β-turn scaffolding motifs as components of sialyl LeX mimetics and their relevance to P-selectin

  摘要：

  Monocyclic and bicyclic lactam units representing P-turn surrogates were incorporated into a sialyl Le(X) structure by replacement of the natural sugar components. I;ow micromolar activity was found in a new P-selectin binding assay.(C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00500-9
• 作为产物：
  描述：

  Di-S-(2-pyridyl) dithiocarbonate 、 (3S,4R,5R,6S)-3,4,5-tris(benzyloxy)-6-methyltetrahydro-2H-pyran-2-ol 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 生成 2,3,4-tri-O-benzyl-β-L-fucopyranosyl 2-thiopyridyl carbonate
  参考文献：
  名称：

  通过新的异头活化立体控制合成1,2-反式己基吡喃糖基核苷

  摘要：

  2-（2'，3'，4'，6'-四-O-苄基-β-D-己吡喃糖基氧基）-3-甲氧基吡啶的偶合以及2-（2'，3'，4'，6通过与三氟甲磺酸三甲基甲硅烷基酯和三氟甲磺酸银活化而具有甲硅烷基化的嘧啶碱基的'-四-O-苄基-β-D-己吡喃糖基）-硫代吡啶基碳酸酯分别以高选择性提供了相应的1,2-反式核苷。

  DOI：

  10.1016/0040-4020(96)00611-4

文献信息

• The stereocontrolled synthesis of 1,2-trans hexopyranosyl nucleosides via a novel anomeric activation
  作者：Stephen Hanessian、Jose J. Conde、Hoan Huynh Khai、Boliang Lou

  DOI：10.1016/0040-4020(96)00611-4

  日期：1996.8

  yranosyl)-thiopyridylcarbonate, with silylated pyrimidine bases by activation with trimethylsilyl trifluoromethanesulfonate and silver triflate respectively afforded the corresponding 1,2-trans nucleosides with high selectivity.

  2-（2'，3'，4'，6'-四-O-苄基-β-D-己吡喃糖基氧基）-3-甲氧基吡啶的偶合以及2-（2'，3'，4'，6通过与三氟甲磺酸三甲基甲硅烷基酯和三氟甲磺酸银活化而具有甲硅烷基化的嘧啶碱基的'-四-O-苄基-β-D-己吡喃糖基）-硫代吡啶基碳酸酯分别以高选择性提供了相应的1,2-反式核苷。
• Design and synthesis of sialyl Lex mimetics based on carbocyclic scaffolds derived from (−) quinic acid
  作者：Stephen Hanessian、Gurijala V. Reddy、Hoan K. Huynh、Jingwen Pan、Silvana Pedatella、Beat Ernst、Hartmuth C. Kolb

  DOI：10.1016/s0960-894x(97)10077-4

  日期：1997.11

  The synthesis of sialyl Lewis(x) mimetic anologs in which the D-glucosamine, D-galactose, and sialic acid residues are replaced individually with appropriate glycomimetics is described. A computational model for predicting bioactive conformations was tested. (C) 1997 Elsevier Science Ltd.
• Synthesis of a Potent Antagonist of E-Selectin
  作者：Stephen Hanessian、Vincent Mascitti、Olivier Rogel

  DOI：10.1021/jo0110956

  日期：2002.5.1

  A synthesis of an antagonist of E-selectin previously reported by a group at Novartis Pharma in Basel is described. An important feature involves the formation of an ether linkage based on a Rh-II-catalyzed reaction. Stereocontrolled glycosylations rely on the anomeric activation of 2-pyridylthio carbonate as leaving group for the attachment of beta-D-galactopyranosyl and alpha-L-fucopyranosyl units on a common 1,5-anhydro D-glucitol scaffold.
• Exploration of β-turn scaffolding motifs as components of sialyl LeX mimetics and their relevance to P-selectin
  作者：Stephen Hanessian、Hoan K. Huynh、Gurijala V. Reddy、Grant McNaughton-Smith、Beat Ernst、Hartmuth C. Kolb、John Magnani、Charla Sweeley

  DOI：10.1016/s0960-894x(98)00500-9

  日期：1998.10

  Monocyclic and bicyclic lactam units representing P-turn surrogates were incorporated into a sialyl Le(X) structure by replacement of the natural sugar components. I;ow micromolar activity was found in a new P-selectin binding assay.(C) 1998 Elsevier Science Ltd. All rights reserved.