(2R,3S,4S,5S,6R)-3,5-Bis-benzyloxy-2-fluoro-6-hydroxymethyl-tetrahydro-pyran-4-ol | 635316-98-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2R,3S,4S,5S,6R)-3,5-Bis-benzyloxy-2-fluoro-6-hydroxymethyl-tetrahydro-pyran-4-ol
• CAS: 635316-98-2
• 化学式: C₂₀H₂₃FO₅
• 分子量: 362.398
• InChiKey: VUMTWEIJPUDEFW-RMMWZPCPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  26.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  68.15
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  苯基 2,3,4,6-O-四乙酰基-alpha-D-硫代吡喃甘露糖苷 、 (2R,3S,4S,5S,6R)-3,5-Bis-benzyloxy-2-fluoro-6-hydroxymethyl-tetrahydro-pyran-4-ol 、 Acetic acid (2R,3R,4S,5S,6R)-3-acetoxy-2-acetoxymethyl-6-phenylsulfanyl-5-((2R,3S,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yl ester 在 N-碘代丁二酰亚胺 、 三氟甲磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以48%的产率得到Man2Ac3Ac4Ac6Ac(a1-2)Man3Ac4Ac6Ac(a1-6)[Man2Ac3Ac4Ac6Ac(a1-3)][Bn(-2)][Bn(-4)]a-Man1F
  参考文献：
  名称：

  Synthesis of an octamannosyled glycan chain, the key oligosaccharide structure in ER-associated degradation

  摘要：

  The high-mannose type decasaccharide (Man(8)GlcNAc(2)) the proposed ligand of ER residing mannosidase-like proteins (MLP), and its monoglycosylated homologue (alpha-Glc(1)Man(8)GlcNAc(2)) were synthesized. The oligosaccharide assembly was performed in a convergent and stereoselective manner, using three oligosaccharide components, a core trisaccharide having a beta-mannoside bond, a liner mannotriose, and a branched mannotetraose. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(03)00357-4
• 作为产物：
  描述：

  Acetic acid (2R,3R,4S,5S,6R)-2-acetoxymethyl-3,5-bis-benzyloxy-6-fluoro-tetrahydro-pyran-4-yl ester 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 4.0h， 生成 (2R,3S,4S,5S,6R)-3,5-Bis-benzyloxy-2-fluoro-6-hydroxymethyl-tetrahydro-pyran-4-ol
  参考文献：
  名称：

  Synthesis of an octamannosyled glycan chain, the key oligosaccharide structure in ER-associated degradation

  摘要：

  The high-mannose type decasaccharide (Man(8)GlcNAc(2)) the proposed ligand of ER residing mannosidase-like proteins (MLP), and its monoglycosylated homologue (alpha-Glc(1)Man(8)GlcNAc(2)) were synthesized. The oligosaccharide assembly was performed in a convergent and stereoselective manner, using three oligosaccharide components, a core trisaccharide having a beta-mannoside bond, a liner mannotriose, and a branched mannotetraose. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(03)00357-4