2,4-di-O-acetyl-3,6-di-O-allyl-α-D-galactopyranosyl fluoride | 187157-55-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2,4-di-O-acetyl-3,6-di-O-allyl-α-D-galactopyranosyl fluoride
• CAS: 187157-55-7
• 化学式: C₁₆H₂₃FO₇
• 分子量: 346.353
• InChiKey: ZZWJMEUIFWJHMY-CWVYHPPDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.32
• 重原子数：
  24.0
• 可旋转键数：
  9.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  80.29
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  2,4-di-O-acetyl-3,6-di-O-allyl-α-D-galactopyranosyl fluoride 在 lithium hydroxide 、 PF4 、 4A molecular siebes 、 双氧水 、 silver trifluoromethanesulfonate 、 sodium hydride 、 tin(ll) chloride 作用下， 以 四氢呋喃 、 水 、 1,2-二氯乙烷 为溶剂， 反应 4.5h， 生成 tert-butyldiphenylsilyl 4,6-di-O-benzyl-β-D-galactopyranosyl-(1->3)-2-azido-2-deoxy-β-D-galactopyranoside
  参考文献：
  名称：

  Stereocontrolled syntheses of O-glycans of core class 2 with a linear tetrameric lactosamine chain and with three lactosamine branches

  摘要：

  Synthetic routes to O-glycans of core class 2 with a linearly extended tetralactosamine moiety and with three lactosamine branches are discussed. By a glycosyl fluoride-method, the mono- and the di-lactosaminyl units were attached to the core disaccharide (Gal beta 1-->3GalN(3)) derivatives in high stereoselectivity. (C) 1996 Elsevier Science Ltd.

  DOI：

  10.1016/s0008-6215(96)90116-0
• 作为产物：
  描述：

  Acetic acid (2R,3S,4S,5R)-5-acetoxy-4-allyloxy-2-allyloxymethyl-6-hydroxy-tetrahydro-pyran-3-yl ester 在 4,4'-二氨基二苯乙烯-2,2'-二磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 2,4-di-O-acetyl-3,6-di-O-allyl-β-D-galactopyranosyl fluoride 、 2,4-di-O-acetyl-3,6-di-O-allyl-α-D-galactopyranosyl fluoride
  参考文献：
  名称：

  Stereocontrolled syntheses of O-glycans of core class 2 with a linear tetrameric lactosamine chain and with three lactosamine branches

  摘要：

  Synthetic routes to O-glycans of core class 2 with a linearly extended tetralactosamine moiety and with three lactosamine branches are discussed. By a glycosyl fluoride-method, the mono- and the di-lactosaminyl units were attached to the core disaccharide (Gal beta 1-->3GalN(3)) derivatives in high stereoselectivity. (C) 1996 Elsevier Science Ltd.

  DOI：

  10.1016/s0008-6215(96)90116-0