4-Methyl-benzoic acid (2R,3S,4S,5R,6S)-3,5-bis-benzyloxy-6-[(2R,3S,4R,5R,6S)-4-benzyloxy-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-fluoro-tetrahydro-pyran-3-yloxy]-4-(2-chloro-acetoxy)-tetrahydro-pyran-2-ylmethyl ester | 187157-20-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-Methyl-benzoic acid (2R,3S,4S,5R,6S)-3,5-bis-benzyloxy-6-[(2R,3S,4R,5R,6S)-4-benzyloxy-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-fluoro-tetrahydro-pyran-3-yloxy]-4-(2-chloro-acetoxy)-tetrahydro-pyran-2-ylmethyl ester
• CAS: 187157-20-6
• 化学式: C₅₈H₅₅ClFNO₁₃
• 分子量: 1028.53
• InChiKey: YYWVKPFEIQRGEB-XAOCWQCNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.74
• 重原子数：
  74.0
• 可旋转键数：
  21.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  154.59
• 氢给体数：
  0.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  4-Methyl-benzoic acid (2R,3R,4S,5R,6S)-3,5-bis-benzyloxy-6-[(2R,3S,4R,5R,6S)-4-benzyloxy-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-(4-methoxy-phenoxy)-tetrahydro-pyran-3-yloxy]-4-hydroxy-tetrahydro-pyran-2-ylmethyl ester 、 4-Methyl-benzoic acid (2R,3S,4S,5R,6S)-3,5-bis-benzyloxy-6-[(2R,3S,4R,5R,6S)-4-benzyloxy-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-fluoro-tetrahydro-pyran-3-yloxy]-4-(2-chloro-acetoxy)-tetrahydro-pyran-2-ylmethyl ester 在 二氯二茂铪 、 4 A molecular sieve 、 silver trifluoromethanesulfonate 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以81%的产率得到4-methoxyphenyl 2,4-di-O-benzyl-3-O-chloroacetyl-6-O-(4-methylbenzoyl)-β-D-galactopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1->3)-2,4-di-O-benzyl-6-O-(4-methylbenzoyl)-β-D-galactopyranosyl-...
  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：

  4-Methyl-benzoic acid (2R,3S,4S,5R,6S)-3,5-bis-benzyloxy-6-[(2R,3S,4R,5R,6S)-4-benzyloxy-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-(4-methoxy-phenoxy)-tetrahydro-pyran-3-yloxy]-4-(2-chloro-acetoxy)-tetrahydro-pyran-2-ylmethyl ester 在 ammonium cerium(IV) nitrate 、 4,4'-二氨基二苯乙烯-2,2'-二磺酸 作用下， 以 二氯甲烷 、 水 、 甲苯 、 乙腈 为溶剂， 反应 2.83h， 生成 4-Methyl-benzoic acid (2R,3S,4S,5R,6S)-3,5-bis-benzyloxy-6-[(2R,3S,4R,5R,6S)-4-benzyloxy-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-fluoro-tetrahydro-pyran-3-yloxy]-4-(2-chloro-acetoxy)-tetrahydro-pyran-2-ylmethyl ester
  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