Chloro-acetic acid (2S,3R,4S,5S,6R)-3-acetoxy-6-acetoxymethyl-2-[(2R,3S,4R,5R,6S)-4-benzyloxy-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-ethylsulfanyl-tetrahydro-pyran-3-yloxy]-5-(2-chloro-acetoxy)-tetrahydro-pyran-4-yl ester | 390400-37-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Chloro-acetic acid (2S,3R,4S,5S,6R)-3-acetoxy-6-acetoxymethyl-2-[(2R,3S,4R,5R,6S)-4-benzyloxy-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-ethylsulfanyl-tetrahydro-pyran-3-yloxy]-5-(2-chloro-acetoxy)-tetrahydro-pyran-4-yl ester
• CAS: 390400-37-0
• 化学式: C₄₄H₄₇Cl₂NO₁₅S
• 分子量: 932.827
• InChiKey: JRGVLYXKWHBQGF-HIDMNPIESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.84
• 重原子数：
  63.0
• 可旋转键数：
  19.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  188.73
• 氢给体数：
  0.0
• 氢受体数：
  16.0

反应信息

• 作为反应物：
  描述：

  Chloro-acetic acid (2S,3R,4S,5S,6R)-3-acetoxy-6-acetoxymethyl-2-[(2R,3S,4R,5R,6S)-4-benzyloxy-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-ethylsulfanyl-tetrahydro-pyran-3-yloxy]-5-(2-chloro-acetoxy)-tetrahydro-pyran-4-yl ester 、 在 DMTST 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以54%的产率得到
  参考文献：
  名称：

  Efficient synthesis of lactosaminylated core-2 O-glycans

  摘要：

  A series of lactosaminylated oligosaccharides found in mucin type O-glycans was synthesized using a generalized block strategy. The synthesis involved the addition of a protected lactosamine donor to a partially protected T-disaccharide derivative. The nonreducing galactose residues of the deblocked oligosaccharide products could be removed by beta -galactosidase from jack bean to produce the corresponding GlcNAc terminated compounds. A series of tri- to hexasaccharides was thus efficiently produced. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00550-9
• 作为产物：
  描述：

  乙基3,4,6-三-O-乙酰基-2-脱氧-2-邻苯二甲酰亚胺基-1-硫代-β-D-吡喃葡萄糖苷 在 2,4,6-三甲基吡啶 、 盐酸 、 sodium methylate 、 silver trifluoromethanesulfonate 、 sodium hydride 、 sodium cyanoborohydride 、 对甲苯磺酸 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 8.33h， 生成 Chloro-acetic acid (2S,3R,4S,5S,6R)-3-acetoxy-6-acetoxymethyl-2-[(2R,3S,4R,5R,6S)-4-benzyloxy-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-ethylsulfanyl-tetrahydro-pyran-3-yloxy]-5-(2-chloro-acetoxy)-tetrahydro-pyran-4-yl ester
  参考文献：
  名称：

  Efficient synthesis of lactosaminylated core-2 O-glycans

  摘要：

  A series of lactosaminylated oligosaccharides found in mucin type O-glycans was synthesized using a generalized block strategy. The synthesis involved the addition of a protected lactosamine donor to a partially protected T-disaccharide derivative. The nonreducing galactose residues of the deblocked oligosaccharide products could be removed by beta -galactosidase from jack bean to produce the corresponding GlcNAc terminated compounds. A series of tri- to hexasaccharides was thus efficiently produced. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00550-9