pent-4-enyl 4-O-(2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-β-D-galactopyranosyl)-2-O-acetyl-3-O-benzyl-6-O-(chloroacetyl)-α-D-mannopyranoside | 150772-65-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: pent-4-enyl 4-O-(2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-β-D-galactopyranosyl)-2-O-acetyl-3-O-benzyl-6-O-(chloroacetyl)-α-D-mannopyranoside
• 英文别名: [(2R,3R,4S,5S,6S)-3-[(2S,3R,4R,5R,6R)-3-acetamido-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxy-5-acetyloxy-6-pent-4-enoxy-4-phenylmethoxyoxan-2-yl]methyl 2-chloroacetate
• CAS: 150772-65-9
• 化学式: C₅₁H₆₀ClNO₁₃
• 分子量: 930.489
• InChiKey: ZHVDDDVGJGPLGA-UZNDZEKYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  66
• 可旋转键数：
  27
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  156
• 氢给体数：
  1
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  pent-4-enyl 4-O-(2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-β-D-galactopyranosyl)-2-O-acetyl-3-O-benzyl-6-O-(chloroacetyl)-α-D-mannopyranoside 、 1-O-Allyl-2,3,4,5-tetra-O-benzyl-6-O-(2-azido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-D-myo-inositol 在 N-碘代丁二酰亚胺 、 三乙基硅基三氟甲磺酸酯 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 以55%的产率得到O-(2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-β-D-galactopyranosyl)-(1-4)-O-(2-O-acetyl-3-O-benzyl-6-O-(chloroacetyl)-α-D-mannopyranosyl)-(1-4)-O-(2-azido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1-6)-1-O-allyl-2,3,4,5-tetra-O-benzyl-D-myo-inosito
  参考文献：
  名称：

  A ready, convergent synthesis of the heptasaccharide GPI membrane anchor of rat brain Thy-1 glycoprotein

  摘要：

  DOI：

  10.1021/ja00070a048
• 作为产物：
  描述：

  pent-4-enyl 2,6-di-O-acetyl-3-O-benzyl-α-D-mannopyranoside 在 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 、 三乙胺 、 甲胺 作用下， 以 甲苯 为溶剂， 反应 2.0h， 生成 pent-4-enyl 4-O-(2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-β-D-galactopyranosyl)-2-O-acetyl-3-O-benzyl-6-O-(chloroacetyl)-α-D-mannopyranoside
  参考文献：
  名称：

  A ready, convergent synthesis of the heptasaccharide GPI membrane anchor of rat brain Thy-1 glycoprotein

  摘要：

  DOI：

  10.1021/ja00070a048
• 作为试剂：
  描述：

  Trifluor-essigsaeure-triethyl-silylester 、 1-O-Allyl-2,3,4,5-tetra-O-benzyl-6-O-(2-azido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-D-myo-inositol 在 N-碘代丁二酰亚胺 、 pent-4-enyl 4-O-(2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-β-D-galactopyranosyl)-2-O-acetyl-3-O-benzyl-6-O-(chloroacetyl)-α-D-mannopyranoside 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 以66%的产率得到O-(2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-β-D-galactopyranosyl)-(1-4)-O-(2-O-acetyl-3-O-benzyl-6-O-(chloroacetyl)-α-D-mannopyranosyl)-(1-4)-O-(2-azido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1-6)-1-O-allyl-2,3,4,5-tetra-O-benzyl-D-myo-inosito
  参考文献：
  名称：

  Studies Related to Synthesis of Glycophosphatidylinositol Membrane-Bound Protein Anchors. 6. Convergent Assembly of Subunits

  摘要：

  Glycophosphatidylinositol anchors of membrane-bound proteins are thought to comprise a common pentasaccharide core containing mannan, glucosamine, and inositol residues. A synthetic route to this core is described. In addition, the complete heptasaccharide moiety of the rat brain Thy-1 membrane anchor, the first mammalian membrane anchor to be characterized, has been synthesized. In the case of the Thy-1 anchor, the synthetic plan is based on three building blocks comprising glucosamine-inositol, galactosamine-mannose, and trimannan residues. Although glycosyl donors other than n-pentenyl glycosides (NPGs) have been used in preparing each of these building blocks, the final assembly of the heptasaccharide utilizes NPGs as the only glycosyl donors. The mildness of the conditions for these coupling reactions has allowed us to make provisions for subsequent installation of the three phosphodiester units.

  DOI：

  10.1021/ja00110a011