2,6-dimethylphenylthio 3-O-(2-O-benzoyl-6-O-benzyl-3-O-(methyl 7-O-acetyl-5-amino-9-O-benzyl-5-N,4-O-carbonyl-3,5-dideoxy-8-O-(methyl 7,8-di-O-acetyl-5-amino-9-O-benzyl-5-N,4-O-carbonyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonate)-D-glycero-α-D-galacto-2-nonulopyranoylonate)-4-O-(2,2,2-trichloroethoxycarbonyl)-β-D-galactopyranoside)-4,6-di-O-benzyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-galactopyranoside | 1093982-51-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,6-dimethylphenylthio 3-O-(2-O-benzoyl-6-O-benzyl-3-O-(methyl 7-O-acetyl-5-amino-9-O-benzyl-5-N,4-O-carbonyl-3,5-dideoxy-8-O-(methyl 7,8-di-O-acetyl-5-amino-9-O-benzyl-5-N,4-O-carbonyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonate)-D-glycero-α-D-galacto-2-nonulopyranoylonate)-4-O-(2,2,2-trichloroethoxycarbonyl)-β-D-galactopyranoside)-4,6-di-O-benzyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-galactopyranoside
• 英文别名: N-[(2S,3R,4R,5R,6R)-4-[(2R,3R,4S,5S,6R)-4-[[(3aR,4R,6S,7aS)-4-[(1S,2R)-2-[[(3aR,4R,6S,7aS)-4-[(1S,2R)-1,2-diacetyloxy-3-phenylmethoxypropyl]-2-hydroxy-6-methoxycarbonyl-3a,4,7,7a-tetrahydropyrano[3,4-d][1,3]oxazol-6-yl]oxy]-1-acetyloxy-3-phenylmethoxypropyl]-2-hydroxy-6-methoxycarbonyl-3a,4,7,7a-tetrahydropyrano[3,4-d][1,3]oxazol-6-yl]oxy]-3-benzoyloxy-6-(phenylmethoxymethyl)-5-(2,2,2-trichloroethoxycarbonyloxy)oxan-2-yl]oxy-2-(2,6-dimethylphenyl)sulfanyl-5-phenylmethoxy-6-(phenylmethoxymethyl)oxan-3-yl]-1-(2,2,2-trichloroethoxy)methanimidic acid
• CAS: 1093982-51-4
• 化学式: C₉₆H₁₀₃Cl₆N₃O₃₃S
• 分子量: 2071.66
• InChiKey: VETUXTMNSBBOHG-KWYYJMDHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14.4
• 重原子数：
  139
• 可旋转键数：
  51
• 环数：
  13.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  455
• 氢给体数：
  3
• 氢受体数：
  37

反应信息

• 作为产物：
  描述：

  2,6-dimethylphenylthio 4,6-di-O-benzyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-galactopyranoside 、 2-O-benzoyl-6-O-benzyl-3-O-(methyl 7-O-acetyl-5-amino-9-O-benzyl-5-N,4-O-carbonyl-3,5-dideoxy-8-O-(methyl 7,8-di-O-acetyl-5-amino-9-O-benzyl-5-N,4-O-carbonyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonate)-D-glycero-α-D-galacto-2-nonulopyranoylonate)-4-O-(2,2,2-trichloroethoxycarbonyl)-D-galactopyranosyl trichloroacetimidate 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以95%的产率得到2,6-dimethylphenylthio 3-O-(2-O-benzoyl-6-O-benzyl-3-O-(methyl 7-O-acetyl-5-amino-9-O-benzyl-5-N,4-O-carbonyl-3,5-dideoxy-8-O-(methyl 7,8-di-O-acetyl-5-amino-9-O-benzyl-5-N,4-O-carbonyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonate)-D-glycero-α-D-galacto-2-nonulopyranoylonate)-4-O-(2,2,2-trichloroethoxycarbonyl)-β-D-galactopyranoside)-4,6-di-O-benzyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-galactopyranoside
  参考文献：
  名称：

  An Efficient Convergent Synthesis of GP1c Ganglioside Epitope

  摘要：

  In this report, we describe an efficient convergent synthesis of the GP1c glycolipid epitope, which is one of the most complex c-series gangliosides. The alpha(2,3) and alpha(2,8) sialylations were accomplished by use of 5N,4O-carbonyl and 7,8-O-isopropyliden as well as 5N,4O-carbonyl- and 7,8-di-O-chloroacetyl-protected sialyl donors in good yields with excellent alpha-selectivity, respectively. The two sialyl donors enable synthesis of the di- and trisialylgalactosides by simple glycosylation and deprotection. We synthesized the protected GP1c glycolipid epitope, which is a compact, rigid, branched structure, via direct coupling of tetarasaccharide and pentasaccharide units.

  DOI：

  10.1021/ja807482t