4-O-(2-O-acetyl-3,4-di-O-benzoyl-α-L-rhamnopyranosyl)-2,3,6-tri-O-benzoyl-α-D-mannopyranosyl trichloroacetimidate | 228717-40-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-O-(2-O-acetyl-3,4-di-O-benzoyl-α-L-rhamnopyranosyl)-2,3,6-tri-O-benzoyl-α-D-mannopyranosyl trichloroacetimidate
• 英文别名: Bz(-3)[Bz(-4)]Rha2Ac(a1-4)[Bz(-2)][Bz(-3)][Bz(-6)]Man(a)-O-C(NH)CCl3；[(2R,3R,4S,5S,6R)-3-[(2S,3R,4R,5S,6S)-3-acetyloxy-4,5-dibenzoyloxy-6-methyloxan-2-yl]oxy-4,5-dibenzoyloxy-6-(2,2,2-trichloroethanimidoyl)oxyoxan-2-yl]methyl benzoate
• CAS: 228717-40-6
• 化学式: C₅₁H₄₄Cl₃NO₁₆
• 分子量: 1033.27
• InChiKey: KFFRVIALGLDNGM-ZJKXVLOSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10
• 重原子数：
  71
• 可旋转键数：
  22
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  219
• 氢给体数：
  1
• 氢受体数：
  17

反应信息

• 作为反应物：
  描述：

  allyl 4-O-(2-O-acetyl-4-O-benzoyl-α-L-rhamnopyranosyl)-2,3,6-tri-O-benzoyl-α-D-mannopyranoside 、 4-O-(2-O-acetyl-3,4-di-O-benzoyl-α-L-rhamnopyranosyl)-2,3,6-tri-O-benzoyl-α-D-mannopyranosyl trichloroacetimidate 在 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 作用下， 以 二氯甲烷 为溶剂， 反应 0.67h， 以75%的产率得到allyl 4-O-{3-O-[4-O-(2-O-acetyl-3,4-di-O-benzoyl-α-L-rhamnopyranosyl)-2,3,6-tri-O-benzoyl-α-D-mannopyranosyl]-2-O-acetyl-4-O-benzoyl-α-L-rhamnopyranosyl}-2,3,6-tri-O-benzoyl-α-D-mannopyranoside
  参考文献：
  名称：

  A highly efficient and convergent synthesis of a hexasaccharide, a dimer of the repeating unit of the antigen O2 polysaccharide of Stenotrophomonas maltophilia

  摘要：

  A highly efficient and convergent synthesis of a hexasaccharide, which is a dimer of the repeating unit of the antigen O2 polysaccharide of Stenotrophomonas maltophilia, was achieved via coupling of 2,3,4-tri-O-acetyl-alpha-L-xylopyranosyl bromide with the tetrasaccharide, allyl 4-O-{3-O-[4-O-(3,4-di-O-benzoyl-alpha-L-rhamnopyranosyl)-2,3,6-tri-O-benzoyl-alpha-D-mannopyranosyl]-4-benzoyl-alpha-L-rhamnopranosyl}-2,3,6-tri-O-benzoyl-alpha-D-mannopyranoside (18) by the Koenigs-Knorr method followed by deacylation. Compound 18 was readily prepared from the coupling of the disaccharide trichloroacetimidate, 4-O-(2-O-acetyl-3,4-di-O-benzoyl-alpha-L-rhamnopyranosyl)-2,3,6-tri-O-benzoyl-alpha-D-mannopyranosyl trichloroacetimidate (8) with the disaccharide acceptor, allyl 4-O-(2-O-acetyl-4-O-benzoyl-alpha-L-rhamnopyranosyl)-2,3,6-tri-O-benzoyl-alpha-D-mannopyranoside (16), and both 8 and 16 were prepared via the trichloroacetimidate method from simple starting materials. The sole use of acyl protecting groups substantially simplified protection and deprotection, and the allyl group at the reducing end of allyl 4-O-{2-O[2,3,4-tri-O-acetyl-beta-L-xylopyranosyl]-3-O-[4-O-(2-O-(2,3,4-tri-O-acetyl-beta-L-rhamnopyranosyl)-3,4-di-O-benzoyl-alpha-L-rhamnopyranosyl)-2,3,6-tri-O-benzoyl-alpha-D-mannopyranosyl]-4-O-benzoyl-alpha-L-rhamnopyranosyl} -2,3,6-tri-O-benzoyl-alpha-D-mannopyranoside 19 allowed further chemical transformation. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(99)00004-x
• 作为产物：
  描述：

  allyl 2,3,6-tri-O-benzoyl-α-D-mannopyranoside 在 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 palladium dichloride 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 1.67h， 生成 4-O-(2-O-acetyl-3,4-di-O-benzoyl-α-L-rhamnopyranosyl)-2,3,6-tri-O-benzoyl-α-D-mannopyranosyl trichloroacetimidate
  参考文献：
  名称：

  A highly efficient and convergent synthesis of a hexasaccharide, a dimer of the repeating unit of the antigen O2 polysaccharide of Stenotrophomonas maltophilia

  摘要：

  A highly efficient and convergent synthesis of a hexasaccharide, which is a dimer of the repeating unit of the antigen O2 polysaccharide of Stenotrophomonas maltophilia, was achieved via coupling of 2,3,4-tri-O-acetyl-alpha-L-xylopyranosyl bromide with the tetrasaccharide, allyl 4-O-{3-O-[4-O-(3,4-di-O-benzoyl-alpha-L-rhamnopyranosyl)-2,3,6-tri-O-benzoyl-alpha-D-mannopyranosyl]-4-benzoyl-alpha-L-rhamnopranosyl}-2,3,6-tri-O-benzoyl-alpha-D-mannopyranoside (18) by the Koenigs-Knorr method followed by deacylation. Compound 18 was readily prepared from the coupling of the disaccharide trichloroacetimidate, 4-O-(2-O-acetyl-3,4-di-O-benzoyl-alpha-L-rhamnopyranosyl)-2,3,6-tri-O-benzoyl-alpha-D-mannopyranosyl trichloroacetimidate (8) with the disaccharide acceptor, allyl 4-O-(2-O-acetyl-4-O-benzoyl-alpha-L-rhamnopyranosyl)-2,3,6-tri-O-benzoyl-alpha-D-mannopyranoside (16), and both 8 and 16 were prepared via the trichloroacetimidate method from simple starting materials. The sole use of acyl protecting groups substantially simplified protection and deprotection, and the allyl group at the reducing end of allyl 4-O-{2-O[2,3,4-tri-O-acetyl-beta-L-xylopyranosyl]-3-O-[4-O-(2-O-(2,3,4-tri-O-acetyl-beta-L-rhamnopyranosyl)-3,4-di-O-benzoyl-alpha-L-rhamnopyranosyl)-2,3,6-tri-O-benzoyl-alpha-D-mannopyranosyl]-4-O-benzoyl-alpha-L-rhamnopyranosyl} -2,3,6-tri-O-benzoyl-alpha-D-mannopyranoside 19 allowed further chemical transformation. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(99)00004-x