2,3,4,6-Tetra-O-benzoyl-α-D-mannopyranosyl-(1->2)-3,4,6-tri-O-benzoyl-α-D-mannopyranosyl-(1->2)-3,4,6-tri-O-benzoyl-α-D-mannopyranosyl trichloroimidate | 369641-41-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3,4,6-Tetra-O-benzoyl-α-D-mannopyranosyl-(1->2)-3,4,6-tri-O-benzoyl-α-D-mannopyranosyl-(1->2)-3,4,6-tri-O-benzoyl-α-D-mannopyranosyl trichloroimidate
• 英文别名: 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl-(1->2)-3,4,6-tri-O-benzoyl-α-D-mannopyranosyl-(1->2)-3,4,6-tri-O-benzoyl-α-D-mannopyranosyl trichloroacetimidate；Bz(-2)[Bz(-3)][Bz(-4)][Bz(-6)]Man(a1-2)[Bz(-3)][Bz(-4)][Bz(-6)]Man(a1-2)[Bz(-3)][Bz(-4)][Bz(-6)]Man(a)-O-C(NH)CCl3；[(2R,3R,4S,5S,6R)-3,4-dibenzoyloxy-6-[(2R,3S,4S,5R,6R)-4,5-dibenzoyloxy-6-(benzoyloxymethyl)-2-(2,2,2-trichloroethanimidoyl)oxyoxan-3-yl]oxy-5-[(2R,3S,4S,5R,6R)-3,4,5-tribenzoyloxy-6-(benzoyloxymethyl)oxan-2-yl]oxyoxan-2-yl]methyl benzoate
• CAS: 369641-41-8
• 化学式: C₉₀H₇₂Cl₃NO₂₆
• 分子量: 1689.91
• InChiKey: XUKFQGJFDOESPA-JLTMUXJTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  17.4
• 重原子数：
  120
• 可旋转键数：
  39
• 环数：
  13.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  342
• 氢给体数：
  1
• 氢受体数：
  27

反应信息

• 作为反应物：
  描述：

  2,3,4,6-Tetra-O-benzoyl-α-D-mannopyranosyl-(1->2)-3,4,6-tri-O-benzoyl-α-D-mannopyranosyl-(1->2)-3,4,6-tri-O-benzoyl-α-D-mannopyranosyl trichloroimidate 、 4,6-O-benzylidene-1,2-O-ethylidene-β-D-mannopyranose 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86%的产率得到2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl-(1->2)-3,4,6-tri-O-benzoyl-α-D-mannopyranosyl-(1->2)-3,4,6-tri-O-benzoyl-α-D-mannopyranosyl-(1->3)-4,6-O-benzylidene-1,2-O-ethylidene-β-D-mannopyranose
  参考文献：
  名称：

  N-聚糖中甘露糖三糖，四糖，五糖，六糖，七糖和八糖的高效实用合成

  摘要：

  使用简单的甘露糖基衍生物作为起始原料，实现了N-聚糖的甘露糖三糖，四糖，五糖，六糖，七糖和八糖的高效和实用的区域和立体选择性合成。

  DOI：

  10.1016/s0957-4166(02)00107-6
• 作为产物：
  描述：

  三氯乙腈 、 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl-(1->2)-3,4,6-tri-O-benzoyl-α-D-mannopyranosyl-(1->2)-3,4,6-tri-O-benzoyl-α-D-mannopyranose 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 生成 2,3,4,6-Tetra-O-benzoyl-α-D-mannopyranosyl-(1->2)-3,4,6-tri-O-benzoyl-α-D-mannopyranosyl-(1->2)-3,4,6-tri-O-benzoyl-α-D-mannopyranosyl trichloroimidate
  参考文献：
  名称：

  高效合成在 HIV 糖蛋白 gp 120 上表达的 N-聚糖的甘露糖九糖

  摘要：

  通过 TMSOTf 促进四糖-4,6-二醇受体与五糖供体的选择性 6-糖基化，然后进行脱保护，实现了表达在 HIV 蛋白 gp 120 上的甘露糖非异构体的高效简洁合成。五糖是通过 1,2-O-ethylidene-β-d-mannopyranose 与 2-O-acetyl-3,4,6-tri-O-benzoyl-α-d-mannopyranosyl-(1 → 2)-3,4,6-O-benzoyl-α-d-mannopyranosyl trichloroimidate 的选择性 3,6-二糖基化构建的，而四糖则是通过烯丙基 4,6-O-benzilidene-β-d-mannopyranose-(1 → 2)-3,4,6-O-benzoyl-α-d-mannopyranosyl trichloroimidate 的选择性 3-O-糖基化获得的、6-O-二苯甲酰基-δ-d-吡喃甘露糖苷与 2,3,4,6-四-O-苯甲酰基-δ-d-吡喃甘露糖基-(1→2)-3,4,6-三-O-苯甲酰基-δ-d-吡喃甘露糖基-(1→2)-3,4,6-三-O-苯甲酰基-δ-d-吡喃甘露糖基三氯亚氨酸酯进行选择性 3-O-糖基化反应得到四糖。

  DOI：

  10.1055/s-2001-16062

文献信息

• Highly Efficient Synthesis of the Mannose Nonasaccharide of the N-Glycan Expressed on the HIV Glycoprotein gp 120
  作者：Yuliang Zhu、Fanzuo Kong

  DOI：10.1055/s-2001-16062

  日期：——

  A highly concise and effective synthesis of the mannose nonasaccharide of the glycan expressed on the HIV protein gp 120 was achieved via TMSOTf promoted selective 6-glycosylation of a tetrasaccharide 4,6-diol acceptor with a pentasaccharide donor followed by deprotection. The pentasaccharide was constructed by selective 3,6-diglycosylation of 1,2-O-ethylidene-β-d-mannopyranose with 2-O-acetyl-3,4,6-tri-O-benzoyl-α-d-mannopyranosyl-(1 → 2)-3,4,6-O-benzoyl-α-d-mannopyranosyl trichloroimidate while the tetrasaccharide was obtained by selective 3-O-glycosylation of allyl 4,6-O-benzilidene-α-d-mannopyranoside with 2,3,4,6-tetra-O-benzoyl-α-d-mannopyranosyl-(1 → 2)-3,4,6-tri-O-benzoyl-α-d-mannopyranosyl-(1 → 2)-3,4,6-tri-O-benzoyl-α-d-mannopyranosyl trichloroimidate.

  通过 TMSOTf 促进四糖-4,6-二醇受体与五糖供体的选择性 6-糖基化，然后进行脱保护，实现了表达在 HIV 蛋白 gp 120 上的甘露糖非异构体的高效简洁合成。五糖是通过 1,2-O-ethylidene-β-d-mannopyranose 与 2-O-acetyl-3,4,6-tri-O-benzoyl-α-d-mannopyranosyl-(1 → 2)-3,4,6-O-benzoyl-α-d-mannopyranosyl trichloroimidate 的选择性 3,6-二糖基化构建的，而四糖则是通过烯丙基 4,6-O-benzilidene-β-d-mannopyranose-(1 → 2)-3,4,6-O-benzoyl-α-d-mannopyranosyl trichloroimidate 的选择性 3-O-糖基化获得的、6-O-二苯甲酰基-δ-d-吡喃甘露糖苷与 2,3,4,6-四-O-苯甲酰基-δ-d-吡喃甘露糖基-(1→2)-3,4,6-三-O-苯甲酰基-δ-d-吡喃甘露糖基-(1→2)-3,4,6-三-O-苯甲酰基-δ-d-吡喃甘露糖基三氯亚氨酸酯进行选择性 3-O-糖基化反应得到四糖。
• Synthesis of a mannose nonasaccharide existing in the exopolysaccharide of Cryphonectria parasitica
  作者：Jianjun Zhang、Zuchao Ma、Fanzuo Kong

  DOI：10.1016/s0008-6215(03)00267-2

  日期：2003.8

  alpha-D-Manp-(1-->2)-alpha-D-Manp-(1-->2)-alpha-D-Manp-(1-->6)[alpha-D-Manp-(1-->3)-alpha-D-Manp-(1-->2)-alpha-D-Manp-(1-->2)]+alpha-D-Manp-(1-->6)-[alpha-D-Manp-(1-->2)]+alpha-D-Manp, existing in the exopolysaccharide of Cryphonectria parasitica was synthesized as its allyl glycoside in a regio- and stereoselective manner. (C) 2003 Elsevier Ltd. All rights reserved.
• Synthesis of α-Manp-(1→2)-α-Manp-(1→3)-α-Manp-(1→3)-Manp, the tetrasaccharide repeating unit of Escherichia coli O9a, and α-Manp-(1→2)-α-Manp-(1→2)-α-Manp-(1→3)-α-Manp-(1→3)-Manp, the pentasaccharide repeating unit of E. coli O9 and Klebsiella O3
  作者：Langqiu Chen、Yuliang Zhu、Fanzuo Kong

  DOI：10.1016/s0008-6215(02)00011-3

  日期：2002.3

  3- O -allyl-2,4,6-tri- O -benzoyl-α- d -mannopyranosyl trichloroacetimidate ( 5 ). Condensation of 5 with methyl 4,6- O -benzylidene-α- d -mannopyranoside ( 6 ) selectively afforded the (1→3)-linked disaccharide 7 . Benzoylation of 7 , debenzylidenation, benzoylation, and deallylation gave methyl 2,4,6-tri- O -benzoyl-α- d -mannopyranosyl-(1→3)-2,4,6-tri- O -benzoyl-α- d -mannopyranoside ( 11 ) as the

  摘要大肠杆菌O9a的四糖重复单元，α-d -Man p-（1→2）-α-d -Man p-（1→3）-α-d -Man p-（1→3）-d -Man p和大肠杆菌O9和克雷伯菌O3的五糖重复单元，α-d -Man p-（1→2）-α-d-Man p-（1→2）-α-d -Man p合成了-（1→3）-α-d-Manp-（1→3）-d-Man p作为甲基糖苷。因此，对-甲氧基苯基α-d-甘露吡喃糖苷经由二丁基锡中间体的选择性3-O-烯丙基化以良好的产率得到了对-甲氧基苯基3-O-烯丙基-α-d-甘露吡喃糖苷（2）。苯甲酰化（→3），然后除去1- O-甲氧基苯基（→4），然后进行三氯乙酰亚胺化，得到3- O-烯丙基-2,4,6-三-O-苯甲酰基-α-d-甘露酰吡喃糖基三氯乙酰胺酸酯（5 ）。5与甲基4,6-O-亚苄基-α-d-甘露吡喃糖苷（6）缩合选择性地提供（1→3）-连接的二糖7。7的苄基
• Efficient and practical syntheses of mannose tri-, tetra-, penta-, hexa-, hepta-, and octasaccharides existing in N-glycans
  作者：Jianjun Zhang、Fanzuo Kong

  DOI：10.1016/s0957-4166(02)00107-6

  日期：2002.3

  An efficient and practical regio- and stereoselective synthesis of mannose tri-, tetra-, penta-, hexa-, hepta-, and octasaccharides of N-glycans was achieved using simple mannosyl derivatives as the starting materials.

  使用简单的甘露糖基衍生物作为起始原料，实现了N-聚糖的甘露糖三糖，四糖，五糖，六糖，七糖和八糖的高效和实用的区域和立体选择性合成。