2-O-acetyl-3,4,6-tri-O-benzoyl-α-D-mannopyranosyl-(1-> 2)-3,4,6-tri-O-benzoyl-α-D-mannopyranosyl trichloroacetimidate | 324041-20-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-O-acetyl-3,4,6-tri-O-benzoyl-α-D-mannopyranosyl-(1-> 2)-3,4,6-tri-O-benzoyl-α-D-mannopyranosyl trichloroacetimidate
• 英文别名: 2-O-acetyl-3,4,6-tri-O-benzoyl-α-D-mannopyranosyl-(1->2)-3,4,6-tri-O-benzoyl-α-D-mannopyranosyl trichloroacetimidate；2-O-Acetyl-3,4,6-tri-O-benzoyl-α-D-mannopyranosyl-(1->2)-3,4,6-tri-O-benzoyl-α-D-mannopyranosyl trichloroimidate；Bz(-3)[Bz(-4)][Bz(-6)]Man2Ac(a1-2)[Bz(-3)][Bz(-4)][Bz(-6)]Man(a)-O-C(NH)CCl3；[(2R,3R,4S,5S,6R)-5-[(2R,3S,4S,5R,6R)-3-acetyloxy-4,5-dibenzoyloxy-6-(benzoyloxymethyl)oxan-2-yl]oxy-3,4-dibenzoyloxy-6-(2,2,2-trichloroethanimidoyl)oxyoxan-2-yl]methyl benzoate
• CAS: 324041-20-5
• 化学式: C₅₈H₄₈Cl₃NO₁₈
• 分子量: 1153.37
• InChiKey: ZTCOBTVTWYNDSC-BBHXIMPSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.2
• 重原子数：
  80
• 可旋转键数：
  26
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  245
• 氢给体数：
  1
• 氢受体数：
  19

反应信息

• 作为反应物：
  描述：

  2-O-acetyl-3,4,6-tri-O-benzoyl-α-D-mannopyranosyl-(1-> 2)-3,4,6-tri-O-benzoyl-α-D-mannopyranosyl trichloroacetimidate 在 三氟甲磺酸三甲基硅酯 作用下， 以 吡啶 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 allyl 2-O-acetyl-3,4,6-tri-O-benzoyl-α-D-mannopyranosyl-(1->2)-3,4,6-tri-O-benzoyl-α-D-mannopyranosyl-(1->3)-2-O-acetyl-4,6-O-benzylidene-α-D-mannopyranoside
  参考文献：
  名称：

  人CD2和甘露糖六糖抗原因子13b中N-聚糖的甘露糖八糖的快速区域选择性和立体选择性合成

  摘要：

  通过TMSOTf促进三糖4,6-二醇受体与五糖供体的选择性6-糖基化，然后脱保护，实现了在人CD2粘附域中N-连接聚糖的甘露糖八糖的高度简洁和有效的合成。 。通过用2-O-乙酰基-3,4,6-三-O-苯甲酰基-α-D-甘露吡喃糖基-对1,2-O-亚乙基-β-D-甘露吡喃糖进行选择性3,6-二糖基化来构建五糖。 （1-> 2）-3,4,6-三-O-苯甲酰基-α-D-甘露吡喃糖基三氯乙酰亚胺酸酯，而三糖是通过烯丙基4,6-O-亚苄基-α的选择性3-O-糖基化获得的-D-甘露吡喃糖苷与相同的二糖三氯乙酰亚胺酸酯，然后进行脱苄基作用。甘露糖六糖抗原因子13b是通过三糖供体2-O-乙酰-3,4，

  DOI：

  10.1016/s0008-6215(01)00307-x
• 作为产物：
  描述：

  3,4,6-tri-O-benzoyl-α-D-mannopyranose 1,2-(allyl orthoacetate) 在 palladium dichloride 三氟甲磺酸三甲基硅酯 、 sodium acetate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 、 水 、 溶剂黄146 为溶剂， 反应 17.0h， 生成 2-O-acetyl-3,4,6-tri-O-benzoyl-α-D-mannopyranosyl-(1-> 2)-3,4,6-tri-O-benzoyl-α-D-mannopyranosyl trichloroacetimidate
  参考文献：
  名称：

  来自小孢子菌属植物的真菌细胞壁多糖的甘露糖三糖和四糖重复单元的简便合成

  摘要：

  摘要 三糖 α-D-吡喃甘露糖基-(1→2)-α-D-吡喃甘露糖基-(1→6)-α-D-吡喃甘露糖和四糖 α-D-吡喃甘露糖基-(1→2) 的简便合成-α-D-吡喃甘露糖基-(1→6)-α-D-吡喃甘露糖基-(1→6)-D-吡喃甘露糖是来自石膏小孢子菌和毛癣菌的真菌细胞壁多糖的重复单元，使用α-( 1→2)-连接的二糖亚胺酸酯作为供体。二糖亚氨酸酯由 3,4,6-tri-O-benzoyl-1,2-O-allyloxyethylidene-β-D-mannopyranose 的自缩合制备。

  DOI：

  10.1081/scc-120003613

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 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。
• Zhu; Kong, Synlett, 2000, # 12, p. 1783 - 1787
  作者：Zhu、Kong

  DOI：——

  日期：——
• Synthesis of two oligosaccharides, the GPI anchor glycans from S. cerevesiae and A. fumigatus
  作者：Zuchao Ma、Jianjun Zhang、Fanzuo Kong

  DOI：10.1016/j.carres.2003.09.030

  日期：2004.1

  Two oligosaccharides, alpha-D-Manp-(1 --> 2)-alpha-D-Manp-(1 --> 2)-alpha-D-Manp-(1 --> 6)-alpha-D-Manp-(l --> 4)-alpha-D-GlcpNAc (I) and alpha-D-Manp-(1 --> 3)-alpha-D-Manp-(1 --> 2)-alpha-D-Manp-(1 --> 2)-alpha-D-Manp-(1 --> 6)-alpha-D-Manp-(1 --> 4)-alpha-D-GlcpNAc (II), the glycosylphosphatidylinositol (GPI) anchor glycans from S. cerevesiae and A. fumigatus were synthesized as their methyl glycosides in a regio- and stereoselective manner. The pentasaccharide I was obtained from 6-O-selective glycosylation of methyl 2,3-di-O-benzoyl-alpha-D-mannopyranosyl-(l --> 4)-2-acetamido-3,6-di-O-benzoyl-2-deoxy-alpha-D-glucopyranoside (8) with 2-O-acetyl-3,4,6-tri-O-benzoyl-alpha-D-mannopyranosyl-(1 --> 2) -3,4,6-tri-O-benzoyl-alpha-D-mannopyranosyl trichloroacetimidate (9), followed by benzoylation, deacetylation, and mannosylation, and then by deprotection. The hexasaccharide (II) was obtained via condensation of allyl 3,4,6-tri-O-benzoyl-alpha-D-mannopyranosyl-(l --> 2)-3,4,6-tri-O-benzoyl-alpha-D-mannopyranoside (17) with 2,3,4,6-tetra-O-benzoyl-alpha-D-mannopyranosyl-(1 --> 3)-2,4,6-tri-O-acetyl-alpha-D-mannopyranosyl trichloroacetimidate (16), followed by deallylation, trichloroacetimidation, and coupling with acceptor (8), and finally by deprotection. (C) 2003 Elsevier Ltd. All rights reserved.