2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl-(1-> 3)-2,4,6-tri-O-benzoyl-α-D-mannopyranosyl trichloroacetimidate | 500217-09-4

• 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-> 3)-2,4,6-tri-O-benzoyl-α-D-mannopyranosyl trichloroacetimidate
• 英文别名: Bz(-2)[Bz(-3)][Bz(-4)][Bz(-6)]Man(a1-3)[Bz(-2)][Bz(-4)][Bz(-6)]Man(a)-O-C(NH)CCl3；[(2R,3R,4S,5S,6R)-3,4,5-tribenzoyloxy-6-[(2R,3R,4S,5S,6R)-3,5-dibenzoyloxy-2-(benzoyloxymethyl)-6-(2,2,2-trichloroethanimidoyl)oxyoxan-4-yl]oxyoxan-2-yl]methyl benzoate
• CAS: 500217-09-4
• 化学式: C₆₃H₅₀Cl₃NO₁₈
• 分子量: 1215.44
• InChiKey: ZHHAKHWAHNGDAJ-NLMRDXRFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.9
• 重原子数：
  85
• 可旋转键数：
  27
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.21
• 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：

  2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl-(1-> 3)-2,4,6-tri-O-benzoyl-α-D-mannopyranosyl trichloroacetimidate 、 allyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl-(1->3)-4,6-di-O-benzoyl-α-D-mannopyranoside 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以75%的产率得到allyl 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl-(1->3)-2,4,6-tri-O-benzoyl-α-D-mannopyranosyl-(1->2)-[2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl-(1->3)]-4,6-di-O-benzoyl-α-D-mannopyranoside
  参考文献：
  名称：

  A practical synthesis of α-d-Manp-(1→3)-α-d-Manp-(1→2)-[α-d-Glcp-(1→3)]-α-d-Manp-(1→2)-α-d-Manp-(1→2)-α-d-Manp, an O-specific heterohexasaccharide fragment of Citrobacter braakii O7a, 3b, 1c

  摘要：

  An O-specific heterohexasaccharide fragment of Citrobacter braakii O7a, 3b, 1c, alpha-D-Manp-(1-->3)-alpha-D-Manp-(1-->2)-[alpha-D-Glcp(1-->3)] alpha-D-Manp-(1-->2)-alpha-D-Manp-(1-->2)-alpha-D-Manp was synthesized as its methyl glycoside. Acetylation of allyl 4,6-O-benzylidene-alpha-D-mannopyranoside, followed by debenzylidenization and benzoylation gave allyl 2,3-di-O-acetyl-4,6-di-O-benzoyl-alpha-D-mannopyranoside (3), and subsequent deacetylation of 3 with CH3COCl-MeOH gave the monosaccharide acceptor 4. Condensation of isopropyl 2,3,4,6-tetra-O-benzyl-1-thio-beta-D-glucopyranoside (6) with 4 selectively afforded the alpha-(l-->3)-linked disaccharide 7. Condensation of 7 with the (1-->3)-linked disaccharide donor 9, followed by deallylation and trichloroacetimidation, afforded the tetrasaccharide donor 12. Coupling of 12 with disaccharide acceptor 13, followed by debenzylation and deacylation, furnished the target heterohexasaccharide 16. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(03)00381-1
• 作为产物：
  描述：

  p-methoxyphenyl 3-O-allyl-α-D-mannopyranoside 在 palladium dichloride 吡啶 、 ammonium cerium(IV) nitrate 、 三氟甲磺酸三甲基硅酯 、 potassium carbonate 作用下， 以 甲醇 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 3.5h， 生成 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl-(1-> 3)-2,4,6-tri-O-benzoyl-α-D-mannopyranosyl trichloroacetimidate
  参考文献：
  名称：

  α-（1→3）-连接的六氢己酸和甘露聚糖的高效实用合成

  摘要：

  α-（1→3）-连接的甘露六糖和甘露糖八糖作为其甲基糖苷是由相应的α-（1→3）-连接的二-（9）和四糖供体（21）与四糖受体（23）缩合而合成的分别进行脱酰作用。分别通过激活四糖20的C-1和四糖22的脱甲酰作用容易地制备供体21和受体23。通过将9与11偶联获得的19的1-Op-甲氧基苯基的氧化裂解制备四糖20。通过供体13与受体18的缩合获得四糖22。这些二糖9、11、13 ，使用对甲氧基苯基3-O-烯丙基-α-d-甘露吡喃糖苷（1）和2,3,4通过简单的化学转化即可轻松制得18和

  DOI：

  10.1081/car-120014899

文献信息

• Synthesis of a mannose heptasaccharide existing in baker's yeast, Saccharomyces cerevisiae X2180-1A wild-type strain
  作者：Youlin Zeng、Jianjun Zhang、Jun Ning、Fanzuo Kong

  DOI：10.1016/s0008-6215(02)00402-0

  日期：2003.1

  A mannose heptasaccharide existing in baker's yeast, Saccharomyces cerevisiae X2180-1A wild-type strain, was effectively synthesized as its allyl glycoside via TMSOTf-promoted condensation of a disaccharide donor 13 with a pentasaccharide acceptor 12, followed by deprotection. The pentasaccharide 12 was constructed by coupling of 2,3,4,6-tetra-O-benzoyl-alpha-D-mannopyranosyl-(1-->3)-2,4,6-tri-O-benzoyl-alpha-D-mannopyranosyl-(1-->2)-3,4,6-tri-O-benzoyl-alpha-D-mannopyranosyl-(1-->2)-3,4,6-tri-O-benzoyl-alpha-D-mannopyranosyl trichioroacetimidate (9) with allyl 6-O-acetyl-3,4-di-O-benzoyl-alpha-D-mannopyranoside (10), followed by deacetylation. The tetrasaccharide 9 was obtained by coupling of 2,3,4,6-tetra-O-benzoyl-alpha-D-mannopyranosyl-(1 --> 3)-2,4,6-tri-O-benzoyl-alpha-D-mannopyranosyl trichloroacetimidate (5) with allyl 3,4,6-tri-O-benzoyl-a-D-mannopyranosyl-(1-->2)-3,4,6-tri-O-benzoyl-alpha-D-mannopyranoside (6), followed by deallylation and trichloroacetimidation. The disaccharides 6 and 13 were readily obtained by known methods. (C) 2002 Elsevier Science Ltd. All rights reserved.
• AN EFFICIENT AND PRACTICAL SYNTHESIS OF α-(1→3)-LINKED MANNOHEXAOSE AND MANNOOCTAOSE
  作者：Langqiu Chen、Fanzuo Kong

  DOI：10.1081/car-120014899

  日期：2002.1.10

  tetrasaccharide 22, respectively. The tetrasaccharide 20 was prepared from oxidative cleavage of 1-O-p-methoxyphenyl of 19, which was obtained from coupling of 9 with 11. The tetrasaccharide 22 was obtained from condensation of the donor 13 with the acceptor 18. These disaccharides 9, 11, 13, and 18 were produced easily by simple chemical transformation using p-methoxyphenyl 3-O-allyl-α-d-mannopyranoside (1) and

  α-（1→3）-连接的甘露六糖和甘露糖八糖作为其甲基糖苷是由相应的α-（1→3）-连接的二-（9）和四糖供体（21）与四糖受体（23）缩合而合成的分别进行脱酰作用。分别通过激活四糖20的C-1和四糖22的脱甲酰作用容易地制备供体21和受体23。通过将9与11偶联获得的19的1-Op-甲氧基苯基的氧化裂解制备四糖20。通过供体13与受体18的缩合获得四糖22。这些二糖9、11、13 ，使用对甲氧基苯基3-O-烯丙基-α-d-甘露吡喃糖苷（1）和2,3,4通过简单的化学转化即可轻松制得18和
• A practical synthesis of α-d-Manp-(1→3)-α-d-Manp-(1→2)-[α-d-Glcp-(1→3)]-α-d-Manp-(1→2)-α-d-Manp-(1→2)-α-d-Manp, an O-specific heterohexasaccharide fragment of Citrobacter braakii O7a, 3b, 1c
  作者：Langqiu Chen、Fanzuo Kong

  DOI：10.1016/s0008-6215(03)00381-1

  日期：2003.10

  An O-specific heterohexasaccharide fragment of Citrobacter braakii O7a, 3b, 1c, alpha-D-Manp-(1-->3)-alpha-D-Manp-(1-->2)-[alpha-D-Glcp(1-->3)] alpha-D-Manp-(1-->2)-alpha-D-Manp-(1-->2)-alpha-D-Manp was synthesized as its methyl glycoside. Acetylation of allyl 4,6-O-benzylidene-alpha-D-mannopyranoside, followed by debenzylidenization and benzoylation gave allyl 2,3-di-O-acetyl-4,6-di-O-benzoyl-alpha-D-mannopyranoside (3), and subsequent deacetylation of 3 with CH3COCl-MeOH gave the monosaccharide acceptor 4. Condensation of isopropyl 2,3,4,6-tetra-O-benzyl-1-thio-beta-D-glucopyranoside (6) with 4 selectively afforded the alpha-(l-->3)-linked disaccharide 7. Condensation of 7 with the (1-->3)-linked disaccharide donor 9, followed by deallylation and trichloroacetimidation, afforded the tetrasaccharide donor 12. Coupling of 12 with disaccharide acceptor 13, followed by debenzylation and deacylation, furnished the target heterohexasaccharide 16. (C) 2003 Elsevier Ltd. All rights reserved.