2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl-(1->3)-[2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl-(1->6)]-2,4-di-O-acetyl-α-D-glucopyranosyl trichloroacetimidate | 313220-24-5

• 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)-[2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl-(1->6)]-2,4-di-O-acetyl-α-D-glucopyranosyl trichloroacetimidate
• 英文别名: Bz(-2)[Bz(-3)][Bz(-4)][Bz(-6)]Man(a1-3)[Bz(-2)[Bz(-3)][Bz(-4)][Bz(-6)]Man(a1-6)]Glc2Ac4Ac(a)-O-C(NH)CCl3；[(2R,3R,4S,5S,6S)-3,4,5-tribenzoyloxy-6-[[(2R,3R,4S,5R,6R)-3,5-diacetyloxy-4-[(2R,3S,4S,5R,6R)-3,4,5-tribenzoyloxy-6-(benzoyloxymethyl)oxan-2-yl]oxy-6-(2,2,2-trichloroethanimidoyl)oxyoxan-2-yl]methoxy]oxan-2-yl]methyl benzoate
• CAS: 313220-24-5
• 化学式: C₈₀H₆₈Cl₃NO₂₆
• 分子量: 1565.77
• InChiKey: GUJRIWMNBWQUCJ-FDEMNFQCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14.1
• 重原子数：
  110
• 可旋转键数：
  37
• 环数：
  11.0
• sp3杂化的碳原子比例：
  0.26
• 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：

  allyl 2,3,6-tri-O-benzoyl-α-D-glucopyranoside 、 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl-(1->3)-[2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl-(1->6)]-2,4-di-O-acetyl-α-D-glucopyranosyl 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 3.0h， 以90%的产率得到allyl 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl-(1->3)-[2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl-(1->6)]-2,4-di-O-acetyl-β-D-glucopyranosyl-(1->4)-2,3,6-tri-O-benzoyl-α-D-glucopyranoside
  参考文献：
  名称：

  A facile synthesis of the tetrasaccharide repeating unit of mannoglucan from Microellobosporia grisea

  摘要：

  A facile synthesis of the tetrasaccharide repeating unit of mannoglucan from Microellobosporia grisea was achieved through coupling of 4,6-O-benzylidene-1,2-O-ethylidene-alpha-D-glucopyranose with per-O-benzoylated mannopyranosyl trichloroacetimidate, followed by debenzylidenation, selective 6-O-mannopyranosylation, then hydrolysis of the 1,2-O-ethylidene group, 1,2-O-acetylation and conversion to the 1-trichloroacetimidate, and subsequent condensation of the activated trisaccharide with allyl 2,3,6-tri-0-benzoyl-alpha-D-glucopyranoside. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(00)00160-9
• 作为产物：
  描述：

  三氯乙腈 、 3,6-di-O-(2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl)-2,4-di-O-acetyl-D-glucopyranose 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 2.0h， 以90%的产率得到2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl-(1->3)-[2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl-(1->6)]-2,4-di-O-acetyl-α-D-glucopyranosyl trichloroacetimidate
  参考文献：
  名称：

  A facile synthesis of the tetrasaccharide repeating unit of mannoglucan from Microellobosporia grisea

  摘要：

  A facile synthesis of the tetrasaccharide repeating unit of mannoglucan from Microellobosporia grisea was achieved through coupling of 4,6-O-benzylidene-1,2-O-ethylidene-alpha-D-glucopyranose with per-O-benzoylated mannopyranosyl trichloroacetimidate, followed by debenzylidenation, selective 6-O-mannopyranosylation, then hydrolysis of the 1,2-O-ethylidene group, 1,2-O-acetylation and conversion to the 1-trichloroacetimidate, and subsequent condensation of the activated trisaccharide with allyl 2,3,6-tri-0-benzoyl-alpha-D-glucopyranoside. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(00)00160-9

文献信息

• Synthesis of mannose-containing analogues of (1→6)-branched (1→3)-glucohexaose (I)
  作者：Zicheng Wu、Fanzuo Kong

  DOI：10.1016/s0008-6215(03)00263-5

  日期：2003.8

  alpha-D-Manp-(1-->3)-[alpha-D-Manp-(1-->6)]-alpha-D-Glcp-(1-->3)-beta-D-Glcp-(1-->3)-[alpha-D-Manp-(1-->6)]-D-Glcp and alpha-D-Manp-(1-->3)-[beta-D-Glcp-(1-->6)]-alpha-D-Glcp-(1-->3)-beta-D-Glcp-(1-->3)[-alpha-D-Manp-(1-->6)]-D-Glcp were synthesized in a regio- and stereoselective way as the mannose-containing analogues of the immunomodulating beta-D-Glcp-(1-->3)-[beta-D-Glcp-(1-->6)]-alpha-D-Glcp-(1-->3)-beta-D-Glcp-(1 -->3)-[beta-D-Glcp-(1-->6)]-D-Glcp. (C) 2003 Elsevier Ltd. All rights reserved.
• Synthesis of mannose-containing analogues of (1→6)-branched (1→3)-glucohexaose
  作者：Zicheng Wu、Fanzuo Kong

  DOI：10.1016/j.carres.2003.10.015

  日期：2004.1

  Coupling of the trisaccharide acceptor 2,4,6-tri-O-acetyl-beta-D-glucopyranosyl-(1 --> 3)-[2,3,4,6-tetra-O-benzoyl-beta-D-glucopyranosyl-(1 --> 6)]-5-O-acetyl-1,2-O-isopropylidene-alpha-D-glucofuranose (2) with the trisaccharide donor 2,3,4,6-tetra-O-benzoyl-alpha-D-annopyranosyl-(1 --> 3)-[2,3,4,6-tetra-O-benzoyl-beta-D-glucopyranosyl-(1 --> 6)]-2,4-di-O-acetyl-alpha-D-glucopyranosyl trichloroacetimidate (1) gave an alpha-linked hexasaccharide 3, while coupling of 2 with the trisaccharide donor 2,3,4,6-tetra-O-benzoyla-D-mannopyranosyl-(1 -4 3)-[2,3,4,6-tetra-O-benzoyl-alpha-D-mannopyranosyl-(1 --> 6)]-2,4-di-O-acetyl-alpha-D-glucopyranosyl trichloroacetimidate (7) produced alpha-8 and beta-linked 12 hexasaccharides in a ratio of 3:2. Deprotection of 3, 8, and 12 afforded the analogues of the immunomodulator beta-D-Glcp-(1 --> 3)-[beta-D-Glcp-(1 --> 6)]-alpha-D-Glcp-(1 --> 3)-(beta-D-Glcp-(1 --> 3)-[beta-D-Glcp-(1 --> 6)]-D-Glcp (A). (C) 2003 Elsevier Ltd. All rights reserved.