2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1->3)-[2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1->6)]-2,4-di-O-acetyl-α-D-glucopyranosyl trichloroacetimidate | 331969-96-1

• 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-β-D-glucopyranosyl-(1->3)-[2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1->6)]-2,4-di-O-acetyl-α-D-glucopyranosyl trichloroacetimidate
• 英文别名: 2,4-di-O-acetyl-3,6-di-O-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-α-D-glucopyranosyl trichloroacetimidate；Bz(-2)[Bz(-3)][Bz(-4)][Bz(-6)]Glc(b1-3)[Bz(-2)[Bz(-3)][Bz(-4)][Bz(-6)]Glc(b1-6)]Glc2Ac4Ac(a)-O-C(NH)CCl3；[(2R,3R,4S,5R,6R)-3,4,5-tribenzoyloxy-6-[[(2R,3R,4S,5R,6R)-3,5-diacetyloxy-4-[(2S,3R,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: 331969-96-1
• 化学式: C₈₀H₆₈Cl₃NO₂₆
• 分子量: 1565.77
• InChiKey: GUJRIWMNBWQUCJ-VYUMTQGNSA-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：

  2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1->3)-[2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1->6)]-2,4-di-O-acetyl-α-D-glucopyranosyl trichloroacetimidate 、 4-methoxyphenyl 2,4,6-tri-O-acetyl-β-D-glucopyranosyl-(1->3)-[2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1->6)]-2.4-di-O-acetyl-β-D-glucopyranoside 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73.4%的产率得到
  参考文献：
  名称：

  Synthesis of β-(1→6)-branched (1→3)-glucododecaose and -glucopentadecaose with alternate β- and α-bonds in the backbone

  摘要：

  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)]-alpha-D-Glcp-(1-->3)}(2-3)-beta-D-Glcp-(1-->3) -[beta-D-Glcp-(1-->6)]-beta-D-Glcp were synthesized as their methoxyphenyl glycosides in a concise way with a trisaccharide as the building block. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(03)00354-9
• 作为产物：
  描述：

  三氯乙腈 、 isopropyl 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1-> 3)-[2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1-> 6)]-2,4-di-O-acetyl-1-thio-β-D-glucopyranoside 在 N-溴代丁二酰亚胺(NBS) 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 、 水 为溶剂， 以73%的产率得到2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1->3)-[2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1->6)]-2,4-di-O-acetyl-α-D-glucopyranosyl trichloroacetimidate
  参考文献：
  名称：

  天然β-d-（1→3）-吡喃葡萄糖基寡糖的合成

  摘要：

  摘要有效合成了与裂褶多糖，表葡聚糖和香菇多糖对应的β-d-（1→3）-葡聚糖核心结构衍生物。发现4，6-O-苯甲酰化的吡喃葡萄糖基受体有助于尝试形成β-d-（1→3）键。在初步小鼠试验中，表葡聚糖五糖显示出弱的抗肿瘤活性。

  DOI：

  10.1016/s0008-6215(02)00276-8

文献信息

• A general strategy for the synthesis of 3,6-branched gluco-oligosaccharides: facile synthesis of the phytoalexin elicitor oligosaccharides
  作者：Jun Ning、Yuetao Yi、Fanzuo Kong

  DOI：10.1016/s0040-4039(02)01143-7

  日期：2002.8

  A general method for the synthesis of 3,6-branched gluco-oligosaccharides has been developed. As a typical example of the method, the synthesis of the glucohexatose phytoalexin elicitor on a large scale was achieved via coupling of a trisaccharide donor with a trisaccharide acceptor. The donor and acceptor were prepared easily from 1,2:5,6-di-O-isopropylidene-α-d-glucofuranose, 2,3,4,6-tetra-O-ben

  已经开发了合成3，6-支链葡萄糖寡糖的通用方法。作为该方法的典型实例，通过三糖供体与三糖受体的偶联来大规模合成葡萄糖己糖植物抗毒素。供体和受体可以容易地由1,2：5,6-二-O-异亚丙基-α-d-呋喃呋喃糖，2,3,4,6-四-O-苯甲酰基-α-d-吡喃葡萄糖基三氯乙酰亚胺酸酯和以区域和立体选择性的方式，6 - O-乙酰基-2,3,4-三-O-苯甲酰基-α-d-吡喃葡萄糖基三氯乙酰亚胺酸酯。通过该策略也已经容易地合成了引发剂的高级寡糖，包括七，九，九，十二和十四糖。
• Highly Efficient Syntheses of the Phytoalexin-Elicitor Active<b>β</b>-(1→3)-Branched­<b>β</b>-(1→6)-Linked Heptaglucose and Its Dodecyl Glycoside
  作者：Jun Ning、Yuetao Yi、Zhongxuan Zhou、Fanzuo Kong、Jianqiang Li

  DOI：10.1055/s-2003-37644

  日期：——

  trichloroacetimidate through a regio- and stereoselective manner. The β-(1→3)-branched β-(1→6)-linked heptaglucose 1 and its dodecyl glycoside 2 having phytoalexin-elicitor activity were prepared using the developed strategy. Bioassays showed that the phytoalexin-elicitor activity of the dodecyl β-(1→3)-branched β-(1→6)-linked hexaglucoside 2 is slightly more than that of the corresponding reducing end free heptaglucose

  采用 1,2:5,6-二-O-异亚丙基-α-D-呋喃葡萄糖、2,3,4,6-四O-苯甲酰基-α-D-吡喃葡萄糖基三氯乙酰亚胺酯和6-O-乙酰基-2,3,4-三-O-苯甲酰基-α-D-吡喃葡萄糖基三氯乙酰亚胺酯通过区域选择性和立体选择性方式进行。使用开发的策略制备了具有植物抗毒素诱导剂活性的β-(1→3)-支链β-(1→6)-连接的七葡萄糖1及其十二烷基糖苷2。生物测定表明，十二烷基 β-(1→3)-支链 β-(1→6)-连接的六葡萄糖苷 2 的植物抗毒素诱导剂活性略高于相应的还原端游离七葡萄糖 1。
• Synthesis of two isomeric pentasaccharides, the possible repeating unit of the β-glucan from the micro fungus Epicoccum nigrum Ehrenb. ex Schlecht
  作者：Ying Zeng、Wenhui Zhang、Jun Ning、Fanzuo Kong

  DOI：10.1016/s0008-6215(02)00317-8

  日期：2002.11

  ta-D-Glcp-(1-->3)-beta-D-Glcp-(1-->6)]-beta-D-Glcp (II), the possible repeating unit of the beta-glucan from the micro fungus Epicoccum nigrum Ehrenb. ex Schlecht, were synthesized as their 4-methoxyphenyl glycosides in a regio- and stereoselective manner. The pentasaccharide I was obtained from 3-O-selective glycosylation of 4-methoxyphenyl 4,6-O-benzylidene-beta-D-glucopyranoside (12) with 2,3,4

  两个同分异构的五糖β-D-Glcp-（1-> 3）-[β-D-Glcp-（1-> 6）]-beta-D-Glcp-（1-> 3）-[beta -D-Glcp-（1-> 6）]-beta-D-Glcp（I）和beta-D-Glcp-（1-> 6）-beta-D-Glcp-（1-> 3） -[β-D-Glcp-（1-> 3）-β-D-Glcp-（1-> 6）]-β-D-Glcp（II），可能是来自微型真菌Epicoccum nigrum Ehrenb。如Schlecht，以区域和立体选择性的方式合成它们的4-甲氧基苯基糖苷。由4-甲氧基苯基4,6-O-亚苄基-β-D-吡喃葡萄糖苷（12）与2,3,4,6-四-O-苯甲酰基-β-D的3-O-选择性糖基化反应获得五糖I -吡喃葡萄糖基-（1-> 3）-[2,3,4,6-四-O-苯甲酰基-β-D-吡喃葡萄糖基-（1-> 6）]-2,4-二-O-乙酰基
• Unexpected α-stereochemical outcomes of attempted β-glycosylations
  作者：Feng Yang、Hongmei He、Yuguo Du、Mujian Lü

  DOI：10.1016/s0008-6215(02)00122-2

  日期：2002.7

  an effort to prepare complex oligosaccharide derivatives, a series of unexpected a glycosides were predominantly formed in the presence of neighboring group participation using imidates or thioglycosides as glycosyl donors under standard glycosylation conditions. The observations are especially suitable in the case of alpha-(1-->3) glycosidic bond formation. (C) 2002 Elsevier Science Ltd. All rights

  为了制备复杂的寡糖衍生物，在标准糖基化条件下，使用酰亚胺或硫代糖苷作为糖基供体，在邻近基团参与的情况下，主要形成了一系列意想不到的α-糖苷。该观察特别适用于α-（1-> 3）糖苷键形成的情况。（C）2002 Elsevier Science Ltd.保留所有权利。
• Silver Triflate. A Mild Alternative Catalyst for Glycosylation Conditions Using Trichloroacetimidates as Glycosyl Donors
  作者：Guohua Wei、Guofeng Gu、Yuguo Du

  DOI：10.1081/car-120025325

  日期：2003.1.10

  Although trimethylsilyl triflate (TMSOTf) has been widely used to promote glycosyl trichloroacetimidates in oligosaccharide synthesis, silver triflate (AgOTf) was proved to be a mild and in some cases more efficient catalyst in TMSOTf-sensitive glycosylations. Migration and degradation in some specific coupling reactions can be reduced significantly under this alternative glycosylation condition.