2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1->3)-2,4,6-tri-O-acetyl-α-D-glucopyranosyl trichloroacetimidate | 445025-16-1

• 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)-2,4,6-tri-O-acetyl-α-D-glucopyranosyl trichloroacetimidate
• 英文别名: Bz(-2)[Bz(-3)][Bz(-4)][Bz(-6)]Glc(b1-3)Glc2Ac4Ac6Ac(a)-O-C(NH)CCl3；[(2R,3R,4S,5R,6S)-3,4,5-tribenzoyloxy-6-[(2R,3R,4S,5R,6R)-3,5-diacetyloxy-2-(acetyloxymethyl)-6-(2,2,2-trichloroethanimidoyl)oxyoxan-4-yl]oxyoxan-2-yl]methyl benzoate
• CAS: 445025-16-1
• 化学式: C₄₈H₄₄Cl₃NO₁₈
• 分子量: 1029.23
• InChiKey: VEATYKFOTHQQSB-IZLSKNEPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.9
• 重原子数：
  70
• 可旋转键数：
  24
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.33
• 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-β-D-glucopyranosyl-(1->3)-2,4,6-tri-O-acetyl-α-D-glucopyranosyl trichloroacetimidate 、 在 三氟甲磺酸三甲基硅酯 、 palladium dichloride 、 氨 作用下， 以 二氯甲烷 、 甲醇 为溶剂， 反应 168009.0h， 以52 mg的产率得到β-D-glucopyranosyl-(1->3)-β-D-glucopyranosyl-(1->3)-β-D-glucopyranosyl-(1->3)-β-D-glucopyranosyl-(1->3)-[β-D-glucopyranosyl-(1->3)-β-D-glucopyranosyl-(1->6)]-β-D-glucopyranose
  参考文献：
  名称：

  Synthesis of two heptasaccharide analogues of the lentinan repeating unit

  摘要：

  beta-D-Glcp-(1-->3)-beta-D-Glcp-(1-->3)-beta-D-Glcp-(1-->3)-beta-D-Glcp-(1-->3)-[beta-D-Glcp-(1-->3)-beta-D-Glcp-(1-->6)]-beta-D-Glcp (18) and the allyl glycoside of beta-D-Glcp-(1-->3)-[beta-D-Glcp-(1-->6)]-beta-D-Glcp-(1-->3)-beta-D-Glcp-(1-->3)-beta-D-Glcp-(1-->3)[-beta-D-Glcp-(1-->6)]-alpha-D-Glcp (29) were synthesized as the analogues of the lentinan repeating heptaose by building the pentasaccharide backbones first, followed by attaching the side chains. 4,6-O-Benzylidenated mono-13 or disaccharide 8 were used as the acceptor to ensure the beta linkage in the synthesis of 18, while 4,6-O-benzylidenated disaccharides 21 and 23 were used as the donor and acceptor, respectively, to ensure the beta linkage in the synthesis of 29. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2003.08.003
• 作为产物：
  描述：

  三氯乙腈 、 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1->3)-2,4-di-O-acetyl-α,β-D-glucopyranose 在 1,8-diaza-bicyclo[5.4.0]undecene 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以600 mg的产率得到2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1->3)-2,4,6-tri-O-acetyl-α-D-glucopyranosyl trichloroacetimidate
  参考文献：
  名称：

  两种同分异构的五糖的合成，这是来自微真菌黑短Epi的一种可能的β-葡聚糖重复单元。前Schlecht。

  摘要：

  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

  DOI：

  10.1016/s0008-6215(02)00317-8

文献信息

• 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。
• Pure α-linked products can be obtained in high yields in glycosylation with glucosyl trichloroacetimidate donors with a C2 ester capable of neighboring group participation
  作者：Ying Zeng、Jun Ning、Fanzuo Kong

  DOI：10.1016/s0040-4039(02)00584-1

  日期：2002.5

  Predominant or even pure (1-->3)-alpha-linked products can be generated in glycosylation with glucosyl trichloroacetimidate donors with a C2 ester capable of neighboring group participation. Benzoylation of either the donors or acceptors gave more beta-linkage, while 4,6-O-benzylidenation of the acceptor gave exclusive beta-glucosylation. 3-O-Glycosylation of the donor and the presence of a (1-->3)-beta-linkage in the oligosaccharide acceptor gave sole alpha-glucosylation. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Regioselective glycosylation of 4,6-O-benzylidenated glucopyranosides
  作者：Ying Zeng、Fanzuo Kong

  DOI：10.1016/s0008-6215(03)00040-5

  日期：2003.4

  Regioselective glycosylation with allyl 4,6-O-benzylidene-alpha,beta-D-glucopyrano side or methyl 4,6-O-benzylidene-alpha,beta-D-glucopyranoside as the acceptor was investigated. It was found that the regioselectivity depends upon donor size and anomeric configuration of the acceptor, i.e., with a monosaccharide donor and an a-form acceptor, the (1 --> 3)-linked product was obtained predominantly or exclusively, while with disaccharide or trisaccharide donors and either an alpha or beta form acceptor, the (1 --> 2)-linked oligosaccharides were the only products. (C) 2003 Elsevier Science Ltd. All rights reserved.