2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1->3)-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose | 150412-78-5

• 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: 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1->3)-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose
• 英文别名: 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1->6)-1,2:5,6-di-O-isopropylidene-α-D-glucopyranose；(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-(1→3)-1,2:5,6-di-O-diisopropylidene-α-D-glucofuranose；[(2R,3R,4S,5R,6S)-6-[[(3aR,5R,6S,6aR)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-yl]oxy]-3,4,5-tribenzoyloxyoxan-2-yl]methyl benzoate
• CAS: 150412-78-5
• 化学式: C₄₆H₄₆O₁₅
• 分子量: 838.862
• InChiKey: LQFYHQFHYMJIGQ-FNHAONJQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  61
• 可旋转键数：
  16
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  170
• 氢给体数：
  0
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1->3)-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 在 溶剂黄146 作用下， 反应 20.0h， 以100%的产率得到2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1->3)-1,2-O-isopropylidene-α-D-glucofuranose
  参考文献：
  名称：

  合成3,6-支链葡萄糖寡糖的一般策略：合成植物抗毒素激动剂寡糖

  摘要：

  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。

  DOI：

  10.1016/s0040-4039(02)01143-7
• 作为产物：
  描述：

  1,2,3,4,6-戊-O-苯甲酰基-D-吡喃葡萄糖苷 在 三氟甲磺酸三甲基硅酯 、 氨 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 39.0h， 生成 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1->3)-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose
  参考文献：
  名称：

  Phytoalexin-Elicitor Active β-(1→3)-Branched β-(1→6)-连接七葡萄糖及其十二烷基糖苷的高效合成

  摘要：

  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。

  DOI：

  10.1055/s-2003-37644

文献信息

• Gold(I)-Catalyzed Glycosylation with Glycosyl Ynenoates as Donors
  作者：Xiaona Li、Chenyu Li、Rongkun Liu、Jiazhe Wang、Zixuan Wang、Yan Chen、You Yang

  DOI：10.1021/acs.orglett.9b03851

  日期：2019.12.6

  A simple and versatile glycosylation method with both armed and disarmed glycosyl ynenoates as donors is developed. Employing a gold(I) complex as catalyst with or without the assistance of TfOH, the scope of the present glycosylation protocol is very wide. The utility of the present ynenoate donors is demonstrated in the efficient synthesis of oligosaccharides via the latent-active strategy and the

  开发了一种简单且通用的糖基化方法，其中武装和解除武装的糖基炔诺酸酯都作为供体。在有或没有TfOH的辅助下采用金（I）配合物作为催化剂，本糖基化方案的范围非常宽。通过潜在的活性策略和多重正交一锅策略在低聚糖的有效合成中证明了本发明的炔酸供体的实用性。最后，该方法能够正式合成肺炎链球菌血清型3的四糖半抗原和32mer聚甘露糖苷的高度收敛合成。
• 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
• HClO4–SiO2 catalyzed glycosylation using sugar trichloroacetimidates as glycosyl donors
  作者：Yuguo Du、Guohua Wei、Shuihong Cheng、Yuxia Hua、Robert J. Linhardt

  DOI：10.1016/j.tetlet.2005.11.025

  日期：2006.1

  Silica-supported perchloric acid (HClO4-SiO2) has been used as an efficient promoter,, as a replacement of TMSOTf, in various glycosylation reactions using sugar trichloroacetimidates as glycosyl donors. Operational simplicity, economic considerations, high yield, short reaction time and low toxicity were the key features associated with this protocol. (c) 2005 Elsevier Ltd. All rights reserved.
• Synthesis of β-(1→6)-branched β-(1→3) glucohexaose and its analogues containing an α-(1→3) linked bond with antitumor activity
  作者：Jun Ning、Wenhui Zhang、Yuetao Yi、Guangbin Yang、Zhikui Wu、Jie Yi、Fanzuo Kong

  DOI：10.1016/s0968-0896(03)00118-4

  日期：2003.5

  A beta-(1 --> 6)-branched beta-(1 --> 3)-glucohexaose, present in many biologically active polysaccharides from traditionally herbal medicines such as Ganoderma lucidum, Schizophyllum commune and Lentinus edodes, was synthesized as its lauryl glycoside 32, and its analogues 18, 20 and 33 containing an alpha-(l --> 3) linked bond were synthesized. It is interesting to find that coupling of a 3,6-branched acylated trisaccharide trichloroacetimidate donor 9 with 3,6-branched acceptors 13 and 16 with 3'-OH gave the alpha-(1 --> 3)linked hexasaccharides 17 and 19, respectively, in spite of the presence of C-2 ester capable of neighboring group participation. However, coupling of 9 with 4-methoxyphenyl 4,6-0-benzylidene-beta-D-glucopyranoside (27) selectively gave beta-(1 --> 3)-linked tetrasaccharide 28. Simple chemical transformation of the tetrasaccharide 28 gave acylated tetrasaccharide trichloroacetimidate 29. Coupling of 29 with lauryl (I --> 6)-linked disaccharide 26 with 3-OH gave beta-(I --> 3)-linked hexasaccharide 30 as the major product. Bioassay showed that in combination with the chemotherapeutic agent cyclophospamide (CPA), the hexaose 18 at a dose of 0.5-1 mg/kg substantially increased the inhibition of S 180 for CPA, but decreased the toxicity caused by CPA. Some of these oligosaccharides also inhibited U-14 noumenal tumor in mice effectively. (C) 2003 Elsevier Science Ltd. All rights reserved.
• A novel method for activation of thioglycosides, combination of N-bromosuccinimide and triflic acid salts
  作者：Fukase Koichi、Hasuoka Atsushi、Kusumoto Shoichi

  DOI：10.1016/s0040-4039(00)60378-7

  日期：1993.3