6-azido-6-deoxy-2,3,4-tri-O-benzyl-D-glucopyranose

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 6-azido-6-deoxy-2,3,4-tri-O-benzyl-D-glucopyranose
• 英文别名: (3R,4S,5R,6R)-6-(azidomethyl)-3,4,5-tris(phenylmethoxy)oxan-2-ol
• 化学式: C₂₇H₂₉N₃O₅
• 分子量: 475.544
• InChiKey: YOCNTWJRHZJXIH-MZIUKZFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  35
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  71.5
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  6-azido-6-deoxy-2,3,4-tri-O-benzyl-D-glucopyranose 在 三氟甲磺酸三甲基硅酯 、 4-甲基苯磺酸吡啶 、 sodium hydride 、 N,N'-二环己基碳二亚胺 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 38.5h， 生成 1,2-dipalmitoyl-3-O-(6'-amino-2',3',4'-tri-O-benzyl-6'-deoxy-α-D-glucosyl)-sn-glycerol
  参考文献：
  名称：

  Evaluation of potential Myt1 kinase inhibitors by TR-FRET based binding assay

  摘要：

  In the human cell cycle, the Myt1 kinase is a crucial regulator of the G2/M transition. Because this membrane-associated kinase is hard to obtain and assay, there is a distinct lack of data so far. Here we report the derivatization of a glycoglycerolipid which was shown previously to be active in a Myt1 activity assay. These compounds were tested in a binding assay together with a set of common kinase inhibitors against a full-length Myt1 expressed in a human cell line. Dasatinib exhibited nanomolar affinity whereas broad coverage inhibitors such as sunitinib and staurosporine derivatives did not show any effect. We also carried out docking studies for the most potent compounds allowing further insights into the inhibitor interaction of this kinase. The glycoglycerolipids showed no significant effects in the binding assay, endorsing the idea of a mechanism of action distant from the active site. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.06.007
• 作为产物：
  描述：

  甲基-6-O-三苯基甲基-alpha-D-吡喃葡萄糖苷 在 sodium azide 、 硫酸 、 三氟化硼乙醚 、 sodium hydride 、 溶剂黄146 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 生成 6-azido-6-deoxy-2,3,4-tri-O-benzyl-D-glucopyranose
  参考文献：
  名称：

  Evaluation of potential Myt1 kinase inhibitors by TR-FRET based binding assay

  摘要：

  In the human cell cycle, the Myt1 kinase is a crucial regulator of the G2/M transition. Because this membrane-associated kinase is hard to obtain and assay, there is a distinct lack of data so far. Here we report the derivatization of a glycoglycerolipid which was shown previously to be active in a Myt1 activity assay. These compounds were tested in a binding assay together with a set of common kinase inhibitors against a full-length Myt1 expressed in a human cell line. Dasatinib exhibited nanomolar affinity whereas broad coverage inhibitors such as sunitinib and staurosporine derivatives did not show any effect. We also carried out docking studies for the most potent compounds allowing further insights into the inhibitor interaction of this kinase. The glycoglycerolipids showed no significant effects in the binding assay, endorsing the idea of a mechanism of action distant from the active site. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.06.007

文献信息

• Synthesis and Conformational Studies of Peptidomimetics Containing Furanoid Sugar Amino Acids and a Sugar Diacid
  作者：T. K. Chakraborty、S. Ghosh、S. Jayaprakash、J. A. R. P. Sharma、V. Ravikanth、P. V. Diwan、R. Nagaraj、A. C. Kunwar

  DOI：10.1021/jo000408e

  日期：2000.10.1

  Incorporation of these furanoid sugar amino acids into Leu-enkephalin replacing its Gly-Gly portion gave analogues 8-11. Detailed structural analysis of these molecules by circular dichroism (CD) and various NMR techniques in combination with constrained molecular dynamics (MD) simulations revealed that two of these analogues, 8a and 10a, have folded conformations composed of an unusual nine-membered pseudo

  合成了呋喃糖糖氨基酸（1），用作二肽等位基因，以诱导小的线性肽中有趣的转弯结构。它们属于新设计的杂合结构的新种类，其在刚性呋喃糖糖环上同时带有氨基和羧基。四个这样的分子，6-氨基-2,5-脱水-6-脱氧-D-葡萄糖酸（3，Gaa）及其甘露糖醛酸（4，Maa），偶氮（5，Iaa）和3,4-二氧杂豆酸合成了（6，ddIaa）同源物。合成遵循新的反应路径，其中在γ-吡啶鎓重铬酸吡啶鎓羟基氧化过程中，发生了γ-苄氧基氧与己糖衍生的末端氮丙啶环在2中的分子内5-exo S（N）2开环基团具有羧基功能，导致一步形成呋喃糖糖氨基酸骨架。将这些呋喃类糖氨基酸掺入亮氨酸脑啡肽中代替其Gly-Gly部分，得到类似物8-11。通过圆二色性（CD）和各种NMR技术，结合受限的分子动力学（MD）模拟，对这些分子进行了详细的结构分析，结果表明，这些类似物中的两个8a和10a具有折叠结构，由不寻常的九元伪β-在LeuN
• Synthesis, Conformational Analysis, and Complexation Study of an Iminosugar-Aza-Crown, a Sweet Chiral Cyclam Analog
  作者：Alexandra Bordes、Ana Poveda、Thibault Troadec、Antonio Franconetti、Ana Ardá、Flavie Perrin、Mickaël Ménand、Matthieu Sollogoub、Jerôme Guillard、Jérôme Désiré、Raphaël Tripier、Jesús Jiménez-Barbero、Yves Blériot

  DOI：10.1021/acs.orglett.0c00503

  日期：2020.3.20

  A new family of chiral C2 symmetric tetraazamacrocycles, coined ISAC for IminoSugar Aza-Crown, incorporating two iminosugars adopting a 4C1 conformation is disclosed. Multinuclear NMR experiments on the corresponding Cd2+ complex show that the ISAC is a strong chelator in water and its tetramine cavity adopts a conformation similar to that of the parent Cd–cyclam complex. Similar behavior is observed

  公开了一种新的手性C 2对称四氮杂大环族，其为IminoSugar Aza-Crown的ISAC，结合了两个采用4 C 1构象的亚氨基糖。在相应的Cd 2+络合物上进行的多核NMR实验表明，ISAC在水中是很强的螯合剂，其四胺腔具有与母体Cd–cyclam络合物相似的构象。在溶液中使用Cu 2+可以观察到类似的行为，与Cu–cyclam配合物相比，稳定性更高。
• Synthesis of methyl 2,3-O-glycopyranosylidene-α-d-mannopyranosides having various substituents
  作者：Juji Yoshimura、Katsuji Asano、Kazuyuki Umemura、Shigeomi Horito、Hironobu Hashimoto

  DOI：10.1016/0008-6215(83)84016-6

  日期：1983.9

  title compounds were obtained by condensation of d -glucono-, d -galactono-, or l - glycero - d - gluco -heptono-1,5-lactones with methyl 2,3-di- O -(trimethylsilyl)-α- d -mannopyranosides having various substituents on C-4 and C-6, in the presence of trimethylsilyl trifluoromethanesulfonate as the catalyst. Except for a 6-acetoxyl group on a lactone component and a ( tert -butyldiphenylsiloxy) group

  摘要标题化合物是通过将d-葡萄糖酸-，d-半乳糖基-或l-甘油-d-葡萄糖-庚基-1,5-内酯与2,3-二甲基O-（三甲基甲硅烷基）-α缩合而获得的。在三甲基甲硅烷基三氟甲磺酸盐作为催化剂的存在下，在C-4和C-6上具有各种取代基的-d-甘露吡喃糖苷。除了内酯组分上的6-乙酰氧基和（叔丁基二苯基甲硅烷氧基）基团外，常用的C-取代基，例如苄氧基，烯丙氧基，叠氮基，酰氧基，（甲硫基）甲氧基和甲氧基，均不能阻止这种情况的发生。缩合。
• Selective trihydroxyazepane NagZ inhibitors increase sensitivity of Pseudomonas aeruginosa to β-lactams
  作者：Martine Mondon、Soo Hur、Grishma Vadlamani、Prerana Rodrigues、Polina Tsybina、Antonio Oliver、Brian L. Mark、David J. Vocadlo、Yves Blériot

  DOI：10.1039/c3cc46646a

  日期：——

  AmpC beta-lactamase confers resistance to beta-lactam antibiotics in many Gram negative bacteria. Inducible expression of AmpC requires an N-acetylglucosaminidase termed NagZ. Here we describe the synthesis and characterization of hydroxyazepane inhibitors of NagZ. We find that these inhibitors enhance the susceptibility of clinically relevant Pseudomonas aeruginosa to beta-lactams.

  AmpCβ-内酰胺酶赋予许多革兰氏阴性细菌对β-内酰胺抗生素的抗性。AmpC的诱导表达需要一个称为NagZ的N-乙酰氨基葡糖苷酶。在这里，我们描述了NagZ的羟基氮杂环庚烷抑制剂的合成和表征。我们发现这些抑制剂增强了临床相关的铜绿假单胞菌对β-内酰胺的敏感性。
• Skeletal rearrangement of seven-membered iminosugars: Synthesis of (−)-adenophorine, (−)-1-epi-adenophorine and derivatives and evaluation as glycosidase inhibitors
  作者：Martine Mondon、Frédéric Lecornué、Jérôme Guillard、Shinpei Nakagawa、Atsushi Kato、Yves Blériot

  DOI：10.1016/j.bmc.2013.03.035

  日期：2013.8

  investigated for the alkylation step including organomagnesium, organolithium, organozinc, organoaluminum and organocerium reagents. While diallylzinc proved to be the most efficient to introduce an allyl substituent, disappointing results were obtained with the other organometallic species leading either to lower yields or no reaction. Enzymatic assays indicate that (−)-adenophorine is a moderate α-l-fucosidase

  合成了天然产物（+）-腺苷及其1-表-，1-同-类似物和其他衍生物的镜像，并将其评估为糖苷酶抑制剂。合成策略是基于四羟基化的C-烷基氮杂环庚烷的骨架重排，所述四羟基化的C-烷基氮杂环庚烷通过Staudinger / azaWittig /烷基化序列从糖衍生​​的叠氮吲哚开始获得。已经针对烷基化步骤研究了几种有机金属物质，包括有机镁，有机锂，有机锌，有机铝和有机铈试剂。事实证明，二烯丙基锌是引入烯丙基取代基最有效的方法，但使用其他有机金属物种却获得了令人失望的结果，导致收率降低或没有反应。酶促测定表明（-）-腺苷是中等α-1-岩藻糖苷酶抑制剂。