3,4,6-Tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranosyl bromide | 67124-60-1

• 分子结构分类: 有机化合物
• 英文名称: 3,4,6-Tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranosyl bromide
• 英文别名: 3,4,6-tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-bromo-D-glucopyranose；3,4,6-tri-O-acetyl-2-deoxy-2-[(2,2,2-trichloroethoxy)carbonylamino]-alpha-d-glucopyranosyl bromide；[(2R,3S,4R,5R,6R)-3,4-diacetyloxy-6-bromo-5-(2,2,2-trichloroethoxycarbonylamino)oxan-2-yl]methyl acetate
• CAS: 67124-60-1
• 化学式: C₁₅H₁₉BrCl₃NO₉
• 分子量: 543.58
• InChiKey: IGLJUTJCXNPQND-VEGXAWMVSA-N

物化性质

• 熔点：
  97-98 °C(Solv: ethyl ether (60-29-7); hexane (110-54-3))
• 沸点：
  551.1±50.0 °C(Predicted)
• 密度：
  1.62±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  29
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  127
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  3,4,6-Tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranosyl bromide 在 palladium on activated charcoal 4 A molecular sieve 、 氢气 、 silver trifluoromethanesulfonate 、 锌 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 24.5h， 生成 N-(9-fluorenylmethoxycarbonyl)-(2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-β-D-glucopyranosyl)-L-serine
  参考文献：
  名称：

  Solid-Phase Synthesis of O-Linked Glycopeptide Analogues of Enkephalin

  摘要：

  The synthesis of 18 N-alpha -FMOC-amino acid glycosides for solid-phase glycopeptide assembly is reported. The glycosides were synthesized either from the corresponding O'Donnell Schiff bases or from N-alpha -FMOC-amino protected serine or threonine and the appropriate glycosyl bromide using Hanessian's modification of the Koenigs-Knorr reaction. Reaction rates of D-glycosyl bromides (e.g., acetobromoglucose) with the L- and D-forms of serine and threonine are distinctly different and can be rationalized in terms of the steric interactions within the two types of diastereomeric transition states for the D/L and D/D reactant pairs. The N-alpha -FMOC-protected glycosides [monosaccharides Xyl, Glc, Gal, Man, GlcNAc, and GalNAc; disaccharides Gal-beta (1-4)-Gle (lactose), Glc-beta-(1-4)-Glc (cellobiose), and Gal-alpha (1-6)-Glc (melibiose)] were incorporated into 22 enkephalin glycopeptide analogues. These peptide opiates bearing the pharmacophore H-Tyr-c[DCys-Gly-PheDCys]- were designed to probe the significance of the glycoside moiety and the carbohydrate-peptide linkage region in blood-brain barrier (BBB) transport, opiate receptor binding, and analgesia.

  DOI：

  10.1021/jo005712m
• 作为产物：
  描述：

  isopropyl 3,4,6-tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranoside 在 三甲基溴硅烷 、 zinc dibromide 作用下， 以 二氯甲烷 为溶剂， 反应 15.0h， 以88%的产率得到3,4,6-Tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranosyl bromide
  参考文献：
  名称：

  Direct Transformation of O-Glycoside into Glycosyl Bromide with the Combination of Trimethylsilyl Bromide and Zinc Bromide.

  摘要：

  已经开发出一种新颖的O-糖苷直接转化为溴代糖苷的方法，即使用三甲基溴化硅和溴化锌。在二氯甲烷中用三甲基溴化硅和溴化锌处理各种糖苷（3a-5a、10、12和14），分别得到溴代糖苷（6、11、13和15），产率分别为53%、85%、94%、47%、41%和40%。

  DOI：

  10.1248/cpb.39.2502

文献信息

• Synthesis of Peptidoglycan Units with UDP at the Anomeric Position
  作者：Thierry Lioux、Roger Busson、Jef Rozenski、Martine Nguyen-Distèche、Jean-Marie Frère、Piet Herdewijn

  DOI：10.1135/cccc20051615

  日期：——

  A series of UDP-disaccharide peptide compounds were synthesized as synthetic substrate analogues or potential inhibitors of glycosyl transferase. Fluorescent compounds have been prepared with the aim of developing a screening method for selecting transglycosylase inhibitors.

  一系列UDP-二糖肽化合物被合成为糖基转移酶的合成底物类似物或潜在抑制剂。已经制备了荧光化合物，目的是开发一种筛选方法，用于选择转糖基酶抑制剂。
• General methods for .alpha.- or .beta.-O-Ser/Thr glycosides and glycopeptides. Solid-phase synthesis of O-glycosyl cyclic enkephalin analogs
  作者：Robin Polt、Lajos Szabo、Jennifer Treiberg、Yushun Li、Victor J. Hruby

  DOI：10.1021/ja00052a022

  日期：1992.12

  O-Linked glycopeptides have been efficiently synthesis using the highly nucleophilic α-imino esters (O'Donnell's Schiff bases) derived from L-serine (3a-c), L-threonine (4a,b), and a dipeptide ester (5). General methodology has been developed which can provide β-glycosides of β-hydroxy-α-amino acid derivatives 6-16 in excellent yield (63-94%) and excellent selectivity (>20:1) using Hanessian's modification

  使用衍生自 L-丝氨酸 (3a-c)、L-苏氨酸 (4a,b) 和二肽酯 (5) 的高度亲核性 α-亚氨基酯（O'Donnell's Schiff 碱）已有效合成 O-连接糖肽. 已开发出通用方法，可以使用 Hanessian 修饰或 Helferich 修饰以优异的产率 (63-94%) 和优异的选择性 (>20:1) 提供 β-羟基-α-氨基酸衍生物 6-16 的 β-糖苷。 Koenigs-Knorr 反应。同样，使用 Lemieux 的原位异构化方法实现了选择性 α-糖基化。丝氨酸/苏氨酸羟基的亲核性增加已被证明是由于分子内氢键连接到 N=CPh 2 部分。中间席夫碱的脱保护已被证明，
• Chemical synthesis of 1-dephospho derivative of lipid A
  作者：S. Kusumoto、H. Yoshimura、M. Imoto、T. Shimamoto、T. Shiba

  DOI：10.1016/s0040-4039(00)61962-7

  日期：1985.1

  1-Dephospho E. coli lipid A () was synthesized and shown to be identical with the corresponding derivative isolated from bacterial cells. This provides the unequivocal evidence supporting the structure of E. coli lipid A () recently proposed by us.

  合成了1-Dephospho大肠杆菌脂质A（），显示与从细菌细胞中分离出的相应衍生物相同。这提供了明确的证据来支持我们最近提出的大肠杆菌脂质A（）的结构。
• Synthesis and antituberculosis activity of the first macrocyclic glycoterpenoids comprising glucosamine and diterpenoid isosteviol
  作者：Bulat F. Garifullin、Irina Yu. Strobykina、Radmila R. Sharipova、Marionella A. Kravchenko、Olga V. Andreeva、Olga B. Bazanova、Vladimir E. Kataev

  DOI：10.1016/j.carres.2016.05.007

  日期：2016.8

  The first macrocyclic glycoterpenoids comprising glucosamine and diterpenoid isosteviol moieties were synthesized and evaluated for inhibition activity against Mycobacterium tuberculosis H37Rv.

  合成了包含葡糖胺和二萜类异戊烯醇部分的第一大环糖类萜，并评估了其对结核分枝杆菌H37Rv的抑制活性。
• Synthesis and cytotoxicity of the conjugates of diterpenoid isosteviol and <i>N</i>-acetyl-D-glucosamine
  作者：Bulat F. Garifullin、Irina Yu. Strobykina、Leysan R. Khabibulina、Anastasiya S. Sapunova、Aleksandra D. Voloshina、Radmila R. Sharipova、Bulat I. Khairutdinov、Yuriy F. Zuev、Vladimir E. Kataev

  DOI：10.1080/14786419.2019.1650355

  日期：2021.4.18

  Abstract A series of conjugates of diterpenoid isosteviol (16-oxo-ent-beyeran-19-oic acid) and N-acetyl-D-glucosamine was synthesised and their cytotoxicity against several human cancer cell lines (M-Hela, MCF-7, Hep G2, Panc-1, PC-3), as well as normal human cell lines (WI-38, Chang liver) was assayed. Most of the conjugates were found to be cytotoxic against the mentioned cancer cell lines in the

  摘要 一系列二萜异甜菊醇的偶联物（16氧代ENT -beyeran -19-酸）和ñ -乙酰基d -葡糖胺的合成和它们对几种人癌细胞系的细胞毒性（M-的Hela，MCF-7，喉癌测定了G2，Panc-1，PC-3）以及正常人细胞系（WI-38，常肝）。发现大多数缀合物在IC 50值为13–89 µM的范围内对上述癌细胞系具有细胞毒性。两种先导化合物14a和14b对M-Hela的选择性细胞毒性（IC 50 13和14 µM）是对照中抗癌药物他莫昔芬的细胞毒性的两倍（IC 5028 µM）。发现前导化合物对M-Hela细胞的细胞毒性活性归因于细胞凋亡的诱导。