phenyl 2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-1-thio-β-D-glucopyranoside | 188583-24-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl 2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-1-thio-β-D-glucopyranoside
• 英文别名: thiophenyl 2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranoside；phenyl 2-deoxy-1-thio-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranoside；2,2,2-Trichloroethyl ((2S,3R,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-(phenylthio)tetrahydro-2H-pyran-3-yl)carbamate；2,2,2-trichloroethyl N-[(2S,3R,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-phenylsulfanyloxan-3-yl]carbamate
• CAS: 188583-24-6
• 化学式: C₁₅H₁₈Cl₃NO₆S
• 分子量: 446.736
• InChiKey: LCQAHPRLLBMKDG-VEGXAWMVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  134
• 氢给体数：
  4
• 氢受体数：
  7

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  ——	2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-D-glucopyranose	172490-46-9	C9H14Cl3NO7	354.572

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  ——	phenyl O-(β-D-galactopyranosyl)-(1-4)-2-deoxy-1-thio-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranoside	512174-10-6	C21H28Cl3NO11S	608.878
  ——	phenyl 2-deoxy-1-thio-3-O-(2,2,2-trichloroethoxycarbonyl)-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranoside	188583-27-9	C18H19Cl6NO8S	622.135
  ——	phenyl 4,6-benzylidene-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-1-thio-α-D-glucopyranoside	371123-28-3	C22H22Cl3NO6S	534.845
  ——	phenyl 2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-3,4,6-tri-O-trimethylsilyl-1-thio-β-D-glucopyranoside	1529807-60-0	C24H42Cl3NO6SSi3	663.282
  ——	phenyl 6-O-benzyloxymethyl-2-deoxy-1-thio-3-O-(2,2,2-trichloroethoxycarbonyl)-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranoside	188583-28-0	C26H27Cl6NO9S	742.286
  ——	phenyl 2-deoxy-3,4-O-(2,3-dimethoxybutane-2,3-diyl)-1-thio-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranoside	1283073-38-0	C21H28Cl3NO8S	560.88
  ——	phenyl 2-[(2,2,2-trichloroethoxy)carbonyl]amino-4,6-O-p-methoxybenzylidene-2-deoxy-1-thio-β-D-glucopyranoside	188583-25-7	C23H24Cl3NO7S	564.871
  ——	phenyl O-(5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonate)-(2-3)-O-(β-D-galactopyranosyl)-(1-4)-2-deoxy-1-thio-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranoside	744193-99-5	C32H45Cl3N2O19S	900.136
  ——	phenyl 2-deoxy-4,6-O-p-methoxybenzylidene-1-thio-3-O-(2,2,2-trichloroethoxycarbonyl)-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranoside	188583-26-8	C26H25Cl6NO9S	740.27
  ——	phenyl 2-deoxy-3,4-O-(2,3-dimethoxybutane-2,3-diyl)-1-thio-6-O-p-toluenesulfonyl-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranoside	1283073-40-4	C28H34Cl3NO10S2	715.07

反应信息

• 作为反应物：
  描述：

  phenyl 2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-1-thio-β-D-glucopyranoside 在 UDP-galactose 4-epimerase 、 β(1-4)galactosyltransferase 、 sialyltransferase FUS-01/2 、 magnesium chloride 、 manganese(ll) chloride 作用下， 以 various solvent(s) 为溶剂， 反应 22.0h， 生成 phenyl O-(5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonate)-(2-3)-O-(β-D-galactopyranosyl)-(1-4)-2-deoxy-1-thio-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranoside
  参考文献：
  名称：

  Simplifying Oligosaccharide Synthesis:  Efficient Synthesis of Lactosamine and Siaylated Lactosamine Oligosaccharide Donors

  摘要：

  A practical sequence is described for converting D-glucosamine into peracetylated Gal(beta-1,4)-GlcNTroc(beta1-S)Ph and Neu5Ac(alpha-2,3)Gal(beta-1,4)GlcNTroc(beta1-S)Ph building blocks using a synthetic strategy based on chemoenzymatic oligosaccharide synthesis. The known trichloroethoxycarbonyl, N-Troc, protecting group was selected as a suitable protecting group for both enzymatic and chemical reaction conditions. These oligosaccharide building blocks proved effective donors for the,beta-selective glycosylation of the unreactive OH-3 of a polymeric PEG-bound acceptor and for the axial OH-2 of a mannose acceptor in good yields. The resulting complex oligosaccharides are useful for vaccine and pharmaceutical applications.

  DOI：

  10.1021/jo026569v
• 作为产物：
  描述：

  2-氨基-2-脱氧葡萄糖盐酸盐 在 吡啶 、 4-二甲氨基吡啶 、 三氟化硼乙醚 、 sodium methylate 、 碳酸氢钠 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 47.0h， 生成 phenyl 2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  Lewis X-O -Core-1苏氨酸的合成：O-连接的Lewis X糖肽的结构单元

  摘要：

  LewisX（LeX）是一种分支的三糖Galβ1→4（Fucα1→3）GlcNAc，在许多细胞表面糖蛋白上表达，在先天性和适应性免疫应答中起关键作用。然而，携带LeX的糖肽的有效合成仍然是LeX决定簇结构功能研究的主要限制。在这里我们报告了使用区域选择性的1-苯亚磺酰基哌啶/三氟甲磺酸酐促进的[3 + 2]糖基化的LeX五糖1的总合成。Fmoc-苏氨酸氨基酸的存在促进了五糖在固相肽合成中的掺入，提供了通往多种O-连接的LeX糖肽的途径。所描述的方法广泛适用于合成多种复杂的糖肽，这些糖肽包含O-连接的LeX或唾液酸化的LewisX（sLeX）。

  DOI：

  10.1016/j.carres.2017.10.002

文献信息

• Design and Synthesis of a Novel Ganglioside Ligand for Influenza A Viruses †
  作者：Tomohiro Nohara、Akihiro Imamura、Maho Yamaguchi、Kazuya I. P. J. Hidari、Takashi Suzuki、Tatsuya Komori、Hiromune Ando、Hideharu Ishida、Makoto Kiso

  DOI：10.3390/molecules17089590

  日期：——

  A novel ganglioside bearing Neua2-3Gal and Neua2-6Gal structures as distal sequences was designed as a ligand for influenza A viruses. The efficient synthesis of the designed ganglioside was accomplished by employing the cassette coupling approach as a key reaction, which was executed between the non-reducing end of the oligosaccharide and the cyclic glucosylceramide moiety. Examination of its binding activity to influenza A viruses revealed that the new ligand is recognized by Neua2-3 and 2-6 type viruses.

  设计了一种新型神经节苷脂，其远端序列包含NeuA2-3Gal和NeuA2-6Gal结构，作为流感A病毒的配体。通过采用盒式偶联法作为关键反应，实现了该设计神经节苷脂的高效合成，该反应在低聚糖的非还原端与环状葡萄糖基神经酰胺之间进行。检测其与流感A病毒的结合活性发现，新型配体被NeuA2-3型和2-6型病毒所识别。
• A 3,4-<i>trans</i>-Fused Cyclic Protecting Group Facilitates α-Selective Catalytic Synthesis of 2-Deoxyglycosides
  作者：Edward I. Balmond、David Benito-Alifonso、Diane M. Coe、Roger W. Alder、Eoghan M. McGarrigle、M. Carmen Galan

  DOI：10.1002/anie.201403543

  日期：2014.7.28

  disaccharides or glycoconjugates with high α‐selectivity and yields (77–97 %) using a trans‐fused cyclic 3,4‐O‐disiloxane protecting group and TsOH⋅H2O (1 mol %) as a catalyst. Control of the anomeric selectivity arises from conformational locking of the intermediate oxacarbenium cation. Glucals outperform rhamnals because the C6 side‐chain conformation augments the selectivity.

  已经开发出一种实用的方法，使用反式稠合环状 3,4-O-二硅氧烷保护基团和 TsOH⋅H 2 O ，将葡糖和鼠李糖转化为具有高α-选择性和产率（77-97%）的二糖或糖缀合物（ 1 mol%) 作为催化剂。异头选择性的控制来自中间氧杂碳鎓阳离子的构象锁定。Glucals 优于鼠李糖醇，因为 C6 侧链构象增强了选择性。
• Protecting Group-Free Glycoligation by the Desulfurative Rearrangement of Allylic Disulfides as a Means of Assembly of Oligosaccharide Mimetics
  作者：Venkataraman Subramanian、Myriame Moumé-Pymbock、Tianshun Hu、David Crich

  DOI：10.1021/jo102411j

  日期：2011.5.20

  2-(2-Pyridyldithio-3-butenyl) glycosides react with carbohydrate-based thiols in a two-step process involving sulfenyl transfer followed by desulfurative 2,3-allylic rearrangement, promoted by either triphenylphosphine or silver nitrate, to give novel saccharide mimetics. In an alternative embodiment of the same chemistry anomeric thiols are coupled with carbohydrates derivatized in the form of 2-

  2-(2-Pyridyldithio-3-butenyl) 糖苷与基于碳水化合物的硫醇在两步过程中反应，包括硫基转移，然后脱硫 2,3-烯丙基重排，由三苯基膦或硝酸银促进，得到新型糖类模拟物. 在相同化学异头硫醇的替代实施方案中，与以2-(2-吡啶基二硫代-3-丁烯基)醚形式衍生的碳水化合物偶联。这种新的糖基化方法不需要保护羟基，并且与乙酰胺、叠氮化物、三氯乙氧基氨基甲酸酯和硫糖苷的存在兼容。通用主题的变化使得能够制备还原性和非还原性寡糖以及非糖苷连接系统的模拟物。
• Synthesis and protein binding studies of a peptide fragment of clathrin assembly protein AP180 bearing an O-linked β-N-acetylglucosaminyl-6-phosphate modification
  作者：Mark E. Graham、Robin S. Stone、Phillip J. Robinson、Richard J. Payne

  DOI：10.1039/c2ob07139h

  日期：——

  A novel post-translational modification of threonine, β-N-acetylglucosaminyl-phosphate, was recently discovered on assembly protein AP180, a protein which plays a crucial role in clathrin coated vesicle formation in synaptic vesicle endocytosis (SVE). Herein, we report studies aimed at probing the effect of this modification on binding to proteins in rat brain lysate using pull down experiments with peptide fragments of AP180.

  最近发现了一种新型的丝氨酸翻译后修饰——β-N-乙酰氨基葡萄糖苷酸磷酸，它出现在组装蛋白AP180上。AP180在突触小泡内吞过程中对网格蛋白涂层囊泡的形成起着至关重要的作用。在本文中，我们报告了旨在探究这种修饰对与大鼠脑裂解液中蛋白质结合影响的研究，采用了AP180的肽片段进行拉分实验。
• Lipid A and Related Compounds. XXXII. Synthesis of Biologically Active N-Acylated L-Homoserine-Containing D-Glucosamine-4-phosphate Derivatives Structurally Related to Lipid A.
  作者：Keisuke MIYAJIMA、Kazuo ACHIWA

  DOI：10.1248/cpb.45.312

  日期：——

  New N-acylated L-homoserine-containing non-phosphorylated and phosphorylated D-glucosamine derivatives were synthesized as mimicks of lipid A disaccharide. Some of the synthesized compounds exhibited mitogenic activity and nitric oxide (NO) productivity.

  合成了新的N-酰化L-同脯氨酸非磷酸化和磷酸化的D-葡萄糖胺衍生物，作为脂质A二糖的模拟物。其中一些合成的化合物表现出促增殖活性和一氧化氮（NO）产生能力。