N-fluoren-9-ylmethoxycarbonyl-S-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-L-cysteine | 139254-40-3

• 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: N-fluoren-9-ylmethoxycarbonyl-S-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-L-cysteine
• 英文别名: N^α-(9-fluorenylmethoxycarbonyl)-3-S-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-L-cysteine；N^α-fluoren-9-ylmethoxycarbonyl-S-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-L-cysteine；N-fluorenylmethoxycarbonyl-S-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-L-cysteine；(2R)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-[(2S,3R,4S,5S,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]sulfanylpropanoic acid
• CAS: 139254-40-3
• 化学式: C₃₂H₃₅NO₁₃S
• 分子量: 673.695
• InChiKey: SVXANUGGFUROLG-BPUYOJAOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  47
• 可旋转键数：
  17
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  215
• 氢给体数：
  2
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  三氟乙酸五氟苯酯 、 N-fluoren-9-ylmethoxycarbonyl-S-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-L-cysteine 在 吡啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以67%的产率得到N-fluoren-9-ylmethoxycarbonyl-S-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-L-cysteine pentafluorophenyl ester
  参考文献：
  名称：

  Preparation of S‐ and N‐Linked Glycosylated Amino Acid Building Blocks for Solid‐phase Glycopeptide Library Synthesis*

  摘要：

  A general route for the preparation of 1,2-trans-linked S-glycosylated amino acid building blocks by a Lewis-acid-promoted condensation of peracetylated glycosyl donors and N-alpha-Fmoc-Cys-OH, in good overall yield, is described. In addition, a short and time-efficient route was applied for the synthesis of N-glycosylated amino acid building blocks in good overall yields by coupling unprotected glycosylamines and N-alpha-Fmoc-Asp(OH)-(OBu)-Bu-t using TBTU activation.

  DOI：

  10.1081/car-200066915
• 作为产物：
  描述：

  Fmoc-Cys[Trt]-OAllyl 在 四(三苯基膦)钯 、 2-[[三(羟甲基)甲基]氨基]乙磺酸 、 aniline p-toluenesulfinate 、 四氯化锡 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 8.0h， 生成 N-fluoren-9-ylmethoxycarbonyl-S-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-L-cysteine
  参考文献：
  名称：

  Solid-phase carbohydrate synthesis via on-bead protecting group chemistry

  摘要：

  Di- and tri-saccharides were synthesized on a solid phase. The procedure started with a non-protected sugar linked via either cysteine or glutamine to a polystyrene resin. Selective dimethoxytritylation chemistry and subsequent steps yielded a resin-bound acceptor that could be glycosylated to yield beta 1,6-linked disaccharides. Reiteration of the procedure produced the trisaccharide. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.03.051

文献信息

• Preparation of S-glycoside surfactants and cysteine thioglycosides using minimally competent Lewis acid catalysis
  作者：Lajos Z. Szabó、Dillon J. Hanrahan、Evan M. Jones、Erin Martin、Jeanne E. Pemberton、Robin Polt

  DOI：10.1016/j.carres.2015.12.008

  日期：2016.3

  Here we report a method for the preparation of anomerically pure beta-S-glycopyranosides (1,2-trans-glycosides) from the corresponding peracetate donors. S-glycosylation was performed in CHCl3 at reflux in the presence of a catalytic amount of InBr3. Deacylation of the intermediate peracetates were achieved under Zemplen conditions. Five pyranose examples, monosaccharides D-glucose and D-galactose

  在这里，我们报告了一种从相应的过乙酸盐供体制备异头纯β-S-吡喃糖苷（1,2-反式糖苷）的方法。在催化量的 InBr3 存在下，在 CHCl3 中回流进行 S-糖基化。在 Zemplen 条件下实现中间体过乙酸酯的脱酰化。五个吡喃糖的例子，单糖 D-葡萄糖和 D-半乳糖和二糖纤维二糖、麦芽糖和乳糖，被用作供体，五种硫醇，包括 α/ω 二硫醇和 Fmoc-L-半胱氨酸被用作受体。报告了先前未描述的化合物的熔点、高分辨率 MS、αD 和 NMR 数据((1)H 和 (13)C，包括 COSY、HSQC 和 HMBC)。
• Preparation of building blocks for glycopeptide synthesis by glycosylation of Fmoc amino acids having unprotected carboxyl groups
  作者：Lourdes A. Salvador、Mikael Elofsson、Jan Kihlberg

  DOI：10.1016/0040-4020(95)00224-v

  日期：1995.5

  Nα-Fmoc amino acids with an unprotected α-carboxyl group have been glycosylated with carbohydrate 1,2-trans peracetates using Lewis acids as promoters. Aliphatic and phenolic O- and S-glycosides of amino acids, with a 1,2-trans anomeric configuration, were obtained as products in 34–65% yields. The glycosylated building blocks have the protective groups of choice (i.e. O-acetyl and Nα-Fmoc) for direct

  Ñ α -Fmoc氨基酸与未保护的α-羧基已被糖基化的碳水化合物与1,2-反式使用路易斯酸作为促进剂过乙。获得具有1，2-反式异头构型的氨基酸的脂肪族和酚类O-和S-糖苷，收率为34–65％。糖基化的构建块有选择的保护基团（即ø -乙酰基和Ñ α -Fmoc）在糖肽的逐步合成直接使用。起始原料容易获得，并且该方法不需要合成碳水化合物化学方面的丰富经验。
• Building blocks for glycopeptide synthesis: glycosylation of 3-mercaptopropionic acid and Fmoc amino acids with unprotected carboxyl groups
  作者：Mikael Elofsson、Björn Walse、Jan Kihlberg

  DOI：10.1016/0040-4039(91)80548-k

  日期：1991.12

  3-Mercaptopropionic acid and Fmoc amino acids, having unprotected carboxyl groups, were glycosylated with sugar 1,2-trans-acetates in 90 and 53–65% yields, respectively, under Lewis acid promotion. The synthesis of a neoglycopeptide illustrates the use of the building blocks in solid phase peptide synthesis.

  在路易斯酸的促进下，将具有未保护羧基的3-巯基丙酸和Fmoc氨基酸分别与糖1,2-反式乙酸酯进行糖基化处理，产率分别为90％和53-65％。新糖肽的合成说明了结构单元在固相肽合成中的用途。
• Synthesis of the Bacteriocin Glycopeptide Sublancin 168 and <i>S</i>-Glycosylated Variants
  作者：Yves S. Y. Hsieh、Brendan L. Wilkinson、Mitchell R. O’Connell、Joel P. Mackay、Jacqueline M. Matthews、Richard J. Payne

  DOI：10.1021/ol300557g

  日期：2012.4.6

  The synthesis of sublancin 168, a unique S-glucosylated bacteriocin antibiotic, is described. The natural product and two S-glycosylated variants were successfully prepared via native chemical ligation followed by folding. The synthetic glycopeptides were shown to possess primarily an α-helical secondary structure by CD and NMR studies.

  描述了一种独特的S-葡萄糖基化细菌素抗生素sublancin 168的合成。通过天然化学连接然后折叠成功制备了天然产物和两个S-糖基化的变体。通过CD和NMR研究显示合成的糖肽主要具有α-螺旋二级结构。
• A General Strategy toward S-Linked Glycopeptides
  作者：Desiree A. Thayer、Henry N. Yu、M. Carmen Galan、Chi-Huey Wong

  DOI：10.1002/anie.200500090

  日期：2005.7.18