Acetic acid (3R,4R,5S,6R)-2,5-diacetoxy-6-acetoxymethyl-3-(9H-fluoren-9-ylmethoxycarbonylamino)-tetrahydro-pyran-4-yl ester | 1040868-13-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: Acetic acid (3R,4R,5S,6R)-2,5-diacetoxy-6-acetoxymethyl-3-(9H-fluoren-9-ylmethoxycarbonylamino)-tetrahydro-pyran-4-yl ester
• CAS: 1040868-13-0
• 化学式: C₂₉H₃₁NO₁₁
• 分子量: 569.565
• InChiKey: GZHWRAQZNRGWCI-OYDXEKDZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.61
• 重原子数：
  41.0
• 可旋转键数：
  8.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  152.76
• 氢给体数：
  1.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  Acetic acid (3R,4R,5S,6R)-2,5-diacetoxy-6-acetoxymethyl-3-(9H-fluoren-9-ylmethoxycarbonylamino)-tetrahydro-pyran-4-yl ester 在 溶剂黄146 、 肼 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.83h， 生成 2-deoxy-3,4,6-tri-O-acetyl-2-(9-fluorenylmethoxycarbonyl)-D-glucopyranose
  参考文献：
  名称：

  Convenient Synthesis of NCS−Chromophore Metabolite Isosteres:  Binding Agents for Bulged DNA Microenvironments

  摘要：

  A designed molecule with capacity to bind DNA bulges (20) has been prepared from readily available starting materials. The spirocyclic template was modeled on a metabolite of neocarzinostatin chromophore (NCSi-gb) and is equipped with functionality to enable convenient bioassay. Preliminary studies confirm binding at specific bulged sequences and induction of polymerase-mediated slippage events. The target compound offers a convenient means to study affinity for unique bulged motifs and for use as a molecular biology reagent.

  DOI：

  10.1021/ol0400591
• 作为产物：
  描述：

  氯甲酸-9-芴基甲酯 在 三乙胺 作用下， 以 吡啶 、 甲醇 、 二氯甲烷 为溶剂， 反应 20.0h， 生成 Acetic acid (3R,4R,5S,6R)-2,5-diacetoxy-6-acetoxymethyl-3-(9H-fluoren-9-ylmethoxycarbonylamino)-tetrahydro-pyran-4-yl ester
  参考文献：
  名称：

  O-烷基 S-(吡啶-2-基)碳硫醇盐：用于氨基烷氧基羰基化的操作简单且氮选择性高的试剂

  摘要：

  通过与 O-烷基 S-(吡啶-2-基)碳硫醇盐在适当的溶剂中在室温下在空气中反应，氨基以良好的产率被选择性地保护。甚至含有多个羟基的葡糖胺也在甲醇中被选择性地 N 保护。

  DOI：

  10.1055/s-0039-1690856

文献信息

• Selective N‐Deacetylation and Functionalization of Aminosugars
  作者：Sam J. Moons、Alexander D. Robertson、Thomas J. Boltje

  DOI：10.1002/ejoc.202200659

  日期：2022.8.19

  A mild and efficient one-pot protocol to selectively remove N-acetyl groups, and subsequently functionalize the generated amines, is reported. Common functional groups, such as esters, carbamates and thioglycosides, are tolerated.

  报道了一种温和有效的一锅法选择性去除N-乙酰基，随后对生成的胺进行功能化。可以耐受常见的官能团，例如酯、氨基甲酸酯和硫糖苷。
• Catalytic Cleavage of the 9-Fluorenylmethoxycarbonyl (Fmoc) Protecting Group under Neat Conditions
  作者：Serena Traboni、Fabiana Esposito、Marcello Ziaco、Noemi De Cesare、Emiliano Bedini、Alfonso Iadonisi

  DOI：10.1021/acs.orglett.4c00918

  日期：2024.4.19

  This work reports the first solvent-free catalytic approach for the cleavage of the fluorenylmethoxycarbonyl (Fmoc) protecting group from amine and alcohol functionalities. Various saccharide, peptide, and glyco-amino acid substrates were efficiently deprotected by simple treatment with 20 mol % neat 4-dimethylaminopyridine (DMAP) (one of the effective base catalysts found), without any solvent or

  这项工作报告了第一个无溶剂催化方法，用于从胺和醇官能团中裂解芴基甲氧基羰基 (Fmoc) 保护基团。通过用 20 mol% 纯 4-二甲基氨基吡啶 (DMAP)（已发现的有效碱催化剂之一）进行简单处理，即可有效脱除各种糖、肽和糖基氨基酸底物，无需任何溶剂或化学计量添加剂。最终通过一锅法、碱催化、无溶剂多步序列将 Fmoc 裂解与酯化、酰胺化和/或糖基化步骤相结合，组装出小型模型结构。
• On-Chip Synthesis and Label-Free Assays of Oligosaccharide Arrays
  作者：Lan Ban、Milan Mrksich

  DOI：10.1002/anie.200704998

  日期：2008.4.21
• Synthesis and human telomeric G-quadruplex DNA-binding activity of glucosaminosides of shikonin/alkannin
  作者：Hao He、Li-Ping Bai、Zhi-Hong Jiang

  DOI：10.1016/j.bmcl.2011.12.143

  日期：2012.2

  The N-acetyl glucosaminosides of shikonin/alkannin were synthesized by chemical glycosylation, which provided an ideal approach to resolve the mixture of enantiomeric shikonin and alkannin co-existed in the Chinese herbs. The glycosylated shikonin and alkannin exhibited stronger binding activity to human telomeric G-quadruplex DNA than their parent structures. This research indicated that glycosylation of natural product with amino sugars is an effective strategy to improve their DNA-binding affinity. (C) 2012 Elsevier Ltd. All rights reserved.