ethyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-galactofuranoside | 284030-01-9

• 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: ethyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-galactofuranoside
• 英文别名: ethyl 2,3,5,6-tetra-O-acetyl-1-thio-β-D-galactofuranoside；[(2R)-2-acetyloxy-2-[(2S,3S,4R,5S)-3,4-diacetyloxy-5-ethylsulfanyloxolan-2-yl]ethyl] acetate
• CAS: 284030-01-9
• 化学式: C₁₆H₂₄O₉S
• 分子量: 392.427
• InChiKey: TVDMMCURWUEDSS-CWVYHPPDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  26
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  140
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  ethyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-galactofuranoside 在 4 A molecular sieve 、 copper(II) bis(trifluoromethanesulfonate) 、 甲基三辛基氯化铵 、 copper(II) oxide 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 生成 6-O-(2,3,5,6-tetra-O-acetyl-β-D-galactofuranosyl)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose
  参考文献：
  名称：

  异头磺酰亚胺的合成及其作为新的糖基供体家族的用途

  摘要：

  我们介绍了一种方便的异头磺酰亚胺合成方法，其作为糖基供体的能力已经用各种亲硫试剂和受体进行了测试。

  DOI：

  10.1002/1099-0690(20021)2002:1<171::aid-ejoc171>3.0.co;2-7
• 作为产物：
  描述：

  1,2,3,5,6-penta-O-acetyl-D-galactofuranose 、 乙硫醇 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以55%的产率得到ethyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-galactofuranoside
  参考文献：
  名称：

  A General and Diastereoselective Synthesis of 1,2-cis-Hexofuranosides from 1,2-trans-Thiofuranosyl Donors

  摘要：

  DOI：

  10.1002/(sici)1099-0690(200004)2000:8<1423::aid-ejoc1423>3.0.co;2-9

文献信息

• Glycosylation and Pyranose-Furanose Isomerization of Carbohydrates Using HClO₄-SiO₂: Synthesis of Oligosaccharides Containing Galactofuranose
  作者：Anup Misra、Chinmoy Mukherjee

  DOI：10.1055/s-2007-965913

  日期：2007.3

  A series of di- and trisaccharides containing 6-O-linked galactofuranose were synthesized as an anomeric mixture of methyl glycosides using silica-supported perchloric acid.

  一系列含有6-O-连接的呋喃半乳糖的二糖和三糖被合成，它们是以甲基糖苷的异头混合物形式，通过硅胶负载的高氯酸作为催化剂。
• Synthesis of galactofuranose-based acceptor substrates for the study of the carbohydrate polymerase GlfT2
  作者：Rebecca A. Splain、Laura L. Kiessling

  DOI：10.1016/j.bmc.2010.04.068

  日期：2010.6.1

  Despite the prevalence and importance of carbohydrate polymers, the molecular details of their biosynthesis remain elusive. Many enzymes responsible for the synthesis of carbohydrate polymers require a 'primer' or 'initiator' carbohydrate sequence. One example of such an enzyme is the mycobacterial galactofuranosyltransferase GlfT2 (Rv3808c), which generates an essential cell wall building block. We recently demonstrated that recombinant GlfT2 is capable of producing a polymer composed of alternating beta-(1,5) and beta-(1,6)-linked galactofuranose (Galf) residues. Intriguingly, the length of the polymers produced from a synthetic glycosyl acceptor is consistent with those found in the cell wall. To probe the mechanism by which polymer length is controlled, a collection of initiator substrates has been assembled. The central feature of the synthetic route is a ruthenium-catalyzed cross-metathesis as the penultimate transformation. Access to synthetic substrates has led us to postulate a new mechanism for length control in this template-independent polymerization. Moreover, our investigations indicate that lipids possessing but a single galactofuranose residue can act as substrates for GlfT2. (C) 2010 Elsevier Ltd. All rights reserved.