2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose | 5239-08-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose
• 英文别名: [(2R,3S,4S,5R,6R)-3,4,5-triacetyloxy-6-[[(1S,2R,6R,8R,9S)-4,4,11,11-tetramethyl-3,5,7,10,12-pentaoxatricyclo[7.3.0.02,6]dodecan-8-yl]methoxy]oxan-2-yl]methyl acetate
• CAS: 5239-08-7
• 化学式: C₂₆H₃₈O₁₅
• 分子量: 590.579
• InChiKey: KBXNZSMACDLJNP-RYMJVJABSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  41
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  170
• 氢给体数：
  0
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose 在 水 、 氢溴酸 、 乙酸酐 作用下， 以 溶剂黄146 为溶剂， 反应 50.5h， 生成 2,3,4-tri-O-acetyl-6-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-α-D-galactopyranosyl bromide
  参考文献：
  名称：

  Glaudemans, Cornelis P.J.; Lehmann, Jochen; Scheuring, Markus, Angewandte Chemie, 1989, vol. 101, # 12, p. 1730 - 1731

  摘要：

  DOI：
• 作为产物：
  描述：

  S-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl) methanethiosulfonate 在 N-碘代丁二酰亚胺 、 4 A molecular sieve 、 三乙基硅基三氟甲磺酸酯 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 26.0h， 生成 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose
  参考文献：
  名称：

  Glycosyl Disulfides:  Novel Glycosylating Reagents with Flexible Aglycon Alteration

  摘要：

  Glycosyl disulfides have been shown for the first time to be effective glycosyl donors. Glucosylation and galactosylation of a panel of representative alcohol acceptors allowed the formation of 28simple glycosides, disaccharides, and glycoamino acids in yields of up to 90%. As well as providing a novel class of effective glycosyl donors, the ability to easily alter the nature of the aglycon and the ability to differently activate donors that differ only in their aglycon simply through altering conditions lends glycosyl disulfide donors to their use in latent-active reactivity tuning Strategies,.

  DOI：

  10.1021/jo051374j

文献信息

• Amberlyst 15 as a mild and effective activator for the glycosylation with disarmed glycosyl trichloroacetimidate donors
  作者：Qiang Tian、Shuo Zhang、Qian Yu、Mei-Bo He、Jin-Song Yang

  DOI：10.1016/j.tet.2006.12.091

  日期：2007.3

  Amberlyst 15 acidic resin has been shown to be a mild and effective activator for the glycosylation with commonly used disarmed glycosyl trichloroacetimidate donors. Glucosylation, galactosylation, rhamnosylation, and lactosylation of a panel of representative alcohol and thiol acceptors promoted by Amberlyst 15 allowed for the formation of structurally diverse O- or S-linked oligosaccharides and glycosylated

  Amberlyst 15酸性树脂已被证明是一种温和有效的活化剂，可用于与常用的脱甲糖基三氯乙酰亚氨酸酯供体进行糖基化反应。由Amberlyst 15促进的一组代表性醇和硫醇受体的糖基化，半乳糖基化，鼠李糖基化和乳糖基化可以中等至极好的产率形成结构多样的O或S联寡糖和糖基化氨基酸。
• <i>N</i>-Glycosyl Amides as Glycosyl Donors in Stereoselective Glycosylation Reactions
  作者：Horst Kunz、Norbert Pleuss

  DOI：10.1055/s-2004-834911

  日期：——

  Due to their high stability, N-glycosyl amides have so far not been considered as glycosyl donors for glycosylation reactions. Two new procedures for the cleavage of the anomeric amide functionality under mild reaction conditions and further stereoselective in situ conversions of the activated glycosyl donors with alcohols and amines to give β-configured O- and N-glycosides are described in this article

  由于它们的高稳定性，N-糖基酰胺迄今为止还没有被认为是糖基化反应的糖基供体。本文描述了在温和反应条件下裂解异头酰胺官能团的两种新程序，以及活化糖基供体与醇和胺的进一步立体选择性原位转化以产生 β-构型的 O-和 N-糖苷。
• Different reactivities of acetylated exo- and endo-cyanoethylidene derivatives in glycosylation reactions
  作者：Cristina Vicent、Jose-Miguel Coteron、Jesus Jimenez-Barbero、Manuel Martin-Lomas、Soledad Penades

  DOI：10.1016/0008-6215(89)85016-5

  日期：1989.12

  Abstract The condensation of acetylated 1-( endo -cyano)ethylidene derivatives having the d - gluco , d - xylo , and d - galacto configurations ( 2 – 6 ) with a primary ( 8 ) and a secondary ( 9 ) trityl derivative was more rapid than for the corresponding exo -isomers. This difference in reactivity is explained on the basis of differences in conformation.

  摘要具有d-葡萄糖，d-木糖和d-半乳糖构型（2-6）与伯（8）和仲（9）三苯甲基衍生物的乙酰化1-（内氰基）亚乙基衍生物的缩合反应较多。比相应的exo-异构体快。反应性的差异是根据构象差异来解释的。
• Fluoropyridyl Sugars – Masked Imidate Glycosyl Donors that Display Reactivity, Selectivity, and Stability
  作者：Ray Leslie、Kavnen Tseke、Agneta Vitkute、Sophie Benjamin、L. Seetohul

  DOI：10.1055/s-0036-1588478

  日期：2017.10

  from the corresponding glycosyl bromides, are shown to be excellent donors in glycosylation reactions. Both armed and disarmed donors were prepared and reacted smoothly with a series of glycosyl acceptors. Coupling proceeded in high yields, with activation of the donor achieved using a range of promoters, and also displayed unusually high selectivity. In addition these novel systems offer the potential

  由相应的糖基溴化物合成的氟吡啶基糖苷被证明是糖基化反应中的出色供体。准备好武装和解除武装的供体并与一系列糖基受体顺利反应。偶联以高产率进行，使用一系列启动子实现了供体的活化，并且还表现出异常高的选择性。此外，这些新系统提供了引入一系列具有“可调反应性”的糖基供体的潜力。
• 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。