phenyl 2,3,4-tri-O-benzyl-1-thio-6-O-trityl-β-D-galactopyranoside | 259871-03-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: phenyl 2,3,4-tri-O-benzyl-1-thio-6-O-trityl-β-D-galactopyranoside
• CAS: 259871-03-9
• 化学式: C₅₂H₄₈O₅S
• 分子量: 785.016
• InChiKey: IILPYWOFUQYONX-SVASUFRFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.27
• 重原子数：
  58.0
• 可旋转键数：
  17.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  46.15
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  phenyl 2,3,4-tri-O-benzyl-1-thio-6-O-trityl-β-D-galactopyranoside 在 甲基三辛基氯化铵 N-碘代丁二酰亚胺 、 重铬酸吡啶 、 三氟甲磺酸 、 Amberlyst 15 H⁺ 、 乙酸酐 、 四丁基碘化铵 、 碳酸氢钠 、 三氟乙酸 作用下， 以 乙醚 、 二氯甲烷 、 氯仿 、 水 为溶剂， 反应 8.5h， 生成 methyl (benzyl 2,3,4-tri-O-benzyl-α-D-galactopyranosyluronate)-(1->4)-(benzyl 2,3-di-O-benzyl-β-D-galactopyranosid)uronate
  参考文献：
  名称：

  二糖4-O-α-D-半乳糖醛糖基-D-半乳糖醛酸的两种单甲酯的合成，以及用于制备在一定序列中被乌龙酸酯化的高级低聚物的前体的合成。

  摘要：

  甲基（α-D-吡喃半乳糖醛酸）-（1-> 4）-D-吡喃半乳糖醛酸和甲基α-D-吡喃半乳糖基-尿酸-（1-> 4）-D-吡喃半乳糖醛酸通过偶联甲基（苄基2,3-二-O-苄基-β-D-吡喃半乳糖苷）尿酸酯（3）或苄基（苄基2,3-二-O-苄基-β-D-吡喃半乳糖苷）尿酸酯（4）与苄基（苯基2 ，3,4-三-O-苄基-1-硫代-β-D-吡喃半乳糖苷）尿酸和（苯基2,3,4-三-O-苄基-1-硫代-β-D-吡喃半乳糖苷）尿酸，分别使用N-碘琥珀酰亚胺和三氟甲磺酸作为促进剂，然后除去苄基。4'-OH未保护的二聚体苄基（2,3-二-O-苄基-α-D-吡喃半乳糖苷）（---> 4）-（苄基2,3-二-O-苄基-β-D -galactopyranosid）尿酸盐和（2,3-di-O-苄基-alpha-D-galactopyranosyluronate）甲基-（1-> 4）由（苯基2，3-二-O-苄基-1

  DOI：

  10.1016/s0008-6215(98)00312-7
• 作为产物：
  描述：

  苯基-1-硫醇-beta-D-半乳糖苷 在 吡啶 、 咪唑 、 4-二甲氨基吡啶 、 四丁基碘化铵 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 76.0h， 生成 phenyl 2,3,4-tri-O-benzyl-1-thio-6-O-trityl-β-D-galactopyranoside
  参考文献：
  名称：

  二糖4-O-α-D-半乳糖醛糖基-D-半乳糖醛酸的两种单甲酯的合成，以及用于制备在一定序列中被乌龙酸酯化的高级低聚物的前体的合成。

  摘要：

  甲基（α-D-吡喃半乳糖醛酸）-（1-> 4）-D-吡喃半乳糖醛酸和甲基α-D-吡喃半乳糖基-尿酸-（1-> 4）-D-吡喃半乳糖醛酸通过偶联甲基（苄基2,3-二-O-苄基-β-D-吡喃半乳糖苷）尿酸酯（3）或苄基（苄基2,3-二-O-苄基-β-D-吡喃半乳糖苷）尿酸酯（4）与苄基（苯基2 ，3,4-三-O-苄基-1-硫代-β-D-吡喃半乳糖苷）尿酸和（苯基2,3,4-三-O-苄基-1-硫代-β-D-吡喃半乳糖苷）尿酸，分别使用N-碘琥珀酰亚胺和三氟甲磺酸作为促进剂，然后除去苄基。4'-OH未保护的二聚体苄基（2,3-二-O-苄基-α-D-吡喃半乳糖苷）（---> 4）-（苄基2,3-二-O-苄基-β-D -galactopyranosid）尿酸盐和（2,3-di-O-苄基-alpha-D-galactopyranosyluronate）甲基-（1-> 4）由（苯基2，3-二-O-苄基-1

  DOI：

  10.1016/s0008-6215(98)00312-7

文献信息

• In(III) triflate-catalyzed detritylation and glycosylation by solvent-free ball milling
  作者：Vajinder Kumar、Narender Yadav、K.P. Ravindranathan Kartha

  DOI：10.1016/j.carres.2014.08.002

  日期：2014.10

  A highly efficient In(III) triflate-assisted method for the detritylation of O-trityl derivatives of carbohydrates, phenols, and alcohols using solvent-free mechanochemical method is described. In the case of carbohydrates, further reaction in the presence of an acceptor sugar leads to highly efficient glycosylation in the same pot resulting in the formation of the desired glycoside-product in very high yields. The method was applied successfully to the synthesis of a combinatorial library of galactose-based (1,6)-linked cyclo-hexa-, hepta-, and octasaccharides on gram scale. (C) 2014 Elsevier Ltd. All rights reserved.
• Stereodirecting Effect of the Pyranosyl C-5 Substituent in Glycosylation Reactions
  作者：Jasper Dinkelaar、Ana Rae de Jong、Robert van Meer、Mark Somers、Gerrit Lodder、Herman S. Overkleeft、Jeroen D. C. Codée、Gijsbert A. van der Marel

  DOI：10.1021/jo900662v

  日期：2009.7.17

  The stereodirecting effect of the glycosyl C-5 substituent has been investigated in a series of D-pyranosyl thioglycoside donors and related to their preferred positions in the intermediate H-3(4) and H-4(3) half-chair oxacarbenium ions. Computational studies showed that an axially positioned C-5 carboxylate ester can stabilize the (3)H4 half-chair oxacarbenium ion conformer by donating electron densit from its carbonyl function into the electron-poor oxacarbenium ion functionality. A similar stabilization can be achieved by a C-5 benzyloxyrnethyl group, but,the magnitude of this stabilization is significantly smaller than for the C-5 carboxylate ester. As a result, the preference of the C-5 benzyloxymethyl to occupy an axial position in the half-chair oxacarbenium ions is much reduced compared to the C-5 carboxylate ester. To minimize steric interactions, a C-5 methyl group prefers to adopt an equatorial position and therefore favors the H-4(3) half-chair oxacarbenium ion. When all pyranosyl substituents occupy their favored position in one of the two intermediate half-chair oxacarbenium ions, highly stereoselective glycosylations can be achieved as revealed by the excellent beta-selectivity of mannuronate esters and alpha-selectivity of 6-deoxygulosides.
• Prearranged Glycosides. Part 8. Intramolecular α-Galactosylation Via Succinoyl Tethered Glycosides
  作者：Thomas Ziegler、Ralf Dettmann、Ariffadhillah、Uwe Zettl

  DOI：10.1080/07328309908544056

  日期：1999.1

  Benzyl protected phenyl 1-thio-galactopyranoside donors which were tethered by a succinoyl linker at their positions 2 and 6, respectively, to position 3 of a blocked benzyl glucopyranoside acceptor with a 4-OH group solely afforded the corresponding alpha-(1-->4)-linked disaccharides upon intramolecular glycosylation. 4,6-Siloxane protected mannosides react with rearrangement of the siloxane group under similar conditions.