methyl 2,3,4-tri-O-benzyl-6-O-(tert-butyldiphenylsilyl)-β-D-glucopyranoside | 155044-88-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,3,4-tri-O-benzyl-6-O-(tert-butyldiphenylsilyl)-β-D-glucopyranoside
• 英文别名: methyl 6-O-tert-butyldiphenylsilyl-2,3,4-tri-O-benzyl-β-D-glucopyranoside；Methyl6-O-tert-butyldiphenylsilyl-2,3,4-tri-O-benzyl-β-D-glucopyranoside；Methyl 6-O-tert-butyldiphenylsilyl-2,3,4-tri-O-benzyl-beta-D-glucopyranoside；tert-butyl-[[(2R,3R,4S,5R,6R)-6-methoxy-3,4,5-tris(phenylmethoxy)oxan-2-yl]methoxy]-diphenylsilane
• CAS: 155044-88-5
• 化学式: C₄₄H₅₀O₆Si
• 分子量: 702.963
• InChiKey: GEYKFJRDKMXPMQ-BQLIBBPVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.69
• 重原子数：
  51
• 可旋转键数：
  16
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  55.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 2,3,4-tri-O-benzyl-6-O-(tert-butyldiphenylsilyl)-β-D-glucopyranoside 在 四丁基氟化铵 、 silver trifluoromethanesulfonate 、 1,1,3,3-四甲基脲 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 15.5h， 生成 methyl 6-O-(2,3,4,6-tetrakis-O-(p-bromobenzoyl)-β-D-glucopyranosyl)-2,3,4-tri-O-benzyl-β-D-glucopyranoside
  参考文献：
  名称：

  Hydroxymethyl Rotamer Populations in Disaccharides

  摘要：

  Sixteen methyl glucopyranosyl glucopyranoside disaccharides (methyl beta-D-Glcp(p-Br-Bz)-(1-->alpha)-beta/alpha-D-Glcp) containing beta-glycosidic linkages (1-->2, 1-->3, 1-->4, and 1-->6) were synthesized and analyzed by means of CD and NMR spectroscopy in three different solvents. For each of these four types of disaccharides, a correlation was observed between the hydroxymethyl rotational populations around the C5-C6 bond of the glucopyranosyl residue II with the substituents and the anomeric configuration of the methoxyl group in residue I, as well as with the solvent. Nonbonded interactions, the stereoelectronic exo-anomeric effect, and hydrogen bonding were found to be responsible for the observed rotameric differences. Whereas the rotational populations of the (1-->6)-linked disaccharides are mainly dependent on the exo-anomeric effect, the (1-->2)-bonded disaccharides are strongly dependent on the anomeric configuration at C1, and the (1-->3)- and (1-->4)-linked disaccharides are mainly dependent on the substituents and the solvent. The population of the gt rotamer decreases as nonbonded interactions increase but increases as the exo-anomeric effect becomes greater, as well as in the presence of intramolecular hydrogen bonding to the endocyclic oxygen O5'. Comparison of the hydroxymethyl rotational preferences between our model disaccharides revealed a dependence on the glycosidic linkage type. Thus the population of the gg and gt rotamers decreases/increases from (1-->2)-(beta series), to (1-->6)-, to (1-->2)-(alpha series), to (1-->4)-, and to (1-->3)-bonded disaccharides respectively, while the tg rotamer population remains almost constant (around 20%), except for the (1-->3)- and (1-->4)-linked disaccharides with the intramolecular hydrogen bonding to O5', where this population decreases to 10%.

  DOI：

  10.1021/jo026913o
• 作为产物：
  描述：

  甲基 Β-D-吡喃葡萄糖苷 在 咪唑 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 methyl 2,3,4-tri-O-benzyl-6-O-(tert-butyldiphenylsilyl)-β-D-glucopyranoside
  参考文献：
  名称：

  Hydroxymethyl Rotamer Populations in Disaccharides

  摘要：

  Sixteen methyl glucopyranosyl glucopyranoside disaccharides (methyl beta-D-Glcp(p-Br-Bz)-(1-->alpha)-beta/alpha-D-Glcp) containing beta-glycosidic linkages (1-->2, 1-->3, 1-->4, and 1-->6) were synthesized and analyzed by means of CD and NMR spectroscopy in three different solvents. For each of these four types of disaccharides, a correlation was observed between the hydroxymethyl rotational populations around the C5-C6 bond of the glucopyranosyl residue II with the substituents and the anomeric configuration of the methoxyl group in residue I, as well as with the solvent. Nonbonded interactions, the stereoelectronic exo-anomeric effect, and hydrogen bonding were found to be responsible for the observed rotameric differences. Whereas the rotational populations of the (1-->6)-linked disaccharides are mainly dependent on the exo-anomeric effect, the (1-->2)-bonded disaccharides are strongly dependent on the anomeric configuration at C1, and the (1-->3)- and (1-->4)-linked disaccharides are mainly dependent on the substituents and the solvent. The population of the gt rotamer decreases as nonbonded interactions increase but increases as the exo-anomeric effect becomes greater, as well as in the presence of intramolecular hydrogen bonding to the endocyclic oxygen O5'. Comparison of the hydroxymethyl rotational preferences between our model disaccharides revealed a dependence on the glycosidic linkage type. Thus the population of the gg and gt rotamers decreases/increases from (1-->2)-(beta series), to (1-->6)-, to (1-->2)-(alpha series), to (1-->4)-, and to (1-->3)-bonded disaccharides respectively, while the tg rotamer population remains almost constant (around 20%), except for the (1-->3)- and (1-->4)-linked disaccharides with the intramolecular hydrogen bonding to O5', where this population decreases to 10%.

  DOI：

  10.1021/jo026913o

文献信息

• Non-peptide peptidomimetics and related cyclic hexapeptides
  申请人：The Trustees of the University of Pennsylvania

  公开号：US05811512A1

  公开（公告）日：1998-09-22

  Compounds are provided which are crossreactive with peptides such as those which bind G-protein-linked receptors, together with preparative and therapeutic methods therefor.

  提供的化合物与那些结合G蛋白偶联受体的肽具有交叉反应性，以及用于这些化合物的制备和治疗方法。
• Non-Peptide peptidomimetics
  申请人：The Trustees of the University of Pennsylvania

  公开号：US05552534A1

  公开（公告）日：1996-09-03

  Compounds are provided which are crossreactive with peptides such as those which bind G-protein-linked receptors, together with preparative and therapeutic methods therefor. The compounds have the general structure: ##STR1## wherein at least one of R.sub.1, R.sub.2, R.sub.3, R.sub.4, or R.sub.5 comprises a functional group which is chemically similar to that found in the peptide of interest.

  提供了与肽交叉反应的化合物，例如那些与G蛋白偶联受体结合的肽，以及相应的制备和治疗方法。这些化合物具有一般结构：##STR1##其中至少有一个R.sub.1、R.sub.2、R.sub.3、R.sub.4或R.sub.5包括与感兴趣的肽中发现的化学相似的官能团。
• Non-peptide peptidomimetics
  申请人：The Trustees of the University of Pennsylvania

  公开号：US06197963B1

  公开（公告）日：2001-03-06

  Compounds are provided which are crossreactive with peptides such as those which bind G-protein-linked receptors, together with preparative and therapeutic methods therefor. The compounds have the general structure: wherein at least one of R1, R2, R3, R4, or R5 comprises a functional group which is chemically similar to that found in the peptide of interest.

  提供了与结合G蛋白偶联受体的肽交叉反应的化合物，以及其制备和治疗方法。这些化合物具有以下一般结构：其中R1、R2、R3、R4或R5中至少有一个包含与感兴趣的肽中发现的化学相似的功能基团。
• Rapid access to organic triflates based on flash generation of unstable sulfonium triflates in flow
  作者：Masahiro Takumi、Hodaka Sakaue、Daiki Shibasaki、Aiichiro Nagaki

  DOI：10.1039/d2cc02344j

  日期：——

  Flash (extremely fast) electrolysis in flow realized rapid generation of highly unstable arylbis(arylthio)sulfonium triflates, enabling one-flow access to vinyl triflates, short-lived oxocarbenium triflates and glycosyl triflates.

  在流动条件下进行的极快速电解制备高度不稳定的芳基双(芳硫基)硫鎓三氟甲烷磺酸盐，实现了对乙烯基三氟甲烷磺酸盐、短寿命的氧代碳鎓三氟甲烷磺酸盐和糖基三氟甲烷磺酸盐的一次流动访问。
• Hydroxymethyl Rotamer Populations in Disaccharides
  作者：Alfredo Roën、Juan I. Padrón、Jesús T. Vázquez

  DOI：10.1021/jo026913o

  日期：2003.6.1

  Sixteen methyl glucopyranosyl glucopyranoside disaccharides (methyl beta-D-Glcp(p-Br-Bz)-(1-->alpha)-beta/alpha-D-Glcp) containing beta-glycosidic linkages (1-->2, 1-->3, 1-->4, and 1-->6) were synthesized and analyzed by means of CD and NMR spectroscopy in three different solvents. For each of these four types of disaccharides, a correlation was observed between the hydroxymethyl rotational populations around the C5-C6 bond of the glucopyranosyl residue II with the substituents and the anomeric configuration of the methoxyl group in residue I, as well as with the solvent. Nonbonded interactions, the stereoelectronic exo-anomeric effect, and hydrogen bonding were found to be responsible for the observed rotameric differences. Whereas the rotational populations of the (1-->6)-linked disaccharides are mainly dependent on the exo-anomeric effect, the (1-->2)-bonded disaccharides are strongly dependent on the anomeric configuration at C1, and the (1-->3)- and (1-->4)-linked disaccharides are mainly dependent on the substituents and the solvent. The population of the gt rotamer decreases as nonbonded interactions increase but increases as the exo-anomeric effect becomes greater, as well as in the presence of intramolecular hydrogen bonding to the endocyclic oxygen O5'. Comparison of the hydroxymethyl rotational preferences between our model disaccharides revealed a dependence on the glycosidic linkage type. Thus the population of the gg and gt rotamers decreases/increases from (1-->2)-(beta series), to (1-->6)-, to (1-->2)-(alpha series), to (1-->4)-, and to (1-->3)-bonded disaccharides respectively, while the tg rotamer population remains almost constant (around 20%), except for the (1-->3)- and (1-->4)-linked disaccharides with the intramolecular hydrogen bonding to O5', where this population decreases to 10%.