methyl O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-(1->6)-2,3,4-tri-O-benzyl-β-D-glucopyranoside | 108739-69-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-(1->6)-2,3,4-tri-O-benzyl-β-D-glucopyranoside
• 英文别名: methyl 2,3,4,6-tetra-O-benzyl-D-glucopyranosyl-(1→6)-2,3,4-tri-O-benzyl-β-D-glucopyranoside；methyl O-(2,3,4,6-tetra-O-benzyl-p-D-glucopyranosyl)-(1->6)-2,3,4-tri-O-benzyl-D-glucopyranoside；Bn(-2)[Bn(-3)][Bn(-4)][Bn(-6)]Glc(b1-6)[Bn(-2)][Bn(-3)][Bn(-4)]b-Glc1Me；(2R,3R,4S,5R,6R)-2-methoxy-3,4,5-tris(phenylmethoxy)-6-[[(2R,3R,4S,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxymethyl]oxane
• CAS: 108739-69-1
• 化学式: C₆₂H₆₆O₁₁
• 分子量: 987.199
• InChiKey: FLOIPOSVHDNCRB-MXSXRUIZSA-N

物化性质

• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.5
• 重原子数：
  73
• 可旋转键数：
  26
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  102
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  methyl 6-O-allyloxycarbonyl-2,3,4-tri-O-benzyl-α-D-glucopyranoside 在 [Bu₄N][Fe(CO)3(NO)] 、 三异丙叉丙酮基膦 、 异丙硫醇 作用下， 以 乙醇 为溶剂， 反应 15.0h， 生成 methyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl-(1-6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside 、 methyl O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-(1->6)-2,3,4-tri-O-benzyl-β-D-glucopyranoside
  参考文献：
  名称：

  轻度无配体铁催化从烯丙基碳酸酯中解醇

  摘要：

  与大多数碳酸盐不同，烯丙氧基羰基保护基可以在中性条件下使用金属催化裂解。然而，迄今为止使用的大多数催化剂是基于贵金属的。本文中，我们提出了两种温和的铁催化从烯丙基碳酸酯中释放醇的方案，其特征在于宽泛的官能团耐受性和独有的化学选择性。

  DOI：

  10.1021/ol202270g

文献信息

• Dehydrative Glycosylation by Diethylaminosulfur Trifluoride (DAST)–Tin(II) Trifluoromethanesulfonate–Tetrabutylammonium Perchlorate–Triethylamine System
  作者：Motoko Hirooka、Shinkiti Koto

  DOI：10.1246/bcsj.71.2893

  日期：1998.12

  Dehydrative glycosylation using 2,3,4,6-tetra-O-benzyl-D-glucopyranose was carried out by the use of a condensing reagent system composed of diethylaminosulfur trifluoride (DAST), tin(II) triflate, tetrabutylammonium perchlorate, and triethylamine. Using this system, two tetrasaccharides, O-α-D-glucopyranosyl-(1→4)-O-α-D-glucopyranosyl-(1→3)-O-α-D-glucopyranosyl-(1→4)-D-glucopyranose and O-α-D-glu

  通过使用由二乙氨基三氟化硫 (DAST)、三氟甲磺酸锡 (II)、四丁基高氯酸铵和三乙胺组成的缩合试剂系统，使用 2,3,4,6-四-O-苄基-D-吡喃葡萄糖进行脱水糖基化. 使用该系统，两种四糖，O-α-D-吡喃葡萄糖基-(1→4)-O-α-D-吡喃葡萄糖基-(1→3)-O-α-D-吡喃葡萄糖基-(1→4)-D -吡喃葡萄糖和 O-α-D-吡喃葡萄糖基-(1→3)-O-α-D-吡喃葡萄糖基-(1→4)-O-α-D-吡喃葡萄糖基-(1→4)-D-吡喃葡萄糖合成的。
• Glycosylation with Disarmed Glycosyl Bromides Promoted by Iodonium Ions
  作者：Gyrithe Lanz、Robert Madsen

  DOI：10.1002/ejoc.201600545

  日期：2016.6

  Iodonium ions have been developed for activating glycosyl bromides in the coupling to glycosyl acceptors. The iodonium ions are generated from N-iodosuccinimide and a protic acid such as camphorsulfonic acid or triflic acid, where the latter gives the most reactive promoter system. The couplings occur with the release of iodine monobromide, and the best results are obtained with benzoylated glycosyl

  碘鎓离子已被开发用于激活与糖基受体偶联的糖基溴化物。碘鎓离子由 N-碘代琥珀酰亚胺和质子酸（如樟脑磺酸或三氟甲磺酸）产生，其中后者提供最具反应性的促进剂系统。偶联随着一溴化碘的释放而发生，使用苯甲酰化糖基供体和受体获得最佳结果。通过这种方式，去武装的糖基溴化物可以作为糖基供体，而无需使用重金属盐。
• Synthesis of 1,2--linked glycosides using dimethyl(methylthio) sulfonium triplate as promoter and thioglycosides as glycosyl donors
  作者：Fredrik Andersson、Péter Fúgedi、Per J. Garegg、Mina Nashed

  DOI：10.1016/s0040-4039(00)83917-9

  日期：1986.1

  Stereoselective, halide-assisted, 1,2-cis-glycosylations may be obtained using stable thioglycosides containing a non-participating 2-substituent as glycosyl donors, in the presence of dimethyl(methythio)sulfonium triflate and tetrabutylammonium bromide as promoters.

  在三氟甲磺酸二甲基（甲硫基）s和四丁基溴化铵作为促进剂的情况下，使用含有非参与性2-取代基的稳定硫代糖苷作为糖基供体，可以得到立体选择性的，卤化物辅助的1,2-顺式糖基化。
• Metallocene bis(perfluoroalkanesulfonate)s as air-stable cationic Lewis acids
  作者：Renhua Qiu、Guoping Zhang、Xinhua Xu、Kangbin Zou、Lingling Shao、Dawei Fang、Yinhui Li、Akihiro Orita、Ryosuke Saijo、Hidetaka Mineyama、Tomoyoshi Suenobu、Shunichi Fukuzumi、Delie An、Junzo Otera

  DOI：10.1016/j.jorganchem.2008.12.057

  日期：2009.4

  Zirconocene and titanocene bis(perfluorooctanesulfonate)s were synthesized. In contrast to the corresponding triflates and perchlorates, these compounds are air- and water-stable. They were proved to be ionic on the basis of conductivity measurements and X-ray analysis, allowing these complexes to be stored for months. The strong Lewis acidity of these cationic metallocene species, which was proved by ESR study, enabled catalytic glycosylation. (c) 2009 Elsevier B.V. All rights reserved.
• ANDERSSON, FREDRIK O., CHEM. COMMUN./UNIV. STOCKHOLM.,(1989) N, C. 1-33
  作者：ANDERSSON, FREDRIK O.

  DOI：——

  日期：——