methyl 2,3,4-tri-O-benzyl-6-O-(2,3,4-tri-O-benzyl-β-D-glucopyranosyl)-α-D-glucopyranoside | 76679-49-7

• 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-(2,3,4-tri-O-benzyl-β-D-glucopyranosyl)-α-D-glucopyranoside
• 英文别名: methyl 2,3,4-tri-O-benzyl-β-D-glucopyranosyl-(1->6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside；methyl 2,3,4-tri-O-benzyl-6-O-(2',3',4'-tri-O-benzyl-β-D-glucopyranosyl)-1-α-D-glucopyranoside；Bn(-2)[Bn(-3)][Bn(-4)]Glc(b1-6)[Bn(-2)][Bn(-3)][Bn(-4)]a-Glc1Me；[(2R,3R,4S,5R,6R)-6-[[(2R,3R,4S,5R,6S)-6-methoxy-3,4,5-tris(phenylmethoxy)oxan-2-yl]methoxy]-3,4,5-tris(phenylmethoxy)oxan-2-yl]methanol
• CAS: 76679-49-7
• 化学式: C₅₅H₆₀O₁₁
• 分子量: 897.075
• InChiKey: BWEYUPJLUVTHLY-RKRLIWQFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  66
• 可旋转键数：
  23
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  113
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  methyl 2,3,4-tri-O-benzyl-6-O-(2,3,4-tri-O-benzyl-β-D-glucopyranosyl)-α-D-glucopyranoside 在 钯 氢气 作用下， 以97%的产率得到methyl 6-O-(β-D-glucopyranosyl)-α-D-glucopyranoside
  参考文献：
  名称：

  通过1-0-烷基化合成α-和β-吡喃葡萄糖苷

  摘要：

  部分保护的吡喃葡萄糖1和半乳糖吡喃糖13的1-0烷基化导致β-糖苷和β-二糖4a-d和14的便捷，短期合成。在0-6带有较大保护基的葡糖醛糖2仅产生α。 -异头物（异麦芽糖苷衍生物）5。

  DOI：

  10.1016/0040-4039(80)80236-x
• 作为产物：
  描述：

  methyl 2,3,4-tri-O-benzyl-6-O-(2,3,4-tri-O-benzyl-6-O-picoloyl-β-D-glucopyranosyl)-α-D-glucopyranoside 在 copper diacetate 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 生成 methyl 2,3,4-tri-O-benzyl-6-O-(2,3,4-tri-O-benzyl-β-D-glucopyranosyl)-α-D-glucopyranoside
  参考文献：
  名称：

  绕过糖基卤化物中间体的硫代糖苷协同催化活化

  摘要：

  报道了一种无需糖基卤化物中间体、使用银盐与酸添加剂和分子碘偶联来活化硫代糖苷的新方法。氢键介导的糖苷配基递送（HAD）方法的应用增强了立体控制。

  DOI：

  10.1002/chem.202300873

文献信息

• Low-Concentration 1,2-<i>trans</i>β-Selective Glycosylation Strategy and Its Applications in Oligosaccharide Synthesis
  作者：Chin-Sheng Chao、Chen-Wei Li、Min-Chun Chen、Shih-Sheng Chang、Kwok-Kong Tony Mong

  DOI：10.1002/chem.200901119

  日期：2009.10.19

  This study develops an operationally easy, efficient, and general 1,2‐trans β‐selective glycosylation reaction that proceeds in the absence of a C2 acyl function. This process employs chemically stable thioglycosyl donors and low substrate concentrations to achieve excellent β‐selectivities in glycosylation reactions. This method is widely applicable to a range of glycosyl substrates irrespective of

  这项研究开发了一种易于操作，有效且通用的1,2-反式β-选择性糖基化反应，该反应在没有C2酰基功能的情况下进行。该过程采用化学上稳定的硫糖基供体和低底物浓度，以在糖基化反应中实现出色的β选择性。该方法可广泛应用于各种糖基底物，无论其结构和羟基保护功能如何。碳水化合物化学中这种低浓度的1,2-反式β-选择性糖基化消除了使用高反应性硫糖苷构建1,2-反式的限制β糖苷键。这有利于寡糖合成新策略的设计，如生物学相关的β-（1→6）-葡聚糖三糖，β-连接的Gb 3和isoGb 3衍生物的制备所示。
• Novel alpha-glucosidase inhibitors
  申请人：MERRELL DOW PHARMACEUTICALS INC.

  公开号：EP0389723A1

  公开（公告）日：1990-10-03

  This invention relates to novel N-derivatives, of 1,4-di-­deoxy-1,4-imino-L-arabinitol (I), to the processes for their preparation and to their end-use applications, particularly as to their use in the treatment of diabetes. wherein n is zero, one or two, and R is a glycosyl or etherified or acylated glycosyl radical containing from 1 to 3 hexose or pentose units, said glycosyl radical optionally bearing an ether or ester derivative of the hydroxyl moiety located on the anomeric carbon atom.

  本发明涉及新颖的1,4-二脱氧-1,4-亚氨基-L-阿拉伯糖醇（I）的N-衍生物，涉及其制备方法及其最终用途，特别是作为治疗糖尿病的用途。 其中n为0、1或2，R为含有1至3个己糖或戊糖单元的糖基或醚化或酰化的糖基基团，所述糖基基团任选地在其异头碳原子上的羟基部分带有醚或酯衍生物。
• Synthesis, glycosylation and photolysis of photolabile 2-(2-nitrophenyl)propyloxycarbonyl (NPPOC) protected glycopyranosides
  作者：Hua Yi、Stéphane Maisonneuve、Juan Xie

  DOI：10.1039/b908404e

  日期：——

  The photolabile NPPOC group has been successfully introduced into the 6-position of various glycopyranosides in 91–97% yield. Glycosylation of NPPOC-protected phenyl β-D-thiogluco- and galactopyranosides with appropriate acceptors afforded the corresponding disaccharides in good yield. Excellent β-stereoselectivity (β/α≥ 10/1) can be obtained when the glycosylation was realized in CH3CN at −40 °C. Furthermore, the 6-O-NPPOC thioglucoside 6 can also be readily converted into the corresponding glucopyranose or glucosyl fluoride. The photolysis of 6-O-NPPOC diacetone D-galactose 4 has been studied by UV–vis absorption in CH3CN in the presence of water or DBU at 365 nm. At 100 µM concentration, photocleavage of 4 was accomplished after 5 min irradiation, with t1/2 = 37 s (10% water), 75 s (1 equiv. DBU) or 87 s (0.05 M DBU). The formation of the nitroso byproduct can be avoided in the presence of 0.05 M DBU. All the NPPOC-protected mono- or disaccharides can be readily removed by photolysis at 365 nm in CH3CN the presence of water or DBU in more than 87% yield.

  光敏性NPPOC基团成功引入到各种糖吡喃苷的6位，以91–97%的产率合成。用适当的受体对NPPOC保护的苯基β-D-硫葡萄糖苷和半乳糖苷进行糖苷化反应，可以良好产出相应的二糖。在−40 °C的CH3CN中进行糖苷化反应时，获得了优良的β立体选择性（β/α≥ 10/1）。此外，6-O-NPPOC硫葡萄糖苷6也可以方便地转化为相应的葡萄糖吡喃糖或葡萄糖基氟化物。对6-O-NPPOC二乙酮D-半乳糖4的光解研究显示，在CH3CN中存在水或DBU的条件下，在365 nm照射下进行。以100 µM的浓度，在5分钟的照射后实现了对4的光裂解，半衰期分别为37秒（10%水）、75秒（1当量DBU）或87秒（0.05 M DBU）。在0.05 M DBU存在的情况下，可以避免亚硝基副产物的形成。所有NPPOC保护的单糖或二糖都可以通过在CH3CN中以365 nm的波长光解，并在水或DBU存在下去除，产率超过87%。
• Novel alpha-Glucosidase inhibitors
  申请人：MERRELL DOW PHARMACEUTICALS INC.

  公开号：EP0344383A1

  公开（公告）日：1989-12-06

  This invention relates to novel N-derivatives of 1-deoxy-nojirimyoin, to the processes for their preparation and to their end-use applications, particularly as to their use in the treatment of diabetes.

  本发明涉及 1-脱氧野尻yoin的新型 N-衍生物、其制备工艺及其最终用途，特别是在治疗糖尿病方面的应用。
• 6-<i>O</i>-Picolinyl and 6-<i>O</i>-Picoloyl Building Blocks As Glycosyl Donors with Switchable Stereoselectivity
  作者：Abhijeet K. Kayastha、Xiao G. Jia、Jagodige P. Yasomanee、Alexei V. Demchenko

  DOI：10.1021/acs.orglett.5b02110

  日期：2015.9.18

  Remote 6-O-picolinyl or 6-O-picoloyl substituents often provide high beta-selectivity due to H-bond-mediated aglycone delivery (HAD). Herein it has been demonstrated that if the nitrogen atom of the 6-O-picolinyl or picoloyl moiety is temporarily blocked by coordination to a metal center (Pd), it cannot engage in HAD-mediated beta-glycosylation. Hence, the stereoselectivity of 6-O-picolinyl/picoloyl-assisted glycosylations can be "switched" to alpha-selectivity.