methyl 2-O-benzyl-3-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)(1→3)-4,6-O-benzylidene-α-D-glucopyranoside | 203740-95-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2-O-benzyl-3-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)(1→3)-4,6-O-benzylidene-α-D-glucopyranoside
• 英文别名: methyl 2-O-benzyl-3-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-(1→3)-4,6-O-benzylidene-α-D-glucopyranoside；methyl (2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-(1→3)-2-O-benzyl-4,6-O-benzylidine-α-D-glucopyranoside；methyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl-(1->3)-2-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside；methyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl-(1→3)-2-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside；methyl 2-O-benzyl-3-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-4,6-O-benzylidene-α-D-glucopyranoside；methyl 2-O-benzyl-4,6-O-benzylidene-3-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-α-D-glucopyranoside
• CAS: 203740-95-8
• 化学式: C₅₅H₅₈O₁₁
• 分子量: 895.059
• InChiKey: IHHHSYRYEZHVEA-QRKVSYOJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.14
• 重原子数：
  66.0
• 可旋转键数：
  20.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  101.53
• 氢给体数：
  0.0
• 氢受体数：
  11.0

反应信息

• 作为产物：
  描述：

  氯 2,3,4,6-四-O-苄基-|á-D-吡喃葡萄糖苷 在 15-冠醚-5 、 3 A molecular sieve 、 silver trifluoromethanesulfonate 作用下， 以 1,2-二氯乙烷 、 乙腈 为溶剂， 反应 1.0h， 生成 methyl 2-O-benzyl-3-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)(1→3)-4,6-O-benzylidene-α-D-glucopyranoside
  参考文献：
  名称：

  高效，通用和稳定：噻唑基硫代糖苷作为糖基供体。

  摘要：

  DOI：

  10.1002/anie.200454047

文献信息

• An Air- and Water-Stable Iodonium Salt Promoter for Facile Thioglycoside Activation
  作者：An-Hsiang Adam Chu、Andrei Minciunescu、Vittorio Montanari、Krishna Kumar、Clay S. Bennett

  DOI：10.1021/ol5004059

  日期：2014.3.21

  iodonium salt phenyl(trifluoroethyl)iodonium triflimide is shown to activate thioglycosides for glycosylation at room temperature. Both armed and disarmed thioglycosides rapidly undergo glycosylation in 68–97% yield. The reaction conditions are mild and do not require strict exclusion of air and moisture. The operational simplicity of the method should allow experimentalists with a limited synthetic background

  空气和水稳定的碘鎓盐苯基（三氟乙基）碘鎓三氟甲磺酰亚胺在室温下可激活硫代糖苷以进行糖基化。武装和解除武装的硫糖苷都以 68-97% 的产率迅速进行糖基化。反应条件温和，不需要严格排除空气和水分。该方法的操作简单性应该允许具有有限合成背景的实验者构建糖苷键。
• Cooperative Catalysis in Glycosidation Reactions with<i>O</i>-Glycosyl Trichloroacetimidates as Glycosyl Donors
  作者：Yiqun Geng、Amit Kumar、Hassan M. Faidallah、Hassan A. Albar、Ibrahim A. Mhkalid、Richard R. Schmidt

  DOI：10.1002/anie.201302158

  日期：2013.9.16

  Thiourea mediates cooperative glycosidation through hydrogen bonding. N,N′‐Diarylthiourea as cocatalyst enforces an SN2‐type acid‐catalyzed glycosidation even at room temperature (see scheme; Bn=benzyl). From O‐(α‐glycosyl) trichloroacetimidates as glycosyl donors and various acceptors, β‐glycosides are preferentially or exclusively obtained.

  硫脲通过氢键介导协同糖基化。N，N'-二芳基硫脲作为助催化剂即使在室温下也可增强S N 2型酸催化的糖苷化作用（见方案； Bn =苄基）。从O-（α-糖基）三氯乙酰亚氨酸盐作为糖基供体和各种受体，可以优先或仅从中获得β-糖苷。
• Glycosylation Reactions Using Phenyl(trifluoroethyl)iodonium Salts
  申请人：Trustees of Tufts College

  公开号：US20150099870A1

  公开（公告）日：2015-04-09

  Provided are methods for the preparation of glycosylation products, including those represented by formula I: Sugar-O—R′  I comprising the step of combining R′—OH, a glycosyl sulfide glycosyl donor (“thioglycoside donor”), a hypervalent iodine alkyl-transfer activating reagent, and a base. In an embodiment, the hypervalent iodine alkyl-transfer activating reagent is (phenyl(trifluoroethyl)iodonium triflimide).

  提供了制备糖基化产物的方法，包括由式I表示的那些： 糖-O—R′  I 包括将R′—OH、糖基硫醚糖基供体（“硫代糖苷供体”）、高价碘烷基转移活化试剂和碱结合的步骤。在一种实施例中，高价碘烷基转移活化试剂为（苯基(三氟乙基)碘三氟甲磺酰胺）。
• Stereoselective Koenigs-Knorr Glycosylation Catalyzed by Urea
  作者：Lifeng Sun、Xiaowei Wu、De-Cai Xiong、Xin-Shan Ye

  DOI：10.1002/anie.201600142

  日期：2016.7.4

  A stereoselective Koenigs–Knorr glycosylation reaction under the catalysis of urea is described. This method is characterized by urea‐mediated hydrogen‐bond activation and subsequent glycosylation with glycosyl chlorides or bromides. Excellent yields and high anomeric selectivity can be achieved in most cases. Moreover, the low α‐stereoselectivity of glycosylations observed when using perbenzylated

  描述了在尿素催化下的立体选择性Koenigs-Knorr糖基化反应。该方法的特点是尿素介导的氢键活化以及随后与糖基氯化物或溴化物的糖基化作用。在大多数情况下，都可以实现出色的收率和高异头异构体选择性。此外，通过添加三（2,4,6-三甲氧基苯基）膦（TTMPP），可以大大改善使用过苄基葡萄糖基供体时观察到的低糖基化α-立体选择性。
• Glycosylation with 3,5-Dimethyl-4-(2′-phenylethynylphenyl)phenyl (EPP) Glycosides via a Dearomative Activation Mechanism
  作者：Zhifei Hu、Yu Tang、Biao Yu

  DOI：10.1021/jacs.9b00210

  日期：2019.3.27

  A highly effective and versatile glycosylation method is developed, which uses 3,5-dimethyl-4-(2'-phenylethynylphenyl)phenyl (EPP) glycosides as donors and NIS/TMSOTf as promoter and proceeds via an unprecedented dearomative activation mechanism.

  开发了一种高效且通用的糖基化方法，该方法使用 3,5-二甲基-4-(2'-苯基乙炔基苯基)苯基 (EPP) 糖苷作为供体，NIS/TMSOTf 作为启动子，并通过前所未有的脱芳基活化机制进行。