4-methoxyphenyl 2,3-O-isopropylidene β-D-xylopyranoside | 475101-58-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-methoxyphenyl 2,3-O-isopropylidene β-D-xylopyranoside
• 英文别名: (3aR,4S,7R,7aS)-4-(4-methoxyphenoxy)-2,2-dimethyl-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-7-ol
• CAS: 475101-58-7
• 化学式: C₁₅H₂₀O₆
• 分子量: 296.32
• InChiKey: YDYCZSVZPLBZKC-RQJABVFESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  66.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-methoxyphenyl 2,3-O-isopropylidene β-D-xylopyranoside 在 (1,5-cyclooctadiene)[bis(methyldiphenylphosphine)]iridium(I) hexafluorophosphate 吡啶 、 三氟甲磺酸三甲基硅酯 、 MSAW₃₀₀ 、 camphor-10-sulfonic acid 、 氢气 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 生成 4-methoxyphenyl O-(2,4,6-tri-O-acetyl-β-D-galactopyranosyl)-(1->3)-O-(2,4,6-tri-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3-di-O-(4-methylbenzoyl)-β-D-xylopyranoside
  参考文献：
  名称：

  Synthesis of betaglycan-type tetraosyl hexapeptide: a possible precursor regulating enzymatic elongation toward heparin

  摘要：

  Tetraosyl hexapeptide, a part of the sequence of betaglycan: beta-D-GlcA-(1-->3)-beta-D-Gal-(1-->3)-beta-D-Gal-(1-->4)-beta-D-Xyl-(1-->O-SerGlyTrpProAspGly (1), which was designed as a probe for glycan elongation toward heparin, was synthesized in a stereocontrolled manner. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00327-x
• 作为产物：
  描述：

  tetra-O-acetyl-β-D-xylopyranose 在 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 、 camphor-10-sulfonic acid 、 三乙胺 作用下， 以 甲醇 、 水 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 4-methoxyphenyl 2,3-O-isopropylidene β-D-xylopyranoside
  参考文献：
  名称：

  Synthetic Approach Toward the Partial Sequences of Betaglycan in the Linkage Region on Solid Support and in Solution Phase

  摘要：

  We have synthesized, for the first time, the partial sequence of the betaglycan composed of the tetraosyl hexapeptide, which was directly usable as a probe for enzymatic glycosyl transfer. Stepwise elongation afforded the corresponding tetraosyl trichloroacetimidate. The common glycosyl dipeptide:[beta-D-GlcA-(1 -> 3)-beta-D-Gal-(1 -> 3)-beta-D-Gal-(1 -> 4)-beta-D- Xyl-(1 -> O)-Ser-Gly] was synthesized by glycosylation of the corresponding tetraosyl trichloroacetimidate and Ser-Gly moiety. The glycosyl dipeptide was coupled with other core peptide parts in solution phase and on a solid support. These glycosyl hexapeptides were then transformed into the desired target compounds.

  DOI：

  10.1080/07328300701296810

文献信息

• Total Synthesis of <i>Pseudomonas aeruginosa</i> 1244 Pilin Glycan via <i>de Novo</i> Synthesis of Pseudaminic Acid
  作者：Han Liu、Yanfeng Zhang、Ruohan Wei、Gloria Andolina、Xuechen Li

  DOI：10.1021/jacs.7b06055

  日期：2017.9.27

  synthesis involve the diastereoselective glycine thioester isonitrile-based aldol-type reaction to create the 1,3-anti-diamino skeleton, followed by the Fukuyama reduction and the indium-mediated Barbier-type allylation. Moreover, we have studied the glycosylation of the Pse glycosyl donors and identified the structural determinants for its glycosylation diastereoselectivity, which enabled us to complete

  假胺酸 (Pse) 是细菌物种特有的一种非洛糖酸，是各种病原体物种中重要的细胞表面聚糖和糖蛋白的组成部分，例如对医院造成严重威胁的铜绿假单胞菌 (Pseudomonas aeruginosa)。在此，我们介绍了从容易获得的 Cbz-l-异素苏氨酸甲酯（16 个步骤，产率 11%）开发 Pse 及其功能化衍生物的简便且可扩展的从头合成。我们从头合成中的关键反应涉及基于非对映选择性甘氨酸硫酯异腈的羟醛型反应，以创建 1,3-抗二氨基骨架，然后是 Fukuyama 还原和铟介导的 Barbier 型烯丙基化。此外，我们研究了 Pse 糖基供体的糖基化，并确定了其糖基化非对映选择性的结构决定因素，
• The first total synthesis of rebaudioside R
  作者：Guo-En Wen、Zhi Qiao、Hui Liu、Zhi-Yong Zeng、Yuan-Hong Tu、Jian-Hui Xia、Qing-Ju Zhang、Jian-Song Sun

  DOI：10.1039/c9ob02422k

  日期：——

  and steviol as starting materials, the first total synthesis of rebaudioside R with a xylosyl core in the C13-OH linked sugar chain was accomplished via two distinct approaches. The first approach features the stepwise installation of branch-sugar residues via an order of C2-OH first and then C3-OH of the xylosyl core, laying a firm foundation for the synthesis of analogues with different branch sugars

  以容易获得的单糖和甜菊醇为原料，通过两种不同的方法完成了在C13-OH连接的糖链中具有木糖基核心的莱鲍迪苷R的首次全合成。第一种方法的特征是首先通过木糖基核心的C2-OH然后C3-OH的顺序逐步安装分支糖残基，为合成具有不同分支糖的类似物奠定了坚实的基础，而第二种方法的特征是通过融合策略引入C13三糖糖链，确保了整体合成效率。通过综合研究，说明了邻羟基上的保护基（PGs）对OH受体反应性的影响。
• Synthesis of betaglycan-type tetraosyl hexapeptide: a possible precursor regulating enzymatic elongation toward heparin
  作者：Jun-ichi Tamura、Akihiro Yamaguchi、Junko Tanaka

  DOI：10.1016/s0960-894x(02)00327-x

  日期：2002.8

  Tetraosyl hexapeptide, a part of the sequence of betaglycan: beta-D-GlcA-(1-->3)-beta-D-Gal-(1-->3)-beta-D-Gal-(1-->4)-beta-D-Xyl-(1-->O-SerGlyTrpProAspGly (1), which was designed as a probe for glycan elongation toward heparin, was synthesized in a stereocontrolled manner. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Synthetic Approach Toward the Partial Sequences of Betaglycan in the Linkage Region on Solid Support and in Solution Phase
  作者：Jun‐ichi Tamura、Akihiro Yamaguchi、Junko Tanaka、Yuko Nishimura

  DOI：10.1080/07328300701296810

  日期：2007.4.30

  We have synthesized, for the first time, the partial sequence of the betaglycan composed of the tetraosyl hexapeptide, which was directly usable as a probe for enzymatic glycosyl transfer. Stepwise elongation afforded the corresponding tetraosyl trichloroacetimidate. The common glycosyl dipeptide:[beta-D-GlcA-(1 -> 3)-beta-D-Gal-(1 -> 3)-beta-D-Gal-(1 -> 4)-beta-D- Xyl-(1 -> O)-Ser-Gly] was synthesized by glycosylation of the corresponding tetraosyl trichloroacetimidate and Ser-Gly moiety. The glycosyl dipeptide was coupled with other core peptide parts in solution phase and on a solid support. These glycosyl hexapeptides were then transformed into the desired target compounds.