(+)-[(2R,3S,6S)-2-(benzoyloxymethyl)-6-methoxyoxan-3-yl] benzoate | 145593-73-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (+)-[(2R,3S,6S)-2-(benzoyloxymethyl)-6-methoxyoxan-3-yl] benzoate
• 英文别名: [(2R,3S,6S)-3-benzoyloxy-6-methoxyoxan-2-yl]methyl benzoate
• CAS: 145593-73-3
• 化学式: C₂₁H₂₂O₆
• 分子量: 370.402
• InChiKey: JYUYXPZLHAXSES-OTWHNJEPSA-N

物化性质

• 沸点：
  492.0±45.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (+)-[(2R,3S,6S)-2-(benzoyloxymethyl)-6-methoxyoxan-3-yl] benzoate 在 N,O-双三甲硅基乙酰胺 、 三氟甲磺酸三甲基硅酯 、 氨 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 46.0h， 生成 9-(2',3'-Dideoxy-β-D-glucopyranosyl)hypoxanthin
  参考文献：
  名称：

  Warum Pentose- and nichtHexose-Nucleinsäuren??。Teil V.（Purin-Purin）-Basenpaarung在同源DNS-Reihe中：鸟嘌呤，异鸟嘌呤，2,6-二氨基嘌呤和黄嘌呤†

  摘要：

  为什么是戊糖而不是己糖核酸？同源DNA中的嘌呤-嘌呤配对：鸟嘌呤，异鸟嘌呤，2,6-二氨基嘌呤和黄嘌呤

  DOI：

  10.1002/hlca.19980810302
• 作为产物：
  描述：

  4,6-O-benzylidene-1-O-methyl-α-D-glucopyranoside 在 镍 咪唑 、 sodium hydroxide 、 N-溴代丁二酰亚胺(NBS) 、 碘仿 、 偶氮二异丁腈 、 氢气 、 三苯基膦 、 barium carbonate 作用下， 以 甲醇 、 四氯化碳 、 水 、 甲苯 为溶剂， 40.0 ℃ 、530.0 kPa 条件下， 反应 26.25h， 生成 (+)-[(2R,3S,6S)-2-(benzoyloxymethyl)-6-methoxyoxan-3-yl] benzoate
  参考文献：
  名称：

  Synthesis and opioid-receptor binding of novel amino-substituted morphan analogues

  摘要：

  Starting with methyl 4,6-O-benzylidene-alpha -D-glucopyranoside (4), an optimized procedure is reported for preparation of the bromide 7, which is transformed into the N-acylated heptopyranosamine 9. After introduction of an axially positioned azido moiety in position 3 intramolecular N/O-acetal formation succeeds to provide the morphan analogue 17. In receptor binding studies with radioligands the amines 18b-18d reveal higher affinity for mu -receptors than for kappa -receptors. The most mu -active compound 18b (K-i = 14 nM) contains two aryl substituents, which presumably may occupy both aryl binding sites of mu -receptors.

  DOI：

  10.1002/1521-4184(200109)334:8/9<284::aid-ardp284>3.0.co;2-b

文献信息

• Warum Pentose- und nicht Hexose-Nucleinsäuren??. Teil II. Oligonucleotide aus 2′,3′-Dideoxy-β-<scp>D</scp>-glucopyranosyl-Bausteinen (‘Homo-DNS’): Herstellung.
  作者：Markus Böhringer、Hans-JÖRg Roth、Jürg Hunziker、Michael Göbel、Ravichandran Krishnan、Alfred Giger、Bernd Schweizer、Jakob Schreiber、Christian Leumann、Albert Eschenmoser

  DOI：10.1002/hlca.19920750503

  日期：1992.8.13

  Why Pentose and Not Hexose Nucleic Acids? Part II. Preparation of Oligonucleotides Containing 2′,3′-Dideoxy-β-D-glucopyranosyl Building Blocks(7)

  为什么是戊糖而不是己糖核酸？第二部分。包含2'，3'-双脱氧-β-D-吡喃葡萄糖基结构单元的寡核苷酸的制备（7）
• Synthesis of hexopyranosyl acetates and 2,3-disubstituted tetrahydropyrans via chemoselective hydrogenation of hex-2-enopyranosyl acetates
  作者：Kaname Sasaki、Takayuki Wakamatsu、Shuichi Matsumura、Kazunobu Toshima

  DOI：10.1016/j.tetlet.2006.09.091

  日期：2006.11

  A simple and easy method for chemoselective synthesis of hexopyranosyl acetates and 2,3-disubstituted tetrahydropyrans from hex-2-enopyranosyl acetates was demonstrated. The former was achieved by hydrogenation catalyzed by Rh/Al2O3 in EtOAc/toluene solvent at 0 °C, while the latter was carried out using Pd/C in EtOH/AcOH at 25 °C.

  展示了一种简单易行的方法，用于从乙酸-2-烯并吡喃糖基乙酸酯化学选择性合成乙酸己吡喃酯基乙酸酯和2,3-二取代的四氢吡喃。前者是通过Rh / Al 2 O 3在EtOAc /甲苯溶剂中于0°C催化氢化而实现的，而后者是通过Pd / C在25°C的EtOH / AcOH中进行的。
• Diastereoselective Synthesis of 2′,3′-Dideoxy- β-<i>C</i>- Glucopyranosides as Intermediates for the Synthesis of 2′,3′-Dideoxy-β-D-Glucopyranosyl-<i>C</i>-Nucleosides
  作者：Michael Löpfe、Jay S. Siegel

  DOI：10.1080/15257770701508695

  日期：2007.11.26

  An extension of the Vorbruggen method of nucleotide synthesis for the synthesis of G glucopyranosides, as intermediates for C-nucleosides, is described. It could be shown that the diastereoselectivity of the reaction can be tuned by a simple change of protecting groups.
• Synthesis and opioid-receptor binding of novel amino-substituted morphan analogues
  作者：Georg Höfner、Benedikt Streicher、Bernhard Wünsch

  DOI：10.1002/1521-4184(200109)334:8/9<284::aid-ardp284>3.0.co;2-b

  日期：2001.9

  Starting with methyl 4,6-O-benzylidene-alpha -D-glucopyranoside (4), an optimized procedure is reported for preparation of the bromide 7, which is transformed into the N-acylated heptopyranosamine 9. After introduction of an axially positioned azido moiety in position 3 intramolecular N/O-acetal formation succeeds to provide the morphan analogue 17. In receptor binding studies with radioligands the amines 18b-18d reveal higher affinity for mu -receptors than for kappa -receptors. The most mu -active compound 18b (K-i = 14 nM) contains two aryl substituents, which presumably may occupy both aryl binding sites of mu -receptors.
• Warum Pentose- und nicht Hexose-Nucleins�uren??. Teil V. (Purin-Purin)-Basenpaarung in der homo-DNS-Reihe: Guanin, Isoguanin, 2,6-Diaminopurin und Xanthin
  作者：Katrin Groebke、J�rg Hunziker、William Fraser、Ling Peng、Ulf Diederichsen、Kaspar Zimmermann、Armin Holzner、Christian Leumann、Albert Eschenmoser

  DOI：10.1002/hlca.19980810302

  日期：——

  Why Pentose- and Not Hexose-Nucleic Acids? Purine-Purine Pairing in homo-DNA: Guanine,Isoguanine, 2,6-Diaminopurine, and Xanthine

  为什么是戊糖而不是己糖核酸？同源DNA中的嘌呤-嘌呤配对：鸟嘌呤，异鸟嘌呤，2,6-二氨基嘌呤和黄嘌呤