4'-methoxyphenyl 4,6-di-O-acetyl-1,2,3-trideoxy-1-C-β-D-erythro-hex-2-enopyranoside | 121518-16-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4'-methoxyphenyl 4,6-di-O-acetyl-1,2,3-trideoxy-1-C-β-D-erythro-hex-2-enopyranoside
• 英文别名: 1'-(4,6-di-O-acetyl-2,3-dideoxy-β-D-erythro-hex-2-enopyranosyl)-4'-methoxybenzene；[(2R,3S,6R)-3-acetyloxy-6-(4-methoxyphenyl)-3,6-dihydro-2H-pyran-2-yl]methyl acetate
• CAS: 121518-16-9
• 化学式: C₁₇H₂₀O₆
• 分子量: 320.342
• InChiKey: GYYIJMCRPIUUPG-IXDOHACOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  苯甲醚 、 乙酰化葡萄烯糖 在 四氯化锡 作用下， 以 1,2-二氯乙烷 为溶剂， 生成 4'-methoxyphenyl 4,6-di-O-acetyl-1,2,3-trideoxy-1-C-β-D-erythro-hex-2-enopyranoside
  参考文献：
  名称：

  2,3-不饱和-吡喃葡萄糖苷：端基构型分配指南

  摘要：

  与先前的报道相反，通过苯甲醚（2）的SnCl 4促进的三-O-乙酰基-D-葡萄糖（1）芳基化反应生成了1'-（4,6-二-O-乙酰基-2） ，3-二脱氧-β-D-赤-己基-2-烯吡喃糖基）-4′-甲氧基苯（3）而不是α-端基异构体（4）。提出了正确分配2,3-不饱和-吡喃葡萄糖苷端基异构体构型的指南，这违反了哈德森等旋定律。

  DOI：

  10.1016/s0040-4039(00)80810-2

文献信息

• Molybdenum-Catalyzed Allylic Substitution in Glycals: A C-C Bond-Forming Ferrier-Type Reaction
  作者：Andrei V. Malkov、Benjamin P. Farn、Nigel Hussain、Pavel Kočovský

  DOI：10.1135/cccc20011735

  日期：——

  The mild, Lewis-acidic complexes [Mo(CO)₄Br₂]₂, (MeCN)₂Mo(CO)₃(SnCl₃)Cl, and (acac)₂Mo(OTf)₂ have been found to catalyze the C(1)-specific C-glycosylation reaction of glycal acetates 1-3 with silyl enol ethers 4a-4c and electron-rich aromatics 5a, 5b (PhOMe, PhOH). While silyl enol ethers produce predominantly α-C-glycopyranosides (with 2 : 1 to 4 : 1 selectivity), aromatics tend to afford mainly β-C-glycopyranosides (2 : 1 to 3 : 1) in a thermodynamically controlled process.

  轻度的、Lewis酸性的配合物[Mo(CO)₄Br₂]₂，(MeCN)₂Mo(CO)₃(SnCl₃)Cl和(acac)₂Mo(OTf)₂被发现能催化糖醇醋酸酯1-3与硅烯醇醚4a-4c以及富电子芳香化合物5a，5b（PhOMe，PhOH）之间的C(1)特异性糖基化反应。虽然硅烯醇醚主要生成α-C-糖基吡喃苷（2：1至4：1的选择性），但芳香化合物倾向于主要产生β-C-糖基吡喃苷（2：1至3：1）在一个热力学控制的过程中。
• Phenolic ferrier reaction and its application to the natural product synthesis
  作者：Toshiro Noshita、Takeyoshi Sugiyama、Yoshiharu Kitazumi、Takayuki Oritani

  DOI：10.1016/0040-4039(94)88297-5

  日期：1994.10

  Aryl O-Δ2-glycosides were synthesized by Ferrier reaction. p-Methoxyphenyl group was oxidatively removed with Ag(DPAH)2.

  芳ø -Δ 2 -glycosides通过Ferrier的反应合成。用Ag（DPAH）2氧化除去对甲氧基苯基。
• Synthesis of C-aryl-Δ2,3-glycopyranosides via uncatalyzed addition of triarylindium reagents to glycals
  作者：Sarah Price、Stephen Edwards、Tiffany Wu、Thomas Minehan

  DOI：10.1016/j.tetlet.2004.05.046

  日期：2004.6

  2,3-Unsaturated-C-aryl glycopyranosides are important intermediates in the synthesis of medicinally important C-aryl glycosides. Treatment of glycal acetates with triarylindiums in ether at room temperature gives good yields of C-aryl-Delta(2,3)-glycosides of predominantly alpha-configuration. The mechanism of this reaction likely involves the formation of an oxocarbenium ion intermediate via indium(III) Lewis acid-assisted ionization of the glycal C.3 acetate. Coupling of trivinyl- and tris(alkynyl)indiums with glycals similarly led to C-vinyl- and Galkynyl-Delta(2,3)-glycosides in good yield. (C) 2004 Elsevier Ltd. All rights reserved.
• Noshita, Toshiro; Sugiyama, Takeyoshi; Kitazumi, Yoshiharu, Bioscience, Biotechnology and Biochemistry, 1995, vol. 59, # 11, p. 2052 - 2055
  作者：Noshita, Toshiro、Sugiyama, Takeyoshi、Kitazumi, Yoshiharu、Oritani, Takayuki

  DOI：——

  日期：——
• CASIRAGHI, GIOVANNI;CORNIA, MARA;COLOMBO, LINO;RASSU, GLORIA;FAVA, GIOVAN+, TETRAHEDRON LETT., 23,(1988) N 43, C. 5549-5552
  作者：CASIRAGHI, GIOVANNI、CORNIA, MARA、COLOMBO, LINO、RASSU, GLORIA、FAVA, GIOVAN+

  DOI：——

  日期：——