p-tert-butylphenyl 4,6-di-O-benzyl-2,3-dideoxy-α,β-D-erythro-hex-2-enopyranoside | 201232-72-6

• 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: p-tert-butylphenyl 4,6-di-O-benzyl-2,3-dideoxy-α,β-D-erythro-hex-2-enopyranoside
• 英文别名: (2R,3S,6S)-6-(4-tert-butylphenoxy)-3-phenylmethoxy-2-(phenylmethoxymethyl)-3,6-dihydro-2H-pyran
• CAS: 201232-72-6
• 化学式: C₃₀H₃₄O₄
• 分子量: 458.598
• InChiKey: BGFCQGGUZRFWRO-ZGIBFIJWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  34
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  苯基溴化镁 、 p-tert-butylphenyl 4,6-di-O-benzyl-2,3-dideoxy-α,β-D-erythro-hex-2-enopyranoside 在 1,2-双(二苯基膦)乙烷氯化镍 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以50%的产率得到phenyl 4,6-di-O-benzyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside
  参考文献：
  名称：

  钯和镍催化的苯基溴化镁向不饱和碳水化合物中的立体化学

  摘要：

  钯配合物PdCl 2（dppf）和镍配合物NiCl 2（dppe）催化不饱和芳氧基碳水化合物与苯基溴化镁的交叉偶联。镍催化剂导致在端基异构体中心的构型反转，而在钯催化剂的情况下仅发生保留。这种非常不常用的保留可能是由于环氧原子的影响

  DOI：

  10.1016/s0022-328x(98)00679-2
• 作为产物：
  描述：

  在 咪唑 、 sodium hydroxide 、 四丁基氟化铵 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 56.0h， 生成 p-tert-butylphenyl 4,6-di-O-benzyl-2,3-dideoxy-α,β-D-erythro-hex-2-enopyranoside
  参考文献：
  名称：

  Synthesis of α- and β-C-Aryl Δ²-Glycopyranosides from p-tert-Butylphenyl Δ²-Glycopyranosides via Grignard Reagents

  摘要：

  Treatment of p-tert-butylphenyl 4,6-di-O-benzyl-2,3-dideoxy-alpha-D-erythro-hex-2-enopyranoside (1a alpha) or the 4,6-di-O-(tert-butyldimethylsilyl) analogue (1b alpha) with various functionalized arylmagnesium bromides in the presence of a catalytic amount of PdCl2(dppf) at 25 degrees C in THF afforded the corresponding unsaturated C-arylglycosides 2-14 having the ct-configuration in quite good yields. Benzyl-, allyl-, and vinylmagnesium bromides gave also the corresponding unsaturated alpha-C-glycosides 15-18, although in lower yields. When the same reaction was performed in the presence of NiCl2(dppe) as the catalyst at -40 degrees C, only the formation of the corresponding unsaturated C-arylglycosides having the beta-configuration was observed. As expected, reaction of phenylmagnesium bromide with p-tert-butylphenyl 4,6-di-O-benzyl-2,3-dideoxy-beta-D-erythro-hex-2-enopyranoside (1a beta) in the presence of NiCl2(dppe) gave only the unsaturated beta-C-phenylglycoside 2a beta, while palladium-catalyzed reaction led to the preponderant formation of C-phenylglycoside 2a alpha. Reaction of PhMgBr with p-tert-butylphenyl 4-O-benzyl-2,3,6-trideoxy-alpha-L-erythro-hex-2-enopyranoside (20) afforded stereospecifically the unsaturated alpha- and beta-C-phenylglycoside 25 in the presence of PdCl2-(dppf) and NiCl2(dppe), respectively.

  DOI：

  10.1021/jo9714674

文献信息

• FeCl₃/C as an efficient catalyst for Ferrier rearrangement of 3,4,6-tri-<i>O</i>-Benzyl-D-glucal
  作者：Yuling Mei、Youxian Dong、Juan Li、Bo Zhang、Guosheng Sun、Jiafen Zhou、Wenshuai Si、Yiwen Han、Zhenliang Wu、Jianbo Zhang

  DOI：10.1080/07328303.2020.1788575

  日期：2020.7.23

  Abstract FeCl3/C was used as an efficient and convenient promoter for glycosylation through Ferrier-type rearrangement of 3,4,6-tri-O-benzyl-D-glucal, which is a relatively unreactive substrate for this type of reaction. The method was applicable to a wide range of alcohols, especially phenols. A series of 2,3-unsaturated-O-glucosides were prepared efficiently (47–92%) by this method under mild conditions

  摘要FeCl3 / C被用作通过3,4,6-tri-O-苄基-D-葡糖的Ferrier型重排进行糖基化的有效且方便的启动子，它是此类反应的相对反应性底物。该方法适用于多种醇，尤其是酚。通过该方法在温和的条件下，可以有效地制备一系列2，3-不饱和的O-葡萄糖苷（47-92％）。