p-tert-butylphenyl 4,6-di-O-benzyl-2,3-dideoxy-α,β-D-erythro-hex-2-enopyranoside | 170156-80-6

• 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,6R)-6-(4-tert-butylphenoxy)-3-phenylmethoxy-2-(phenylmethoxymethyl)-3,6-dihydro-2H-pyran
• CAS: 170156-80-6
• 化学式: C₃₀H₃₄O₄
• 分子量: 458.598
• InChiKey: BGFCQGGUZRFWRO-NHKHRBQYSA-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：

  p-tert-butylphenyl 4,6-di-O-benzyl-2,3-dideoxy-α,β-D-erythro-hex-2-enopyranoside 在 tris(dibenzylideneacetone)dipalladium (0) 盐酸 、 苯磺酰胺 、 sodium hydroxide 、 potassium acetate 、 1,4-双(二苯基膦)丁烷 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 为溶剂， 反应 3.0h， 生成 2-(4,6-di-O-benzyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl)2(R,S)-glycine
  参考文献：
  名称：

  SYNTHESIS OF UNSATURATEDC-GLYCOSYL GLYCINES

  摘要：

  Palladium(0)-catalyzed alkylation of 2,3-unsaturated aryl glycoside with ethyl nitroacetace or N-(dipheuylmethylene)glycine ethyl ester in the presence of N,O-bis(trimethylsilyl)acetamide/KOAc afforded ethyl 2-(4,5-di-O-benzyl-2,3-dideoxy-alpha -D-erythro-hex-2-enopyranosyl)-2(R,S)-nitroacetate (2) and ethyl 3-(4,6-di-O-benzyl-2,3-dideoxy-alpha -D-erythro-hex-2-enopyranosyl)-2(R,S)-[(N-diphenylmethylene)amino)]acetate (7), respectively. Hydrogenation of compound 2 afforded the saturated aminoesters, while compound 7 was readily transformed into 2-(4,6-di-O-benzyl-2,3-dideoxy-alpha -D-erythro-hex-2-enopyranosyl)-2(R,S)-glycine (10) by acidic hydrolysis followedby saponification.

  DOI：

  10.1081/car-100103957
• 作为产物：
  描述：

  乙酰化葡萄烯糖 在 sodium hydroxide 、 sodium methylate 作用下， 以 甲醇 、 氯苯 、 甲苯 为溶剂， 反应 44.0h， 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：

  An Easy and Efficient Preparation of Aryl α-O-Δ²−Glycosides

  摘要：

  Ferrier reaction between acetylglycals and p-NO2, m-NO2 and p-t-butylphenol after recrystallization gave aryl O-Delta(2)-glycosides as the pure a anomers. Deacetylation of these compounds and benzylation of the crude diol led to the corresponding aryl alpha-O-Delta(2)-4,6-di-O-benzylglycosides in large amounts.

  DOI：

  10.1080/00397919508011424

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％）。
• Stereospecific synthesis of α- and β-C-aryl-Δ²-glycopyranosides from p-tert-butylphenyl α-O-Δ²-glycopyranoside via Grignard reagents
  作者：Christophe Moineau、Véronique Bolitt、Denis Sinou

  DOI：10.1039/c39950001103

  日期：——

  Palladium-catalysed coupling of p-tert-butylphenyl α-O-Δ2-glycopyranoside with various substituted arylmagnesium bromides provides the corresponding C-α-aryl-Δ2-glycopyranosides, while nickel-mediated reaction allows the preparation of the C-β-aryl anomers.

  钯催化的对叔丁基苯基α-O-Δ2-糖吡喃苷与各种取代的芳基溴化镁反应，生成相应的C-α-芳基-Δ2-糖吡喃苷，而镍介导的反应则允许C-β-芳基异构体的制备。
• Stereochemistry in palladium- and nickel-catalyzed addition of phenylmagnesium bromide to unsaturated carbohydrates
  作者：Christophe Moineau、Véronique Bolitt、Denis Sinou

  DOI：10.1016/s0022-328x(98)00679-2

  日期：1998.9

  Palladium complex PdCl2(dppf) and nickel complex NiCl2(dppe) catalyze cross-coupling of unsaturated aryloxy carbohydrates with phenylmagnesium bromide. The nickel catalyst leads to inversion of configuration at the anomeric center while only retention occurs in the case of the palladium catalyst. This quite unusal retention is probably due to the influence of the ring oxygen atom

  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
• Synthesis of α- and β-<i>C</i>-Aryl Δ²-Glycopyranosides from <i>p</i>-<i>tert</i>-Butylphenyl Δ²-Glycopyranosides via Grignard Reagents
  作者：Christophe Moineau、Véronique Bolitt、Denis Sinou

  DOI：10.1021/jo9714674

  日期：1998.2.1

  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.