(3aR,4R,6S,6aR)-4-methoxy-2,2-dimethyl-6-styryltetrahydrofuro[3,4-d][1,3]dioxole | 63599-69-9

• 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: (3aR,4R,6S,6aR)-4-methoxy-2,2-dimethyl-6-styryltetrahydrofuro[3,4-d][1,3]dioxole
• 英文别名: (3aR,4R,6R,6aR)-4-methoxy-2,2-dimethyl-6-((E)-styryl)tetrahydrofuro[3,4-d][1,3]dioxole；(3aR,4R,6S,6aR)-4-methoxy-2,2-dimethyl-6-[(E)-2-phenylethenyl]-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxole
• CAS: 63599-69-9
• 化学式: C₁₆H₂₀O₄
• 分子量: 276.332
• InChiKey: JXDFREYEWKGXSP-TUGCRNSMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  甲基-2,3-O-异亚丙基-beta-D-呋喃核糖苷 在 咪唑 、 magnesium bis(monoperoxyphthalate)hexahydrate 、 碘 、 双(三甲基硅烷基)氨基钾 、 potassium carbonate 、 三苯基膦 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 丙酮 为溶剂， 反应 3.33h， 生成 (3aR,4R,6S,6aR)-4-methoxy-2,2-dimethyl-6-styryltetrahydrofuro[3,4-d][1,3]dioxole
  参考文献：
  名称：

  A Carbohydrate-Based Julia–Kocienski Reagent for Syntheses of Chain-Extended and C-Linked Saccharides

  摘要：

  The carbohydrate-derived Julia-Kocienski reagent 2-{[(3aS, 4S, 6R, 6aR)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl]methylsulfonyl}-1,3-benzothiazole (6) was prepared from D-ribose and investigated in the eponymous olefination. The base-promoted generation of the Julia anion induced a rearrangement to the corresponding L-lyxose epimer 2{[( 3aS, 4R, 6R, 6aR)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3] dioxol-4-yl] methylsulfonyl}-1,3-benzothiazole (12), which reacted readily with aldehydes and with a gluconolactone. The latter reaction furnished an exo-glycal-linked C-diglycoside.

  DOI：

  10.1055/s-0033-1340851

文献信息

• Stereospecific Photoredox‐Catalyzed Vinylations to Function­alized Alkenes and C‐Glycosides
  作者：Kumar Bhaskar Pal、Ester Maria Di Tommaso、A. Ken Inge、Berit Olofsson

  DOI：10.1002/anie.202301368

  日期：——

  photo-catalyzed, transition-metal-free C−C cross-coupling reaction has been developed with 4-alkyl-dihydropyridines (DHPs) and vinylbenziodoxol(on)es (VBX, VBO) to synthesize di- and trisubstituted alkenes with complete E : Z selectivity. A diastereoselective C-vinylation of glycosides was also developed. Preliminary mechanistic studies indicate a concerted radical coupling pathway.

  用 4-烷基二氢吡啶 (DHPs) 和乙烯基苯并氧醇 (on)es (VBX, VBO) 开发了一种方便的光催化、无过渡金属的 C−C 交叉偶联反应，以合成具有完整的二和三取代烯烃E : Z选择性。还开发了糖苷的非对映选择性C-乙烯基化。初步的机理研究表明协调一致的自由基偶联途径。
• A Carbohydrate-Based Julia–Kocienski Reagent for Syntheses of Chain-Extended and C-Linked Saccharides
  作者：Horst Kunz、James Bull

  DOI：10.1055/s-0033-1340851

  日期：——

  The carbohydrate-derived Julia-Kocienski reagent 2-[(3aS, 4S, 6R, 6aR)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl]methylsulfonyl}-1,3-benzothiazole (6) was prepared from D-ribose and investigated in the eponymous olefination. The base-promoted generation of the Julia anion induced a rearrangement to the corresponding L-lyxose epimer 2[( 3aS, 4R, 6R, 6aR)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3] dioxol-4-yl] methylsulfonyl}-1,3-benzothiazole (12), which reacted readily with aldehydes and with a gluconolactone. The latter reaction furnished an exo-glycal-linked C-diglycoside.