(2R,3R,4R)-4-(tert-butyldimethylsilyloxy)-3-(p-methoxybenzyloxy)-2-vinyl-2,3-dihydro-2H-pyran | 916154-05-7

• 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,3R,4R)-4-(tert-butyldimethylsilyloxy)-3-(p-methoxybenzyloxy)-2-vinyl-2,3-dihydro-2H-pyran
• 英文别名: (2R,3R,4R)-3-O-(4-methoxybenzyl)-4-O-tert-butyldimethylsilyl-2-vinyl-2,3-dihydro-2H-pyran；(2R,3R,4R)-4-(tert-butyldimethylsilyloxy)-3-(4-methoxybenzyloxy)-2-vinyl-3,4-dihydro-2H-pyran；tert-butyl-[[(2R,3R,4R)-2-ethenyl-3-[(4-methoxyphenyl)methoxy]-3,4-dihydro-2H-pyran-4-yl]oxy]-dimethylsilane
• CAS: 916154-05-7
• 化学式: C₂₁H₃₂O₄Si
• 分子量: 376.568
• InChiKey: WWHVKRPGRYDQQK-VAMGGRTRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.07
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.52
• 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：

  (2R,3R,4R)-4-(tert-butyldimethylsilyloxy)-3-(p-methoxybenzyloxy)-2-vinyl-2,3-dihydro-2H-pyran 在 吡啶 、 4-二甲氨基吡啶 、 lithium hydroxide 、 三氟甲磺酸三甲基硅酯 、 四丁基氟化铵 、 silica gel 、 三乙胺 、 pyridinium chlorochromate 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 52.5h， 生成 (S)-hept-6-en-2-yl (3R,4S,5S)-3-benzoyloxy-5-benzyloxy-4-hydroxyhept-6-enoate
  参考文献：
  名称：

  The First Total Synthesis of Sporiolide A

  摘要：

  The first total synthesis of the natural cytotoxic agent sporiolide A has been accomplished from D-glucal in 16 steps with 6.1% overall yield. Carbohydrates were applied as the chiral templates to manipulate the absolute configuration during the synthesis. Pyridinium chlorochromate (PCC)-promoted transformation of the cyclic enol-ether to lactone, followed by Yamaguchi esterification and intramolecular ring closure metathesis, greatly facilitates synthesis of the target compound.

  DOI：

  10.1021/jo0615504
• 作为产物：
  描述：

  3,6-双邻(叔丁基二甲基甲硅烷基)-D-葡萄烯糖 在 吡啶 、 草酰氯 、 氢氟酸 、 sodium hydride 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.5h， 生成 (2R,3R,4R)-4-(tert-butyldimethylsilyloxy)-3-(p-methoxybenzyloxy)-2-vinyl-2,3-dihydro-2H-pyran
  参考文献：
  名称：

  The First Total Synthesis of Sporiolide A

  摘要：

  The first total synthesis of the natural cytotoxic agent sporiolide A has been accomplished from D-glucal in 16 steps with 6.1% overall yield. Carbohydrates were applied as the chiral templates to manipulate the absolute configuration during the synthesis. Pyridinium chlorochromate (PCC)-promoted transformation of the cyclic enol-ether to lactone, followed by Yamaguchi esterification and intramolecular ring closure metathesis, greatly facilitates synthesis of the target compound.

  DOI：

  10.1021/jo0615504

文献信息

• [EN] METHOD OF FORMING OSELTAMIVIR AND DERIVATIVES THEREOF<br/>[FR] PROCÉDÉ DE FORMATION D'OSELTAMIVIR ET DE SES DÉRIVÉS ET APPLICATIONS CORRESPONDANTES
  申请人：UNIV NANYANG

  公开号：WO2009078813A1

  公开（公告）日：2009-06-25

  A process is provided for the synthesis of 4,5-diamino cyclohexene carboxylate ester (1): or a pharmaceutically acceptable salt thereof. R1 - R3 are a silyl-, an aliphatic, alicyclic, aromatic, arylaliphatic, or an arylalicyclic group. R4, R11 and R12 are H, a silyl-group, an aliphatic, alicyclic, aromatic, arylaliphatic, or an arylalicyclic group. 3,4-Dihydropyran compound (9): with R5 and R6 being suitable protecting groups, is reacted to form aldehyde (4): which is oxidized and converted to N-substituted carbamate (3): with R7 being a suitable protecting group. (3) is, via oxazolinidone (13): converted to azido carboxylate ester (2): and then to 4,5-diamino cyclohexene carboxylate ester (1).

  提供了一种用于合成4,5-二氨基环己烯羧酸酯（1）或其药用可接受的盐的过程。R1 - R3是硅基、脂肪、脂环、芳香、芳脂或芳环基团。R4、R11和R12是H、硅基、脂肪、脂环、芳香、芳脂或芳环基团。将3,4-二氢吡喃化合物（9）与适当的保护基R5和R6反应，形成醛（4），氧化并转化为N-取代的碳酸酯（3），其中R7是适当的保护基。通过噁唑啉二酮（13）将（3）转化为偶氮羧酸酯（2），然后转化为4,5-二氨基环己烯羧酸酯（1）。
• Sugar-Based Synthesis of Tamiflu and Its Inhibitory Effects on Cell Secretion
  作者：Jimei Ma、Yanying Zhao、Simon Ng、Jing Zhang、Jing Zeng、Aung Than、Peng Chen、Xue-Wei Liu

  DOI：10.1002/chem.200902048

  日期：2010.4.19

  influenza, but the insufficient supply and side‐effects of this drug demand urgent solutions. We present a practical synthesis of Tamiflu by using novel synthetic routes, cheap reagents, and the abundantly available starting material D‐glucal. The strategy features a Claisen rearrangement of hexose to obtain the cyclohexene backbone and introduction of diamino groups through tandem intramolecular aziridination

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• An Orthogonally Protected Cyclitol for the Construction of Nigerose- and Dextran-Mimetic Cyclophellitols
  作者：Tim P. Ofman、Florian Küllmer、Gijsbert A. van der Marel、Jeroen D. C. Codée、Herman S. Overkleeft

  DOI：10.1021/acs.orglett.1c03723

  日期：2021.12.17

  of exo- and endoglycosidases. Efficient synthetic methodologies are needed to fully capitalize on this intriguing class of mechanism-based enzyme deactivators. We report the synthesis of an orthogonally protected cyclitol from d-glucal (19% yield over 12 steps) and its use in the synthesis of α-(1,3)-linked di- and trisaccharide dextran mimetics. These new glycomimetics may find use as Dextranase inhibitors

  Cyclophellitols 是外切和内切糖苷酶的有效抑制剂。需要有效的合成方法来充分利用这一类有趣的基于机制的酶失活剂。我们报告了从d-葡聚糖合成正交保护的环醇（12 步产率为 19%）及其在 α-(1,3)-连接的二糖和三糖葡聚糖模拟物的合成中的用途。这些新的糖类模拟物可用作葡聚糖酶抑制剂，而开发的化学物质可用于扩大糖加工酶靶向糖类模拟物的范围。
• Synthesis of sporiolide B from d-glucal
  作者：Qi Chen、Yuguo Du

  DOI：10.1016/j.carres.2007.04.013

  日期：2007.8

  A total synthesis of the 12-membered ring natural macrolide, sporiolide B, was achieved from D-glucal in 17 steps with 4.8% overall yield. The required stereochemical configuration at C-3 and C-5 in sporiolide B was easily introduced by applying a Mitsunobu reaction on the chiral template D-glucal. Yamaguchi esterification and ring closing metathesis greatly improved the access to the target compound. (c) 2007 Elsevier Ltd. All rights reserved.