2-[(2R,5S)-5-((R)-2-Benzyloxy-1-hydroxy-ethyl)-5-methyl-tetrahydro-furan-2-yl]-propan-2-ol | 121693-61-6

• 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: 2-[(2R,5S)-5-((R)-2-Benzyloxy-1-hydroxy-ethyl)-5-methyl-tetrahydro-furan-2-yl]-propan-2-ol
• 英文别名: 2-[(2R,5S)-5-[(1R)-1-hydroxy-2-phenylmethoxyethyl]-5-methyloxolan-2-yl]propan-2-ol
• CAS: 121693-61-6
• 化学式: C₁₇H₂₆O₄
• 分子量: 294.391
• InChiKey: SNIWYLNQUAXUSX-INMHGKMJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-[(2R,5S)-5-((R)-2-Benzyloxy-1-hydroxy-ethyl)-5-methyl-tetrahydro-furan-2-yl]-propan-2-ol 在 palladium on activated charcoal sodium hydroxide 、 9-borabicyclo[3.3.1]nonane dimer 、 草酰氯 、 四溴化碳 、 氢气 、 双氧水 、 sodium hydride 、 二甲基亚砜 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 (S)-2-[(2R,4aR,6R,8aS)-6-((2S,5R)-5-Bromo-2,6,6-trimethyl-tetrahydro-pyran-2-yl)-8a-methyl-octahydro-pyrano[3,2-b]pyran-2-yl]-4-((1S,2R,7R)-1,6,6-trimethyl-3,5,10-trioxa-bicyclo[5.2.1]dec-2-yl)-butan-2-ol
  参考文献：
  名称：

  Total synthesis of venustatriol

  摘要：

  DOI：

  10.1016/0040-4039(88)85113-x
• 作为产物：
  描述：

  (2R,3R)-3-methyl-3-(4-methyl-3-pentenyl)oxiranemethanol 在 高氯酸 、 sodium hydride 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 38.0h， 生成 2-[(2R,5S)-5-((R)-2-Benzyloxy-1-hydroxy-ethyl)-5-methyl-tetrahydro-furan-2-yl]-propan-2-ol
  参考文献：
  名称：

  Total synthesis of venustatriol

  摘要：

  DOI：

  10.1016/0040-4039(88)85113-x

文献信息

• A General Oxidative Cyclization of 1,5-Dienes Using Catalytic Osmium Tetroxide
  作者：Timothy J. Donohoe、Sam Butterworth

  DOI：10.1002/anie.200390253

  日期：2003.2.24
• Total Synthesis of Thyrsiferyl 23-Acetate, a Specific Inhibitor of Protein Phosphatase 2A and an Anti-Leukemic Inducer of Apoptosis
  作者：Isabel C. González、Craig J. Forsyth

  DOI：10.1021/ja000001r

  日期：2000.9.1

  A convergent synthetic entry to the squalenoid polyether system has been developed and applied to the biologically active marine natural products thyrsiferyl 23-acetate (la), thyrsiferol (Ib), thyrsiferyl 18-acetate (Ic), and thyrsiferyl 18,23-diacetate (Id). This involved the separate construction of two advanced intermediates representing the C1-C15 (4) and C16-C24 (5) domains, followed by their organochromium-mediated coupling, installation of the tertiary alcohol at C15, and manipulation of the C18 and C23 acetate moieties. The C1-C15 (4) intermediate containing the three tetrahydropyranyl rings (A-B-C) was derived from two preconstructed tetrahydropyran-containing units representing the functionalized A (C2-C6) and C (C10-C14) rings (6 and 7, respectively). The bromotetrahydropyranyl A ring was obtained via bromoetherification of the hydroxyalkene 16, which was synthesized from (2R,3R)-epoxy geraniol. The C ring was stereoselectively constructed by acid-catalyzed opening of the hydroxy epoxide 32, derived from D-glutamic acid. Intermediates 6 and 7 were-joined using organochromium conditions, and ketone and hydroxyl functionalities were installed at carbons:7 and 11, respectively. Closure of the B ring was accomplished stereoselectively by formation of species derived from a C7, C11 keto-alcohol and in situ reduction of a tetrahydropyranyl oxonium. The complementary tetrahydrofuran D (C19-C22) ring was obtained from a geraniol-derived tertiary hydroxy alkene (44) via a stereoselective Re(VII)-induced syn-oxidative cyclization. The side chain appended to the D ring was elaborated into trans-alkenyl iodide 5 under Takai reaction conditions. CrCl2-mediated coupling of aldehyde 4 containing the secondary bromide at C3 of the natural products, with iodide 5 bearing acetate moieties at C18 and C23, installed the C15-C16 carbon-carbon bond. The resultant C15 allylic carbinol was converted into an cr,P-saturated ketone, and the final methyl group was added stereoselectively using methylmagnesium bromide. Saponification of the C18 acetate yielded la, whereas cleavage of both C18 and C23 acetates gave the triol Ib. This modular entry into the squalenoid-polyether system may facilitate further evaluation of the antileukemic, apoptosis-inducing, protein serine/threonine phosphatase 2A inhibitory and anti-multidrug resistance activities of the thyrsiferol-derived natural products.
• A Lewis Acid Promoted Oxidative Cyclization
  作者：Timothy J. Donohoe、Paul C. M. Winship、Daryl S. Walter

  DOI：10.1021/jo901243y

  日期：2009.8.21

  Replacing trifluoroacetic acid with it catalytic amount of Lewis acid in the osmium mediated oxidative cyclization results in higher yielding reactions that can proceed nearly an order of magnitude faster. The osmium loading can also be reduced to as little its 0.2 mol %. Furthermore, these mildly acidic conditions are capable of tolerating a wide range of acid sensitive protecting groups that are incompatible with previous cyclization conditions.
• COREY, E. J.;HA, DEOK-CHAN, TETRAHEDRON LETT., 29,(1988) N 26, C. 3171-3174
  作者：COREY, E. J.、HA, DEOK-CHAN

  DOI：——

  日期：——
• Total synthesis of venustatriol
  作者：E.J. Corey、Deok-Chan Ha

  DOI：10.1016/0040-4039(88)85113-x

  日期：1988.1