(S)-5-benzyloxymethyl-2(5H)-furanone | 72605-53-9

• 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: (S)-5-benzyloxymethyl-2(5H)-furanone
• 英文别名: (2S)-2-(phenylmethoxymethyl)-2H-furan-5-one
• CAS: 72605-53-9
• 化学式: C₁₂H₁₂O₃
• 分子量: 204.225
• InChiKey: HTSRAUGLDNWFOF-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-5-benzyloxymethyl-2(5H)-furanone 在 5% Pd on active carbon 、 palladium dichloride 氢气 作用下， 以 乙醇 为溶剂， 生成 (5S)-5-(hydroxymethyl)-2-oxo-tetrahydrofuran
  参考文献：
  名称：

  天然（-）-和非天然（+）-甜菊糖素的不对称全合成：天然抗肿瘤甜菊糖素的绝对构型的测定

  摘要：

  通过使用丁烯内酯（12）作为共轭1,4-加成的手性受体，证明了合成2,3-二取代的丁-4-醇（10）时几乎完全不对称。完成了天然（-）-和非天然（+）-甜菊糖的高效不对称全合成。天然抗肿瘤甜菜碱的绝对立体结构被确定为1。

  DOI：

  10.1016/s0040-4020(01)82416-9
• 作为产物：
  描述：

  左旋葡萄糖酮 在 三氟甲磺酸 、 双氧水 作用下， 以 二氯甲烷 、 环己烷 、 水 为溶剂， 反应 14.0h， 生成 (S)-5-benzyloxymethyl-2(5H)-furanone
  参考文献：
  名称：

  High-Yielding Diastereoselective syn -Dihydroxylation of Protected HBO: An Access to D-(+)-Ribono-1,4-lactone and 5-O -Protected Analogues

  摘要：

  A diastereoselective chemoenzymatic synthetic pathway to D‐(+)‐ribono‐1,4‐lactone, a versatile chiral sugar derivative widely used for the synthesis of various natural products, has been designed from cellulose‐based levoglucosenone (LGO). This route involves a sustainable Baeyer‐Villiger oxidation of LGO to produce enantiopure (S)‐γ‐hydroxymethyl‐α,β‐butenolide (HBO) that is further functionalized with various protecting groups to provide 5‐O‐protected γ‐hydroxymethyl‐α,β‐butenolides. The latter then undergo a diastereoselective and high‐yielding syn‐dihydroxylation of the α,β‐unsaturated lactone moiety followed by a deprotection step to give D‐(+)‐ribono‐1,4‐lactone. Through this 4‐step synthetic route from LGO, D‐(+)‐ribono‐1,4‐lactone is obtained with d.r. varying from 82:18 to 97:3 and in overall yields between 32 and 41 % depending on the protecting group used. Moreover, valuable synthetic intermediates 5‐O‐tert‐butyldimethylsilyl‐, 5‐O‐tert‐butyldiphenylsilyl‐ as well as 5‐O‐benzyl‐ribono‐1,4‐lactones are obtained in 3 steps from LGO in 58, 61 and 40 %, respectively.

  DOI：

  10.1002/ejoc.201801780

文献信息

• Studies on structurally simple α,β-butenolides—II
  作者：P. Camps、J. Cardellach、J. Font、R.M. Ortuño、O. Ponsati

  DOI：10.1016/0040-4020(82)87017-8

  日期：1982.1

  A short synthesis of the title compound, 16, from d-ribonolactone is described. Two alternative approaches differing in the timing of the CC double bond creation are used to prepare some chiral derivatives of 16. (−)-Ranunculin, a glycoside present in Ranunculaceae, has been synthesized for the first time.

  描述了由d-核糖内酯简短合成标题化合物16。在C alternativeC双键产生时间上有两种不同的替代方法，用于制备一些16的手性衍生物。（ - ） - Ranunculin，糖苷存在于毛茛科，已合成的第一次。
• Modular synthesis of optically active lactones by Ru-catalyzed asymmetric allylic carboxylation and ring-closing metathesis reaction
  作者：Koichiro Takii、Naoya Kanbayashi、Kiyotaka Onitsuka

  DOI：10.1039/c2cc18137a

  日期：——

  A new synthetic route to optically active unsaturated gamma- and delta-lactones has been demonstrated via asymmetric allylic carboxylation with a planar-chiral Cp'Ru catalyst and ring-closing metathesis reaction with a Grubbs II catalyst, and successfully applied to the enantioselective synthesis of (R)-(-)-massoialactone.

  通过使用平面手性Cp'Ru催化剂进行不对称烯丙基羧化和使用Grubbs II催化剂进行闭环复分解反应，已证明了一种新的合成光学活性不饱和γ-和δ-内酯的途径，并将其成功用于对映体的对映体合成（R）-（-）-马来酸内酯。
• Stereoselective Photochemical 1,3-Dioxolane Addition to <i>5-</i>Alkoxymethyl-2(5<i>H</i>)-furanone:  Synthesis of Bis-tetrahydrofuranyl Ligand for HIV Protease Inhibitor UIC-94017 (TMC-114)
  作者：Arun K. Ghosh、Sofiya Leshchenko、Marcus Noetzel

  DOI：10.1021/jo049156y

  日期：2004.11.1

  A convenient synthesis of (3R,3aS,6aR)-3-hydroxyhexahydrofuro[2,3-b]furan, a high-affinity nonpeptidal ligand for HIV protease inhibitor UIC-94017, is described. This inhibitor is undergoing advanced clinical trials. The synthesis utilizes a novel stereoselective photochemical 1,3-dioxolane addition to 5(S)-benzyloxymethyl-2(5H)-furanone as the key step. The requisite furanone derivative was prepared

  描述了一种方便合成的（3 R，3a S，6a R）-3-羟基六氢呋喃[2,3- b ]呋喃，这是一种针对HIV蛋白酶抑制剂UIC-94017的高亲和力非肽配体。该抑制剂正在接受先进的临床试验。合成过程中，除了5（S）-苄氧基甲基-2（5 H）-呋喃酮外，还利用了新型的立体选择性光化学1,3-二氧戊环。通过固定的脂肪酶催化的（±）-1-（苄氧基）-3-丁烯-2-醇的固定化酰化反应和用Grubbs的催化剂进行的闭环烯烃复分解反应，以高对映体过量的形式制备必需的呋喃酮衍生物。将光学活性的双-THF转化为蛋白酶抑制剂2（UIC-94017）。
• Synthesis of Optically Active 4-Benzyloxymethyl- and 4-(4-Methoxyphenoxy)methylbuten-2-olides via Lipase-Mediated Resolution
  作者：Seiichi Takano、Masaki Setoh、Osamu Yamada、Kunio Ogasawara

  DOI：10.1055/s-1993-26037

  日期：——

  A new preparation of optically active 4-benzyloxymethyl- and 4-(4-methoxyphenoxy)methylbuten-2-olides has been developed by employing lipase-mediated resolution and palladium-mediated carbomethoxylation as key steps.

  一种新的光学活性4-苯基氧甲基-和4-(4-甲氧基苯氧)甲基丁烯-2-内酯的制备方法已经被开发，该方法采用了脂肪酶介导的拆分和钯介导的碳甲氧基化作为关键步骤。
• Synthesis of the enantiomers of umbelactone
  作者：Rosa M. Ortuño、Joaquim Bigorra、Josep Font

  DOI：10.1016/s0040-4020(01)86802-2

  日期：1987.1

  Both (+)- and (-)-umbelactone have been synthetized from (R)-γ-hydroxymethyl-γ-butyrolactone and D-ribonolactone, respectively. The absolute configuration of the natural product has shown to beR-(+).

  （+）-和（-）-泛内酯都分别由（R）-γ-羟甲基-γ-丁内酯和D-核糖内酯合成。天然产物的绝对构型显示为R-（+）。