(5S,6R)-6-(4-Methoxy-benzyloxymethyl)-5-methyl-tetrahydro-pyran-2-one | 585526-22-3

• 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: (5S,6R)-6-(4-Methoxy-benzyloxymethyl)-5-methyl-tetrahydro-pyran-2-one
• 英文别名: (5S,6R)-6-[(4-methoxyphenyl)methoxymethyl]-5-methyloxan-2-one
• CAS: 585526-22-3
• 化学式: C₁₅H₂₀O₄
• 分子量: 264.321
• InChiKey: WXYYTCIINKDRGX-FZMZJTMJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (5S,6R)-6-(4-Methoxy-benzyloxymethyl)-5-methyl-tetrahydro-pyran-2-one 、 tert-butyl-[(2R,3S)-1-[(4-methoxyphenyl)methoxy]-3-methylpent-4-yn-2-yl]oxy-dimethylsilane 在 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 以23%的产率得到(2R,3S,9S,10R)-2-(tert-Butyl-dimethyl-silanyloxy)-10-hydroxy-1,11-bis-(4-methoxy-benzyloxy)-3,9-dimethyl-undec-4-yn-6-one
  参考文献：
  名称：

  Efficient synthesis of the 6,6-spiroacetal of spirofungin A

  摘要：

  The 6,6-spiroacetal segment of spirofungin A, an antifungal antibiotic isolated from Streptomyces violaceusniger Tu 4113, was efficiently prepared via the coupling reaction of the Weinreb amide and the alkyne which are readily available from the common intermediate. The synthesis includes the unsymmetrization through a stereoinversion at the C11 position and the transacetalization as the key steps. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)01184-5
• 作为产物：
  描述：

  (2E)-4-[(4-methoxyphenyl)methoxy]-2-methylbut-2-en-1-ol 在 palladium on activated charcoal titanium(IV) isopropylate 、 叔丁基过氧化氢 、 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 、 甲酸 、 草酰氯 、 L-(+)-酒石酸二乙酯 、 三丁基膦 、 camphor-10-sulfonic acid 、 氢气 、 二甲基亚砜 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 乙酸乙酯 、 三乙胺 、 苯 为溶剂， 反应 2.0h， 生成 (5S,6R)-6-(4-Methoxy-benzyloxymethyl)-5-methyl-tetrahydro-pyran-2-one
  参考文献：
  名称：

  Efficient synthesis of the 6,6-spiroacetal of spirofungin A

  摘要：

  The 6,6-spiroacetal segment of spirofungin A, an antifungal antibiotic isolated from Streptomyces violaceusniger Tu 4113, was efficiently prepared via the coupling reaction of the Weinreb amide and the alkyne which are readily available from the common intermediate. The synthesis includes the unsymmetrization through a stereoinversion at the C11 position and the transacetalization as the key steps. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)01184-5

文献信息

• Efficient synthesis of the 6,6-spiroacetal of spirofungin A
  作者：Takeshi Shimizu、Junichi Kusaka、Haruaki Ishiyama、Tadashi Nakata

  DOI：10.1016/s0040-4039(03)01184-5

  日期：2003.6

  The 6,6-spiroacetal segment of spirofungin A, an antifungal antibiotic isolated from Streptomyces violaceusniger Tu 4113, was efficiently prepared via the coupling reaction of the Weinreb amide and the alkyne which are readily available from the common intermediate. The synthesis includes the unsymmetrization through a stereoinversion at the C11 position and the transacetalization as the key steps. (C) 2003 Elsevier Science Ltd. All rights reserved.