2-deoxy-3-O-<(4-methoxyphenyl)methyl>-4,5-O-(1-methylethylidene)-D-erythro-pentose | 152453-72-0

• 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-deoxy-3-O-<(4-methoxyphenyl)methyl>-4,5-O-(1-methylethylidene)-D-erythro-pentose
• 英文别名: (3S,4'R)-3-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)-3-p-methoxybenzyloxypropanal；(S)-3-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-3-((4-methoxybenzyl)oxy)propanal；(3S)-3-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-[(4-methoxyphenyl)methoxy]propanal
• CAS: 152453-72-0
• 化学式: C₁₆H₂₂O₅
• 分子量: 294.348
• InChiKey: NPNHQRLXNWDKPD-LSDHHAIUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-deoxy-3-O-<(4-methoxyphenyl)methyl>-4,5-O-(1-methylethylidene)-D-erythro-pentose 在 chromium dichloride 、 indium 、 nickel dichloride 咪唑 、 盐酸 、 4-二甲氨基吡啶 、 sodium periodate 、 正丁基锂 、 草酰氯 、 三丁基膦 、 L-Selectride 、 sodium hydride 、 二异丁基氢化铝 、 戴斯-马丁氧化剂 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 吡啶 、 二氯甲烷 、 水 、 二甲基亚砜 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 生成 4-{6-[6,11-bis-(tert-butyl-dimethyl-silanyloxy)-10-(4-methoxy-benzyloxy)-13-(4-methyl-3,6-dihydro-2H-pyran-2-yl)-4-methylene-trideca-7,12-dienyl]-5-methoxy-5,6-dihydro-2H-pyran-2-yl}-but-2-ynoic acid
  参考文献：
  名称：

  Synthesis of 8-(S)-methoxy-11-desmethyl laulimalide: a novel laulimalide analogue

  摘要：

  A strategy is outlined which enables preparation of novel laulimalide analogues at C.8 and C.11. A representative analogue, 8-(S)-methoxy-11-destmethyl laulimalide, was synthesized via this route. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.12.056
• 作为产物：
  描述：

  1-(2,2-dimethyl-[1,3]dioxolan-4-yl)-3,3-bis-ethylsulfanyl-propan-1-ol 在 sodium hydride 、 mercury dichloride 、 mercury(II) oxide 作用下， 以 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 2.67h， 生成 2-deoxy-3-O-<(4-methoxyphenyl)methyl>-4,5-O-(1-methylethylidene)-D-erythro-pentose
  参考文献：
  名称：

  First total synthesis and determination of the absolute configuration of mueggelone

  摘要：

  All the four possible stereoisomers of mueggelone, an inhibitor of fish development, were efficiently synthesized in a stereoselective manner starting from D-arabinose, and the absolute configuration was determined to be 9R, 12S, 13S. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00279-4

文献信息

• First stereo selective synthesis of 5-O-feruloyl-2-deoxy-d-ribono-γ-lactone
  作者：K. Ravi Ganesh、K. Raghavendra Rao、T.V. Pratap、A. Raghunadh、S. Praveen Kumar、M.V. Basaveswara Rao、C. Murthy、Suresh Babu Meruva

  DOI：10.1016/j.tetlet.2016.09.041

  日期：2016.10

  The first stereo selective synthesis of 5-O-feruloyl-2-deoxy-d-ribono-γ-lactone was achieved by coupling reaction of substituted ferulic acid and hydroxy methyl ribono lactone and followed by deprotection of O-PMB. The spectroscopic data were compared with the reported values and a clear indication to the absolute stereochemistry of the natural 5-O-feruloyl-2-deoxy-d-ribono-γ-lactone.

  的第一立体声选择性合成5- ö -feruloyl -2-脱氧d -ribono-γ内酯通过偶合取代的阿魏酸和羟基甲基核糖酸内酯的反应来实现，并随后脱保护Ó -PMB。光谱数据与文献报道值和明确指示到自然的绝对立体化学进行了比较5- ö -feruloyl -2-脱氧d -ribono-γ内酯。
• Total Synthesis of the Macrolide Antitumor Antibiotic Lankacidin C
  作者：Andrew S. Kende、Kun Liu、Istvan Kaldor、Gilbert Dorey、Kevin Koch

  DOI：10.1021/ja00136a025

  日期：1995.8

  The first total synthesis of natural (-)-lankacidin C (I) has been achieved by a convergent, enantioselective sequence starting from D-arabinose and L-aspartic acid, proceeding through the tricyclic carbamate 15 as an advanced relay intermediate. Specifically, the beta-lactam diene intermediate 41 is acylated by the thiopyridyl ester 34c. The resulting beta-ketolactam 42 is stereospecifically reduced by KEt(3)BH to carbinol 43, which on desilylation undergoes acid-catalyzed N --> O acyl migration to yield the delta-lactone 44. The derived iodo aldehyde 46 undergoes Stille coupling to give tetraene 54a, which upon Stork-Takahashi cyclization to ketone 56 and CBS reduction gives the key relay 15. N-acylation of the latter, and then regioselective carbamate scission followed by Dess-Martin oxidation, produces the target antibiotic (-)-lankacidin C (1).
• First total synthesis of mueggelone
  作者：Ken Ishigami、Hajime Motoyoshi、Takeshi Kitahara

  DOI：10.1016/s0040-4039(00)01285-5

  日期：2000.11

  All the four possible stereoisomers of mueggelone, an inhibitor of fish development, were efficiently synthesized in a stereoselective manner starting from D-arabinose, and the absolute configuration was determined to be 9R,12S,13S. (C) 2000 Elsevier Science Ltd. All rights reserved.
• [EN] LAULIMALIDE ANALOGS WITH ANTI-CANCER ACTIVITITY<br/>[FR] ANALOGUES DE LAULIMALIDE ET UTILISATIONS DE CEUX-CI
  申请人：EISAI CO LTD

  公开号：WO2005030779A3

  公开（公告）日：2008-01-24
• Synthesis and biological evaluation of (−)-laulimalide analogues
  作者：Brian M. Gallagher、Francis G. Fang、Charles W. Johannes、Marc Pesant、Martin R. Tremblay、Hongjuan Zhao、Kozo Akasaka、Xiang-yi Li、Junke Liu、Bruce A. Littlefield

  DOI：10.1016/j.bmcl.2003.12.001

  日期：2004.2

  Analogues of the marine natural product (-)-laulimalide were prepared by total synthesis and evaluated in vitro for anticancer activity.