(2S)-2-[(2R,3S,4R,5R)-3,4-dihydroxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]-2-(phenylmethoxycarbonylamino)acetic acid | 127559-13-1

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 5'-脱氧核糖核苷
• 英文名称: (2S)-2-[(2R,3S,4R,5R)-3,4-dihydroxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]-2-(phenylmethoxycarbonylamino)acetic acid
• CAS: 127559-13-1
• 化学式: C₁₉H₂₁N₃O₉
• 分子量: 435.39
• InChiKey: DEHYFJMUKJEBMY-ZHMBSYLPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.16
• 重原子数：
  31.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  180.18
• 氢给体数：
  5.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  (2S)-2-[(2R,3S,4R,5R)-3,4-dihydroxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]-2-(phenylmethoxycarbonylamino)acetic acid 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 6.0h， 生成 Thymine polyoxin C
  参考文献：
  名称：

  Stereoselective synthesis of thymine polyoxin C using an allylic trifluoroacetimidate–trifluoroacetamide rearrangement

  摘要：

  本文描述了胸腺嘧啶多氧素C 3的手性选择性合成方法，其中关键步骤是三氟乙酰亚胺12的[3,3]σ迁移重排转变为三氟乙酰胺13。通过保护基团的交换、臭氧分解和进一步氧化，得到了甲酯20，随后通过引入嘧啶并最终脱保护，将其转化为胸腺嘧啶多氧素C 3。

  DOI：

  10.1039/a905771d
• 作为产物：
  描述：

  ethyl (2R)-2-[(3aR,4R,6S,6aR)-4-methoxy-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]-2-(trifluoromethylsulfonyloxy)acetate 在 palladium dihydroxide 盐酸 、 lithium hydroxide 、 sodium azide 、 三氟甲磺酸三甲基硅酯 、 Dowex 50 WH⁽¹⁺⁾ 、 硫酸 、 氢气 、 碳酸氢钠 、 溶剂黄146 作用下， 以 1,4-二氧六环 、 吡啶 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 (2S)-2-[(2R,3S,4R,5R)-3,4-dihydroxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]-2-(phenylmethoxycarbonylamino)acetic acid
  参考文献：
  名称：

  A Short Path Synthesis of a-Hydroxy Ester from Aldehyde Using (1-Ethoxy-vinyl)lithium and Its Application to the Syntheses of Thymine Polyoxin C and Uracil Polyoxin C

  摘要：

  A short path synthesis of the cr-hydroxy esters (4 and 5) from the aldehyde (3) using (1-ethoxyvinyl)lithium and its application to the total syntheses of the pyrimidine nucleoside, thymine polyoxin C (1) and uracil polyoxin C (2), are described.

  DOI：

  10.3987/com-97-s30

文献信息

• (1-Ethoxyvinyl)lithium in the Total Synthesis Thymine Polyoxin C and Uracil Polyoxin C.
  作者：Hiroyuki AKITA、Kimio UCHIDA、Cheng Yu CHEN、Keisuke KATO

  DOI：10.1248/cpb.46.1034

  日期：——

  A short path synthesis of the ethyl (methyl 2, 3-O-isopropylidene-β-D-allofuranosid)uronate (5) and ethyl(methyl 2, 3-O-isopropylidene-α-L-talofuranosid)uronate (6) from methyl 2, 3-O-isopropylidene-β-D-ribopentodialdo-1, 4-furanoside (3) using (1-ethoxyvinyl)lithium and its application to the total synthesis of the pyrimidine nucleosides, thymine polyoxin C (1) and uracil polyoxin C (2), are described.

  描述了一种短步骤合成的方法，通过使用(1-乙氧基乙烯)锂，将甲基2, 3-O-异丙烯基-β-D-阿洛呋喃苷(3)转化为乙基(甲基2, 3-O-异丙烯基-β-D-阿洛呋喃糖尿酸酯)(5)和乙基(甲基2, 3-O-异丙烯基-α-L-塔罗呋喃糖尿酸酯)(6)，并将其应用于胸腺嘧啶多抗生素C (1)和尿嘧啶多抗生素C (2)的总合成。
• Glycosyl α-aminoacids via stereocontrolled buildup of a penaldic acid equivalent. An asymmetric synthesis of thymine polyoxin C
  作者：Philip Garner、Jung Min Park

  DOI：10.1016/s0040-4039(01)93448-3

  日期：——

  A new strategy for assembly of glycosyl α-aminoacids via the stereocontrolled buildup of a serine-derived penaldic acid equivalent (i.e. I → II) is illustrated by the asymmetric synthesis of thymine polyoxin C.

  胸腺嘧啶多恶菌素C的不对称合成说明了通过立体控制的丝氨酸衍生的戊二酸当量（即I → II）组装糖基α-氨基酸的新策略。
• Glycosyl .alpha.-amino acids via stereocontrolled buildup of a penaldic acid equivalent. A novel synthetic approach to the nucleosidic component of the polyoxins and related substances
  作者：Philip Garner、Jung Min Park

  DOI：10.1021/jo00299a017

  日期：1990.6
• GARNER, PHILIP;PARK, JUNG MIN, J. ORG. CHEM., 55,(1990) N2, C. 3772-3787
  作者：GARNER, PHILIP、PARK, JUNG MIN

  DOI：——

  日期：——
• An asymmetric approach to 5-O-carbamoyl-2-epi-polyoxamic acid and the total synthesis of 2′′-epi-polyoxin J
  作者：Yong-Chun Luo、Huan-Huan Zhang、Yao-Zong Liu、Rui-Ling Cheng、Peng-Fei Xu

  DOI：10.1016/j.tetasy.2009.03.033

  日期：2009.6

  A stereospecific synthetic approach to 5-O-carbamoyl-2-epi-polyoxamic acid has been developed. The asymmetric nucleophilic addition of 2-lithiofuran to a tert-butanesulfinyl imine was employed as the key step to construct the C-2 stereocenter and 2 ''-epi-polyoxin J has been synthesized for the first time. Significantly, the synthesis provides a facile method for the large scale and stereoselective preparation of 5-O-carbamoyl-2-epi-polyoxamic acid and some related diastereoisomers of polyoxins and its analogues because of its simple operation, excellent yield, and high stereoselectivity. This will be convenient for research of the polyoxins' structure-activity relationship and to search for more potent and effective anti-candidal agents. (C) 2009 Elsevier Ltd. All rights reserved.