(Peracetyltunicaminyl)uracil | 99441-18-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (Peracetyltunicaminyl)uracil
• 英文别名: α-Heptaacetyltunicaminyluracil；heptaacetyltunicaminyluracil；[(2R,3S,4R,5R,6R)-5-acetamido-4,6-diacetyloxy-2-[(2R)-2-acetyloxy-2-[(2R,3R,4R,5R)-3,4-diacetyloxy-5-(2,4-dioxopyrimidin-1-yl)oxolan-2-yl]ethyl]oxan-3-yl] acetate
• CAS: 99441-18-6
• 化学式: C₂₉H₃₇N₃O₁₇
• 分子量: 699.623
• InChiKey: BJUDFXPHTYYDHF-ZDYJVHMFSA-N

物化性质

• 密度：
  1.44±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.72
• 重原子数：
  49.0
• 可旋转键数：
  11.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  260.22
• 氢给体数：
  2.0
• 氢受体数：
  18.0

反应信息

• 作为产物：
  描述：

  Benzoic acid (2R,3R,4R)-2-[(R)-2-benzyloxymethoxy-2-((3aR,4R,6R,6aR)-6-methoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-ethyl]-4-hydroxy-3,4-dihydro-2H-pyran-3-yl ester 在 palladium hydroxide - carbon 吡啶 、 盐酸 、 4-二甲氨基吡啶 、 三氟甲磺酸三甲基硅酯 、 Lemieux azidonitrating reagent 、 硫酸 、 氢气 、 silver trifluoromethanesulfonate 、 potassium carbonate 、 三乙胺 、 三苯基膦 、 lithium bromide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 溶剂黄146 、 乙腈 为溶剂， 生成 (Peracetyltunicaminyl)uracil
  参考文献：
  名称：

  A fully synthetic route to tunicaminyluracil

  摘要：

  DOI：

  10.1021/ja00311a089

文献信息

• Total Synthesis of Tunicamycin V
  作者：Kazuki Yamamoto、Fumika Yakushiji、Takanori Matsumaru、Satoshi Ichikawa

  DOI：10.1021/acs.orglett.7b03623

  日期：2018.1.5

  The total synthesis of tunicamycin V is described. This strategy is based on the initial construction of tunicaminyluracil, which is regarded to play an important role in the observed biological activities. The key to the synthesis was a Mukaiyama aldol reaction followed by a furan-oxidation to construct the undecose skeleton, a [3,3] sigmatropic rearrangement of a cyanate, and a highly selective trehalose-type

  描述了衣霉素V的全合成。该策略基于衣氨酰尿嘧啶的初始构建，该构建被认为在观察到的生物活性中起重要作用。合成的关键是Mukaiyama aldol反应，然后进行呋喃氧化以构建十一碳烯骨架，氰酸酯的[3,3]σ重排以及高度选择性的海藻糖型糖基化。
• Fully synthetic stereoselective routes to the differentially protected subunits of the tunicamycins
  作者：Samuel J. Danishefsky、Shari L. DeNinno、Shu Hui Chen、Louise Boisvert、Michael Barbachyn

  DOI：10.1021/ja00197a047

  日期：1989.7

  La cyclocondensation d'un β-D-allo-heptodialdo-1,4 furanosyl-1 uracile issu de l'O-isopropylidene-2,3 uridine et d'un butadiene-1,3 donne un L-allo-α-D-galacto-undecodialdopyranose-1,5furanose-8,11yl uracile. Une seconde unite derivee d'un acetamido-2 glucopyranose est egalement synthetisee. Ceci constitue une synthese totale des intermediaires de Suami

  La cyclocondensation d'un β-D-allo-heptodialdo-1,4 furanosyl-1 uracile issu de l'O-isopropylidene-2,3 uridine et d'un butadiene-1,3 donne un L-allo-α-D -galacto-undecodialdopyranose-1,5furanose-8,11yl 尿嘧啶。Une seconde unite d'un acetamido-2 glupyranose est egalement synthetisee。Ceci constitue unesynthese totale des intermediaires de Suami
• Synthetic Studies of the Tunicamycin Antibiotics. Preparation of (+)-Tunicaminyluracil, (+)-Tunicamycin-V, and 5'-epi-Tunicamycin-V
  作者：Andrew G. Myers、David Y. Gin、Daniel H. Rogers

  DOI：10.1021/ja00090a018

  日期：1994.6

  A concise synthetic route to the tunicamycin antibiotics is described, illustrated by the preparation of (+)-tunicamycin-V (1-V). Key features of the synthesis include (1) the development and application of a silicon-mediated reductive coupling of aldehydes and allylic alcohols to construct the undecose core of the natural product and (2) the development of an efficient procedure for the synthesis of the trehalose glycosidic bond within the antibiotic. These innovations allow for the coupling of a uridine-derived aldehyde fragment with a performed trehalose-linked disaccharide allylic alcohol to form the carbohydrate core (1) of the natural product in a highly covergent manner. The resultant amino polyol is a versatile intermediate for the synthesis of any of the homologous tunicamycin antibiotics.
• DANISHEFSKY, SAMUEL J.;DENINNO, SHARI L.;CHEN, SHU-HUI;BOISVERT, LOUISE;B+, J. AMER. CHEM. SOC., 111,(1989) N5, C. 5810-5818
  作者：DANISHEFSKY, SAMUEL J.、DENINNO, SHARI L.、CHEN, SHU-HUI、BOISVERT, LOUISE、B+

  DOI：——

  日期：——