(3R,4S,5R)-3,4-diacetoxy-5-acetoxymethyl-2-tetrahydrofuranone | 79580-60-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (3R,4S,5R)-3,4-diacetoxy-5-acetoxymethyl-2-tetrahydrofuranone
• 英文别名: 3R,4S,5R-3,4-diacetoxy-5-acetoxymethyl-2-tetrahydrofuranone；tri-O-acetyl-D-xylono-1,4-lactone；D-xylono-1,4-lactone；O²,O³,O⁵-triacetyl-D-xylonic acid-lactone；O²,O³,O⁵-Triacetyl-D-xylonsaeure-lacton；D-Xylonic acid, |A-lactone, 2,3,5-triacetate；[(2R,3S,4R)-3,4-diacetyloxy-5-oxooxolan-2-yl]methyl acetate
• CAS: 79580-60-2
• 化学式: C₁₁H₁₄O₈
• 分子量: 274.227
• InChiKey: JIILXWRHIYAEQM-KXUCPTDWSA-N

物化性质

• 熔点：
  97-98 °C
• 沸点：
  309.2±31.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  105
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (3R,4S,5R)-3,4-diacetoxy-5-acetoxymethyl-2-tetrahydrofuranone 在 palladium on activated charcoal 氢氧化钾 、 diisoamyl borane 、 氢气 、 三乙胺 、 乙酰氯 作用下， 以 四氢呋喃 、 乙醇 、 乙酸乙酯 为溶剂， 25.0 ℃ 、303.98 kPa 条件下， 反应 48.0h， 生成 methyl 3-deoxy-α-D-threo-pentofuranoside
  参考文献：
  名称：

  Bock, Klaus; Lundt, Inge; Pedersen, Christian, Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1981, vol. 35, # 3, p. 155 - 162

  摘要：

  DOI：
• 作为产物：
  描述：

  D-吡喃木糖 在 溴 、 potassium carbonate 作用下， 以 水 、 溶剂黄146 为溶剂， 反应 0.5h， 生成 (3R,4S,5R)-3,4-diacetoxy-5-acetoxymethyl-2-tetrahydrofuranone
  参考文献：
  名称：

  Synthesis of 1-(2,3-dideoxy-2-fluoro-.beta.-D-threo-pentofuranosyl)cytosine (F-ddC). A promising agent for the treatment of acquired immune deficiency syndrome

  摘要：

  A new and practical synthesis of a fluorinated analogue of 2',3'-dideoxycytidine (ddC), 1-(2,3-dideoxy-2-fluoro-beta-D-threo-pentofuranosyl)cytosine (F-ddC), is described. The key feature in the synthesis is the use of the selectively protected 2,4,5-trihydroxypentanoic acid derivative 15 as a chiral pool synthon.

  DOI：

  10.1021/jo00014a013

文献信息

• A Chiron Approach to the Total Synthesis of (+)-Aculeatin D
  作者：Zhi-Bin Zhen、Jian Gao、Yikang Wu

  DOI：10.1021/jo801296x

  日期：2008.9.19

  A synthesis of natural aculeatin D has been achieved, with the key stereogenic centers taken from inexpensive and readily available D-xylose. In elaboration of D-xylose into a desired form readily applicable in synthesis a previously misinterpreted and overlooked abnormal selectivity in hydroxyl protection was noticed and exploited. Protocols were developed for monotosylation of a triol insoluble in

  已经实现了天然针叶苷D的合成，其中关键的立体异构中心取自廉价且容易获得的D-木糖。在将D-木糖精加工成易于适用于合成的所需形式时，注意到并利用了先前被误解和忽视的羟基保护的异常选择性。已开发出分别在PIFA介导的氧化螺环化反应中不溶于CH2Cl2的三醇单甲苯基化和“冻结”不太稳定的异构体（aculeatin D）的方案。还解决了文献中热力学上更稳定的二噻吩碳负离子在苄基保护基上的无法解释的去质子化。
• Process for the preparation of a fluorotetrahydrofuranone derivative
  申请人：F. HOFFMANN-LA ROCHE AG

  公开号：EP0463470A2

  公开（公告）日：1992-01-02

  (5S)-3-Fluoro-tetrahydro-5-[(hydroxy)methyl] -2(3H)-furanone, a known intermediate for the manufacture of fluorodideoxytidine, is prepared from starting materials that are derived from D-pentoses, particularly D-xylose.

  (5S)-3-氟-四氢-5-[(羟基)甲基]-2(3H)-呋喃酮是一种已知的生产氟代脱氧胞苷的中间体，它是由来自 D-戊糖，特别是 D-木糖的起始原料制备的。
• A general synthetic route to A-ring hydroxylated vitamin D analogs from pentoses
  作者：Robert M. Moriarty、Joonggon Kim、Harry Brumer

  DOI：10.1016/0040-4039(94)02209-t

  日期：1995.1

  The enzyne needed for coupling to a CD-ring fragment, namely, 3S, 5R-oct-1-en-7-yne-3,5-diol, in the Trost-Dumas carbopalladation route to 1 alpha, 25-dihydroxyvitamin D-3 was synthesized from D-xylose in 13 steps and 21% yield.
• Wu, Yong; Guan, Mei, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1998, vol. 37, # 9, p. 844 - 846
  作者：Wu, Yong、Guan, Mei

  DOI：——

  日期：——
• Unexpected outcome in the reaction of sugar lactones with iodotrimethylsilane
  作者：M.P. Heck、S. Monthiller、C. Mioskowski、J.P. Guidot、T. Le Gall

  DOI：10.1016/s0040-4039(00)73521-0

  日期：1994.7

  The reaction of iodotrimethylsilane with sugar lactones protected by ester groups leads to primary iodides of the same configuration.