2,3-(isopropylidenedioxy)-4,4-dihydroxybutanic acid lactone

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3-(isopropylidenedioxy)-4,4-dihydroxybutanic acid lactone
• 英文别名: 2,3-O-isopropylidene-L-erythruronolactone；2,3-O-isopropylidene-D-erythruronolactone；(3aS,6aR)-6-hydroxy-2,2-dimethyl-6,6a-dihydro-3aH-furo[3,4-d][1,3]dioxol-4-one
• 化学式: C₇H₁₀O₅
• 分子量: 174.153
• InChiKey: UPFMNKGFLNXERP-OVEKKEMJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,3-(isopropylidenedioxy)-4,4-dihydroxybutanic acid lactone 在 sodium tetrahydroborate 、 二异丁基氢化铝 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 2,3-O-isopropylidene-L-erythrofuranose
  参考文献：
  名称：

  An enantiodivergent approach to D- and L-erythrose via microbial oxidation of chlorobenzene

  摘要：

  DOI：

  10.1016/s0040-4039(00)99319-5
• 作为产物：
  描述：

  (3aS,7aS)-4-chloro-2,2-dimethyl-3a,7a-dihydro-1,3-benzodioxole 在 potassium permanganate 、 sodium periodate 、 水 、 magnesium sulfate 作用下， 以 水 、 丙酮 为溶剂， 反应 4.25h， 生成 2,3-(isopropylidenedioxy)-4,4-dihydroxybutanic acid lactone
  参考文献：
  名称：

  From Chlorobenzene to a Carbohydrate in Two Steps. A New Chemoenzymatic Synthesis of 2,3-O-Isopropylidene-D-erythruronolactone

  摘要：

  氯环氧乙烷 V 被两当量的碘酸钠控制氧化，得到2,3-O-异丙基-D-赤藓糖内酯 (I)，收率为63%。该方法通过保护二醇 III、将缩醛 IV 氧化为 V，然后将其氧化裂解为 I，在中等规模下一次操作中产生了标题内酯，收率为51%。内酯 I 的制备详细程序和物理常数已提供。

  DOI：

  10.1135/cccc19932517

文献信息

• Improved Practical Synthesis of a Prostaglandin and Carbocyclic Nucleoside Synthon
  作者：Tomas Hudlicky、Michael G. Natchus、Thomas C. Nugent

  DOI：10.1080/00397919208021086

  日期：1992.1

  An efficient, four step synthesis of chiral enone 2a [(+)-2,3-(isopropylidenedioxy)-4-cyclopentenone] from diol 1a (X = Cl), available from microbial oxidation of chlorobenzene, is described. This synthesis is a vast improvement over that previously reported and compares very favorably with others in the literature.
• An enantiodivergent approach to D- and L-erythrose via microbial oxidation of chlorobenzene
  作者：Tomas Hudlicky、Hector Luna、John D. Price、Fan Rulin

  DOI：10.1016/s0040-4039(00)99319-5

  日期：1989.1
• Dipeptide isosteres. 1. Synthesis of dihydroxyethylene dipeptide isosteres via diastereoselective additions of alkyllithium reagents to N,N-dimethylhydrazones. Preparation of renin and HIV-1 protease inhibitor transition-state mimics
  作者：William R. Baker、Stephen L. Condon

  DOI：10.1021/jo00064a013

  日期：1993.6

  The amino and diamino dihydroxyethylene dipeptide isosteres 19a,b and 23 are important intermediates for the preparation of inhibitors of human renin and HIV-1 protease, respectively. A general synthetic strategy was developed to access both dipeptide isosteres. The key step was a diastereoselective addition of an alkyllithium reagent to an aldehyde hydrazone. Thus, isosteres 19a and 19b were synthesized by addition of either benzyllithium or (cyclohexylmethyl)lithium to (4S,5R)-2,2-dimethyl-4-(2-methylpropan-1-yl)-5-formyl-1,3-dioxolane N,N-dimethylhydrazone (4) in diethyl ether at -10-degrees-C. The hydrazine addition product was reduced to the amine, and the acetonide protecting group was removed. The resulting amino diol was derivatized as either a N-Boc analogue or coupled to N-(tert-butyloxycarbonyl)-3-(thiazol-4-yl)alanine. The addition reactions were completely diastereoselective, affording only the chelation-controlled products (beta attack, S configuration at C(2)). Hydrazone 4 was prepared from either D-isoascorbic acid (1), divinyl carbinol (5), or chlorobenzene (9). Application of the hydrazone/alkyllithium reaction to the synthesis of the diamino dihydroxyethylene dipeptide isostere 23 was also achieved. Reaction of the bis-hydrazone 22 with benyllithium, followed by Raney nickel reduction of the hydrazine addition product, formation of the bis-benzyl carbamate, and deprotection of the acetonide with methanolic HCI gave the diamino dihydroxyethylene dipeptide isostere 23 in 36 % overall yield (four steps). Isostere 23 is an intermediate useful for the preparation Of C2 symmetric HIV-1 protease inhibitors.
• HUDLICKY, TOMAS;LUNA, HECTOR;PRICE, JOHN D.;RULIN, FAN, TETRAHEDRON LETT., 30,(1989) N1, C. 4053-4054
  作者：HUDLICKY, TOMAS、LUNA, HECTOR、PRICE, JOHN D.、RULIN, FAN

  DOI：——

  日期：——
• Combinatorial library approach to iminocyclitols with biological activity
  申请人：Moriarty Robert M.

  公开号：US20090182154A1

  公开（公告）日：2009-07-16

  A method of synthesizing stereochemically defined iminocyclitol comprises replacing an intraring oxygen in a cyclic sugar by an intraring imine to form an iminocyclitol, wherein said iminocyclitol has a defined stereochemical configuration different from a stereochemical configuration of the cyclic sugar. The invention also provides combinatorial libraries of iminocyclitol compounds, allowing for diverse C1 and N-substitution. In addition, provided are methods of treating viral infections with iminocyclitols compounds.