L-erythrono-1,4-lactone | 17675-99-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: L-erythrono-1,4-lactone
• 英文别名: L-erythronolactone；(3S,4S)-3,4-Dihydroxydihydrofuran-2(3H)-one；(3S,4S)-3,4-dihydroxyoxolan-2-one
• CAS: 17675-99-9
• 化学式: C₄H₆O₄
• 分子量: 118.089
• InChiKey: SGMJBNSHAZVGMC-HRFVKAFMSA-N

物化性质

• 熔点：
  101-102 °C
• 沸点：
  277.1±7.0 °C(Predicted)
• 密度：
  1.681±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  8
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  L-erythrono-1,4-lactone 在 羟胺 作用下， 反应 0.17h， 以40%的产率得到L-erythronohydroxamic acid
  参考文献：
  名称：

  A convenient preparation of aldonohydroxamic acids in water and crystal structure of l-erythronohydroxamic acid

  摘要：

  Hydroxamic acids derived from aldonic acids, namely aldonohydroxamic acids, have become an increasingly important class of inhibitors of enzymes involved in the metabolism of carbohydrates. We now report the straightforward preparation of various types of aldonohydroxamic acids by a new methodology involving the use of commercial 50% aqueous hydroxylamine as the source of the free base hydroxylamine that reacts directly with the corresponding aldonolactone dissolved in water. The reaction proceeds almost instantaneously in water at room temperature, yielding generally pure products in quantitative yield. To date, this methodology is probably the most facile and efficient way to synthesize aldonohydroxamic acids. We also determined by X-ray diffraction analysis the first crystal structure of a free aldonohydroxamic acid reported to date. Crystals of L-erythronohydroxamic acid belonged to the monoclinic system, space group P2(1), a = 5.511(3), b = 7.556(1), c = 8.071(3) Angstrom, beta = 109.10 degrees, and Z = 2. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(01)00210-5
• 作为产物：
  描述：

  erythronic acid 100.0 ℃ 、2.0 kPa 条件下， 生成 L-erythrono-1,4-lactone
  参考文献：
  名称：

  Nef, Justus Liebigs Annalen der Chemie, 1907, vol. 357, p. 248

  摘要：

  DOI：

文献信息

• A New Efficient Access to Glycono-1,4-lactones by Oxidation of Unprotected Itols by Catalytic Hydrogen Transfer with RhH(PPh₃)₄-Benzalacetone System
  作者：I. Isaac、G. Aizel、I. Stasik、A. Wadouachi、D. Beaupère

  DOI：10.1055/s-1998-1705

  日期：1998.5

  Treatment of unprotected pentitols and hexitols with RhH(PPh3)4-benzalacetone system leads exclusively to glycono-1,4-lactones in 60-96% yield.

  使用RhH(PPh3)4-苯甲醛乙酮体系处理未保护的戊糖醇和己糖醇，可专一性地以60-96%的产率生成糖醛-1,4-内酯。
• High yield protection of alcohols, including tertiary and base sensitive alcohols, as benzhydryl ethers by heating with diphenyldiazomethane in the absence of any other reagent
  作者：Daniel Best、Sarah F. Jenkinson、Sebastian D. Rule、Rosemary Higham、Thomas B. Mercer、Richard J. Newell、Alexander C. Weymouth-Wilson、George W.J. Fleet、Sigthor Petursson

  DOI：10.1016/j.tetlet.2008.02.042

  日期：2008.3

  can be introduced efficiently without the need for any acid or base catalysis and which is not prone to acid or base catalysed migration is a significant advantage for many syntheses. Benzhydryl [diphenylmethyl] ethers of sugar lactones are formed in high yield under neutral conditions when the corresponding alcohol is heated with diphenyldiazomethane in an inert solvent such as acetonitrile or toluene;

  对于许多合成而言，可在不需要任何酸或碱催化的情况下有效地引入保护基且不易于被酸或碱催化的迁移的保护基是重要的优点。当相应的醇与二苯基重氮甲烷在惰性溶剂（如乙腈或甲苯）中加热时，在中性条件下，糖内酯的苄基[二苯基甲基]醚可以高收率形成；这样就可以在没有任何其他试剂的情况下轻松保护对碱敏感的和高度受阻的叔醇。
• カルボン酸塩、カルボン酸発生剤、レジスト組成物及びレジストパターンの製造方法
  申请人：住友化学株式会社

  公开号：JP2018135323A

  公开（公告）日：2018-08-30

  【課題】良好なＣＤ均一性（ＣＤＵ）でレジストパターンを製造することができる塩及びレジスト組成物を提供することを目的とする。【解決手段】式（Ｉ）で表されるカルボン酸塩、該塩を含む酸発生剤及びレジスト組成物。［式中、Ｘa及びＸbは、それぞれ独立に、酸素原子又は硫黄原子を表す。環Ｗは、エステル結合又はチオエステル結合を環の構成に含む複素環を表し、さらに、該複素環に含まれる−ＣＨ２−は、−Ｏ−、−Ｓ−、−ＣＯ−等で置き換わっていてもよく、該複素環に含まれる水素原子は、ヒドロキシ基、シアノ基、カルボキシ基、アルキル基、アルコキシ基、アルコキシカルボニル基等及びこれらを組み合わせた基で置換されていてもよい。Ｘ１は、置換基を有してもよい炭化水素基を表し、該炭化水素基に含まれる−ＣＨ2−は、−Ｏ−、−Ｓ−、−ＣＯ−等に置き換わっていてもよい。Ｚ＋は有機カチオンを表す。］【選択図】なし

  这项技术旨在提供能够制造具有良好CD均一性（CDU）的光刻胶图案的盐和光刻胶组合物。解决方案包括由式（I）表示的羧酸盐、含有该盐的酸发生剂和光刻胶组合物。【式中，Xa和Xb分别独立表示氧原子或硫原子。环W表示包含酯键或硫酯键的环构造的复杂环，并且在该复杂环中包含的-CH2-可以被-O-、-S-、-CO-等取代，该复杂环中的氢原子可以被羟基、氰基、羧基、烷基、烷氧基、烷氧羰基等及其组合取代。X1表示可以带有取代基的碳氢基，该碳氢基中包含的-CH2-可以被-O-、-S-、-CO-等取代。Z+表示有机阳离子。】【选择图】无
• Regioselective Tosylation of Aldonolactones
  作者：Inge Lundt、Robert Madsen

  DOI：10.1055/s-1992-26320

  日期：——

  An investigation of the selective di-O-acylation with p-toluenesulfonyl (tosyl) chloride of the four D-pentono-, the eight D-hexono-and D-glycero-D-gulo-heptonolactone has been undertaken, and a number of 2,5-, 2,6- and 2,7-di-O-tosylated lactones have been prepared. Monotosylation of L-erythrono- and L-rhamnonolactone gave the corresponding 2-O-tosylates.

  对四种D-pentono、八种D-hexono和D-glycero-D-gulo-heptonolactone进行选择性二-O-酰化的研究已开展，并已制备出多种2,5-、2,6-和2,7-二-O-托烯基化的内酯。对L-红酮酸内酯和L-鼠李糖内酯的单托烯基化反应得到了相应的2-O-托烯基化产物。
• Synthesis and antiviral activity of stereoisomeric eritadenines
  作者：Antonín Holý、Ivan Votruba、Erik De Clercq

  DOI：10.1135/cccc19821392

  日期：——

  D-Eritadenine (Ia) and L-eritadenine (IIa) were prepared from 5-(adenin-9-yl)-5-deoxyaldofuranoses or enantiomeric 2,3-disubstituted erythronolactones (VIIIb, c, XIV). Oxidation of methyl 2,3-O-isopropylidene-D-ribofuranoside (IX) with periodate in the presence of ruthenium, followed by acid hydrolysis and reduction with sodium borohydride, afforded L-ribonolactone (XI). Its 2,3-O-isopropylidene derivative was subjected to alkaline hydrolysis, followed by oxidation with periodate, reduction with sodium borohydride and reaction with cyclohexanone to give 2,3-O-cyclohexylidene-L-erythronolactone (XIV). Condensation of [U-¹⁴C]-adenine with VIIIb, followed by acid hydrolysis, afforded [U-¹⁴C-adenine]-D-eritadenine. The threo-eritadenines III and IV were prepared by oxidation of 1-(adenin-9-yl)-1-deoxy-2,3-O-isopropylidenethreitols XVI and XVII with sodium periodate in the presence of ruthenium, followed by acid hydrolysis. Reaction of 9-(2,2-diethoxyethyl)adenine (XIX) with malonic acid gave 4-(adenin-9-yl)-3-butenoic acid (XXI); its methyl ester XXII, prepared by treatment with methanol, was isomerized with triethylamine to give methyl 4-(adenin-9-yl)-2-butenoate (XXIII). Hydroxylation of XXIII with osmium tetroxide afforded the racemic mixture of D- and L-threo-eritadenine (III+ IV). Eritadenines Ia and IIa were active against vaccinia, measles and vesicular stomatitis virus. Eritadenine Ia was also effective against reo- and parainfluenza virus. In general, the antiviral activity of the eritadenines decreased in the order D-erythro (Ia) > L-erythro (IIa) > D- and L-threo (III, IV).

  D-厄利他呋喃核苷（Ia）和L-厄利他呋喃核苷（IIa）是从5-(腺嘌呤-9-基)-5-脱氧醛糖或对映异构的2,3-二取代的赤霉糖内酯（VIIIb, c, XIV）制备而成。使用高碘酸盐在钌的存在下氧化甲基2,3-O-异丙基-D-核糖呋喃苷（IX），随后进行酸水解和硼氢化钠还原，得到L-核糖内酮（XI）。将其2,3-O-异丙基衍生物经过碱水解，随后经过高碘酸盐氧化、硼氢化钠还原和与环己酮反应，得到2,3-O-环己基-L-赤霉糖内酯（XIV）。[U-14C]-腺嘌呤与VIIIb缩合，经过酸水解，得到[U-14C-腺嘌呤]-D-厄利他呋喃核苷。通过高碘酸盐在钌的存在下氧化1-(腺嘌呤-9-基)-1-脱氧-2,3-O-异丙基脱氢醇（XVI）和（XVII），得到threo-厄利他呋喃核苷III和IV。9-(2,2-二乙氧基乙基)腺嘌呤（XIX）与丙二酸反应，得到4-(腺嘌呤-9-基)-3-丁烯酸（XXI）；经过甲醇处理制备其甲酯（XXII），再与三乙胺异构化，得到甲基4-(腺嘌呤-9-基)-2-丁烯酸酯（XXIII）。XXIII的羟化反应得到D-和L-厄利他呋喃核苷的外消旋混合物（III+IV）。厄利他呋喃核苷Ia和IIa对牛痘病毒、麻疹病毒和水疱性口炎病毒具有活性。厄利他呋喃核苷Ia也对副流感病毒和副流感病毒有效。总体而言，厄利他呋喃核苷的抗病毒活性按照D-赤霉糖（Ia） > L-赤霉糖（IIa） > D-和L-threo（III, IV）的顺序递减。