methyl 2,4-dibromo-2,4-dideoxy-L-erythronate | 88824-11-7
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物化性质
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计算性质
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ADMET
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安全信息
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SDS
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制备方法与用途
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上下游信息
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文献信息
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表征谱图
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同类化合物
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相关功能分类
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相关结构分类
物化性质
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沸点：120-121 °C(Press: 2.0 Torr)
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密度：1.982±0.06 g/cm3(Predicted)
计算性质
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辛醇/水分配系数(LogP)：1.1
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重原子数：10
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可旋转键数：4
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环数：0.0
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sp3杂化的碳原子比例：0.8
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拓扑面积：46.5
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氢给体数：1
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氢受体数：3
上下游信息
反应信息
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作为反应物：描述：methyl 2,4-dibromo-2,4-dideoxy-L-erythronate 在 palladium on activated charcoal 氢气 、 sodium acetate 作用下， 以 溶剂黄146 、 乙酸乙酯 为溶剂， 反应 1.0h， 以70%的产率得到methyl (R)-4-bromo-3-hydroxybutyrate参考文献：名称：Synthesis of S- and R-4-Amino-3-hydroxybutyric Acid (GABOB) and S- and R-Carnitine from Arabinose or Ascorbic Acid.摘要：DOI：10.3891/acta.chem.scand.37b-0341
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作为产物：描述：甲醇 、 calcium L-threonate 在 氢溴酸 、 溶剂黄146 作用下， 反应 24.0h， 以90.2%的产率得到methyl 2,4-dibromo-2,4-dideoxy-L-erythronate参考文献：名称：Cyclic hydroxamates, especially multiply substituted [1,2]oxazinan-3-ones摘要：报道了将假定的N-酰-D-阿拉-D-阿拉替代物的合成途径，从将4、5和6元环内酯转化为5、6和7元环氢氧化物开始。合成的关键步骤是ω-氨氧酯的三甲基铝促进的环化反应。7元环氢氧化物以椅式构象结晶。将反应序列扩展到同型丝氨酸或同型丝氨酸内酯会导致环康纳林和N-酰化环康纳林的形成。环康纳林的4-苯乙酰氨基衍生物以船式构象结晶。在环康纳林的4-酰氨基环康纳林的环氮上附加2-羧基丙基取代基，可以通过将无环氨氧酯前体与苄乳酸三甲酯的三氟甲磺酸酯偶联，或在环化之后，通过与三氟甲基丙酸叔丁酯在氟化钾-氧化铝存在下偶联，然后在每种情况下去除保护基来实现。通过4-苯乙酰氨基环康纳林与苄基2-氧戊二酸酯在异亚胺存在下反应，然后进行氢解，合成了抗生素拉维西汀的六元同系物。从甲基2,4-二溴-2,4-二去氧-L-赤葡萄糖酸甲酯开始，该物质可以从抗坏血酸中经过两步合成，这些反应序列已被应用于立体特异性合成一种D-丙氨酸衍生物，其氮原子被包含在一个3,4-二取代[1,2]噁唑烷-3-酮内。关键词：D-ala-D-ala替代物，环康纳林，同型拉维西汀，肽聚糖，三甲基铝。DOI：10.1139/v03-122
文献信息
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Method for synthesizing oxazinones申请人：——公开号：US20030232820A1公开（公告）日：2003-12-18New methods and intermediates are discussed for the stereospecific synthesis of oxazinone compounds.讨论了用于氧杂环酮化合物立体特异合成的新方法和中间体。
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Deoxyiminoalditols from Aldonic Acids VI. Preparation of the Four Stereoisomeric 4-Amino-3-hydroxypyrrolidines from Bromodeoxytetronic Acids. Discovery of a New α-Mannosidase Inhibitor作者：Gerrit Limberg、Inge Lundt、John ZavillaDOI：10.1055/s-1999-3680日期：1999.1A convenient four step synthesis of 4-amino-3-hydroxy-pyrrolidines is presented. From the readily available d- and l-tetronic acids the four possible stereoisomeric 4-amino-3-hydroxy-pyrrolidines 14 (3R,4R), 15 (3R,4S), ent-14 (3S,4S) and ent-15 (3S,4R) could be obtained as crystalline compounds, avoiding any chromatographic purification. The key step in the reactions was the regioselective formation of either the 2,4-diamino-2,4-di-deoxy-d-threono-1,4-lactam (5) or the 3,4-diamino-3,4-dideoxy-l-erythrono-1,4-lactam (10) by treatment of the methyl 4-bromo-4-deoxy-2,3-cis- or -2,3-trans-anhydrotetronates (3 or 9), respectively, with liquid ammonia. Thus, opposite regioselectivity for the opening of the cis-configurated epoxide 3 (4 : 1, C-2/C-3) and the trans-configurated epoxide 9 (3 : 7, C-2/C-3) by ammonia was observed. Preliminary testing as glycosidase inhibitors of the 4-amino-3-hydroxypyrrolidines formed by reduction of the lactams showed an inhibition of α-mannosidase (Ki 40 μM) by isomer 14, (3R,4R)-4-amino-3-hydroxypyrrolidine.提出了 4-氨基-3-羟基-吡咯烷的便捷四步合成。从容易获得的 d-和 l-特窗酸中可以得到四种可能的立体异构体 4-氨基-3-羟基-吡咯烷 14 (3R,4R)、15 (3R,4S)、ent-14 (3S,4S) 和 ent-15 (3S,4R)可以作为结晶化合物获得，避免任何色谱纯化。反应的关键步骤是区域选择性形成 2,4-二氨基-2,4-二-脱氧-d-苏酮-1,4-内酰胺 (5) 或 3,4-二氨基-3,4通过分别处理4-溴-4-脱氧-2,3-顺式-或-2,3-反式-脱水四酮酸甲酯(3或9)，得到-二脱氧-L-赤式-1,4-内酰胺(10) ，用液氨。因此，氨对顺式环氧化物 3 (4:1, C-2/C-3) 和反式环氧化物 9 (3:7, C-2/C-3) 的开环具有相反的区域选择性。观察到。作为通过内酰胺还原形成的 4-氨基-3-羟基吡咯烷的糖苷酶抑制剂的初步测试显示异构体 14，(3R,4R)-4-氨基-3-羟基吡咯烷对 α-甘露糖苷酶 (Ki 40 μM) 具有抑制作用。
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A novel synthesis of the monobactam antibiotic carumonam作者：Percy S. Manchand、Kin Chun Luk、Peter S. Belica、Satish C. Choudhry、Chung Chen Wei、Milan SoukupDOI：10.1021/jo00258a020日期：1988.11
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MANCHAND, PERCY S.;LUK, KIN-CHUN;BELICA, PETER S.;CHOUDHRY, SATISH C.;WEI+, J. ORG. CHEM., 53,(1988) N 23, C. 5507-5512作者：MANCHAND, PERCY S.、LUK, KIN-CHUN、BELICA, PETER S.、CHOUDHRY, SATISH C.、WEI+DOI：——日期：——
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Cyclic hydroxamates, especially multiply substituted [1,2]oxazinan-3-ones作者：Saul Wolfe、Marie-Claire Wilson、Ming-Huei Cheng、Gennady V Shustov、Christiana I AkucheDOI：10.1139/v03-122日期：2003.8.1
Routes to putative N-acyl-D-ala-D-ala surrogates, beginning with the conversion of 4-, 5-, and 6-membered lactones into 5-, 6-, and 7-membered cyclic hydroxamates, are reported. The key step of the synthesis is trimethylaluminium-promoted cyclization of an ω-aminooxyester. The 7-membered cyclic hydroxamate crystallizes in a chair conformation. Extension of the reaction sequence to homoserine or homoserine lactone leads to cyclocanaline and N-acylated cyclocanalines. The 4-phenylacetamido derivative of cyclocanaline crystallizes in a boat conformation. The attachment of a 2-carboxypropyl substituent to the ring nitrogen of a 4-acylaminocyclocanaline has been effected, prior to cyclization, by coupling of the acyclic aminooxyester precursor to the triflate of benzyl lactate or, after cyclization, by coupling to tert-butyl α-bromopropionate in the presence of potassium fluoride alumina, followed by removal of the protecting group in each case. A six-membered homolog of the antibiotic lactivicin has been synthesized by the reaction of 4-phenylacetamidocyclocanaline with benzyl 2-oxoglutarate in the presence of carbodiimide, followed by hydrogenolysis. Starting with methyl 2,4-dibromo-2,4-dideoxy-L-erythronate, which is available in two steps from L-ascorbic acid, these reaction sequences have been applied to the stereospecific synthesis of a D-alanine derivative whose nitrogen atom is enclosed within a 3,4-disubstituted [1,2]oxazinan-3-one. Key words: D-ala-D-ala surrogate, cyclocanaline, homolactivicin, peptidoglycan, trimethylaluminium.
报道了将假定的N-酰-D-阿拉-D-阿拉替代物的合成途径，从将4、5和6元环内酯转化为5、6和7元环氢氧化物开始。合成的关键步骤是ω-氨氧酯的三甲基铝促进的环化反应。7元环氢氧化物以椅式构象结晶。将反应序列扩展到同型丝氨酸或同型丝氨酸内酯会导致环康纳林和N-酰化环康纳林的形成。环康纳林的4-苯乙酰氨基衍生物以船式构象结晶。在环康纳林的4-酰氨基环康纳林的环氮上附加2-羧基丙基取代基，可以通过将无环氨氧酯前体与苄乳酸三甲酯的三氟甲磺酸酯偶联，或在环化之后，通过与三氟甲基丙酸叔丁酯在氟化钾-氧化铝存在下偶联，然后在每种情况下去除保护基来实现。通过4-苯乙酰氨基环康纳林与苄基2-氧戊二酸酯在异亚胺存在下反应，然后进行氢解，合成了抗生素拉维西汀的六元同系物。从甲基2,4-二溴-2,4-二去氧-L-赤葡萄糖酸甲酯开始，该物质可以从抗坏血酸中经过两步合成，这些反应序列已被应用于立体特异性合成一种D-丙氨酸衍生物，其氮原子被包含在一个3,4-二取代[1,2]噁唑烷-3-酮内。关键词：D-ala-D-ala替代物，环康纳林，同型拉维西汀，肽聚糖，三甲基铝。
同类化合物
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