methyl (2S,3S)-2-azido-3-hydroxy-3-phenylpropionate | 133179-94-9

• 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: methyl (2S,3S)-2-azido-3-hydroxy-3-phenylpropionate
• 英文别名: (2S,3S)-2-azido-3-phenyl-3-hydroxypropionic acid methyl ester；methyl (2S,3S)-2-azido-3-hydroxy-3-phenylpropanoate
• CAS: 133179-94-9
• 化学式: C₁₀H₁₁N₃O₃
• 分子量: 221.216
• InChiKey: OWOFSTZBLZMVEP-IUCAKERBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  60.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl (2S,3S)-2-azido-3-hydroxy-3-phenylpropionate 在 palladium on activated charcoal 氢气 、 三乙胺 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 2.33h， 生成 methyl (2S,3S)-2-((tert-butyloxycarbonyl)amino)-3-((methanesulfonyl)oxy)-3-phenylpropionate
  参考文献：
  名称：

  Enantioselective routes to protected syn- and anti-.beta.-phenylcysteines

  摘要：

  DOI：

  10.1021/jo00038a048
• 作为产物：
  描述：

  甲基 (2R,3S)-(+)-2,3-二羟基-3-苯基丙酸盐 在 sodium azide 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 22.0h， 生成 methyl (2S,3S)-2-azido-3-hydroxy-3-phenylpropionate
  参考文献：
  名称：

  L-异缬氨酸生物合成中氮丙啶形成 α-酮戊二酸依赖性加氧酶的表征

  摘要：

  体外证明了Tolypocladium inflatum中 TqaLFM -ti的l-异缬氨酸生物合成。对α-酮戊二酸依赖性加氧酶TqaL -ti的生化分析表明，它从l-异亮氨酸产生( 2S , 3S )-3-乙基-3-甲基氮丙啶-2-羧酸，从而表现出与那些不同的立体选择性。所报道的同系物。值得注意的是，TqaL- ti中 I295 的单个突变完全改变了其立体选择性，产生了 C-3 立体异构体。 TqaFM- ti从 (2 S ,3 R )-氮丙啶-2-羧酸生成d -异缬氨酸，这表明 TqaL 产物的立体化学定义了异缬氨酸的立体化学。

  DOI：

  10.1021/acs.orglett.3c04185

文献信息

• Chemo-enzymatic synthesis of all isomeric 3-phenylserines and -isoserines
  作者：H. Hönig、P. Seufer-Wasserthal、H. Weber

  DOI：10.1016/s0040-4020(01)90519-8

  日期：1990.1

  prepared from cinnamic acid derivatives or via aldol condensations of benzaldehyde and suitable enolates in few steps. These racemates were resolved with lipases from Candida cylindracea (CC) and Pseudomonas fluorescens (P) and the obtained products were hydrogenated to 3-phenylserines and -isoserines. The influence of the acyl group in the enzymatic resolution of erythro-3-azido-2-acyloxy-3-phenylpropionic

  提供了对映体纯形式的3-苯基丝氨酸和3-苯基异丝氨酸的所有异构体的合成。非对映体纯离析物（苏/赤-2--叠氮基-3-丁酰氧基-3-苯基丙酸酯，苏/赤-3-叠氮--2-丁酰氧基-3-苯基丙酸酯，苏二-2-丁酰基氨基-3-丁酰氧基-由肉桂酸衍生物或通过苯甲醛与合适的烯醇酸酯的醛醇缩合在几个步骤中制备3-苯基丙酸酯，赤型-3-丁酰基氨基-2-丁酰基氧基-3-苯基丙酰胺。用消旋假丝酵母和荧光假单胞菌的脂肪酶分离了这些外消旋体（P）并将获得的产物氢化成3-苯基丝氨酸和-异丝氨酸。研究了酰基对赤型-3-叠氮基-2-酰氧基-3-苯基丙酸酯的酶促拆分的影响。
• Cyclic anti-aggregatory peptides
  申请人：SmithKline Beecham Corporation

  公开号：US05643872A1

  公开（公告）日：1997-07-01

  This invention relates to compounds of the formula: ##STR1## wherein: A' is absent, Asn, Gln, Ala or Abu; A is absent or a D- or L-amino acid chosen from Arg, HArg, (Me.sub.2)Arg, (Et.sub.2)Arg, Abu, Ala, Gly, His, Lys, or an .alpha.-R' substituted derivative thereof, Dtc, Tpr and Pro; B is a D- or L-amino acid chosen from Arg, HArg, NArg, (Me.sub.2)Arg, (Et.sub.2)Arg and Lys or an .alpha.-R' substituted derivative thereof; Q is absent or a D or L amino acid chosen from Tyr, (Alk)Tyr, Phe, (4'W)Phe, HPhe, Phg, Pro, Trp, His, Ser, (Alk)Ser, Thr, (Alk)Thr, (Alk)Cys, (Alk)Pen, Ala, Val, Nva, Met, Leu, Ile, Nle and Nal, or an .alpha.-R' substituted derivative thereof; M is absent or Gly or a D- or L-amino acid chosen from Glu, Phe, Pro, Lys and Ser or, provided n is 1, B-Gly-Glu-Q; W is halogen or Alk; R' is Alk or PhCH.sub.2 ; ##STR2## wherein Z.sub.1 and Z.sub.2 are linked via a covalent bond between L.sup.1 and L.sup.2 ; or Z.sub.1 and Z.sub.2 are, taken together, a covalent bond between the amino terminal residue and the carboxy terminal residue; L.sup.1 and L.sup.2 are --S-- or --(CH.sub.2).sub.p --; X is R.sub.4 R.sub.5 N or H; Y is H, CONR.sub.1 R.sub.2 or CO.sub.2 R.sub.2 ; R.sub.1 and R.sub.2 are H, Alk or (CH.sub.2).sub.p Ar; R.sub.3 and R.sub.3' are H, Alk, (CH.sub.2).sub.p Ar or taken together are --(CH.sub.2).sub.4 -- or --(CH.sub.2).sub.5 --; R.sub.4 is H or Alk; R.sub.5 is R.sub.11, R.sub.11 CO, R.sub.11 OCO, R.sub.11 OCH(R.sub.11')CO, R.sub.11 NHCH(R.sub.11')CO, R.sub.11 SCH(R.sub.11')CO, R.sub.11 SO.sub.2 or R.sub.11 SO; R.sub.6 is Alk, OAlk, halogen or X; R.sub.7 is H, Alk, OAlk, halogen or Y; R.sub.8 and R.sub.8' are H, Alk, (CH.sub.2).sub.p Ph, (CH.sub.2).sub.p Nph or taken together are --(CH.sub.2).sub.4 -- or --(CH.sub.2).sub.5 --; R.sub.9 is H, Alk or Y; R.sub.10 is H or Alk; R.sub.11 and R.sub.11' are H, C.sub.1-5 alkyl, C.sub.3-7 cycloalkyl, Ar, Ar--C.sub.1-5 alkyl, Ar--C.sub.3-7 cycloalkyl; Ar is phenyl or phenyl substituted by one or two C.sub.1-5 alkyl, trifluoromethyl, hydroxy, C.sub.1-5 alkoxy or halogen groups; n is 1 or 2; q is 0 or 1; and p is 0, 1, 2 or 3; or a pharmaceutically acceptable salt thereof; which are effective for inhibiting platelet aggregation, pharmaceutical compositions for effecting such activity, a method for inhibiting platelet aggregation and clot formation in a mammal, and a method for inhibiting reocclusion of a blood vessel following fibrinolytic therapy.

  这项发明涉及以下式的化合物：##STR1## 其中：A'为不存在，Asn，Gln，Ala或Abu；A不存在或为Arg，HArg，（Me.sub.2）Arg，（Et.sub.2）Arg，Abu，Ala，Gly，His，Lys或其α-R'取代衍生物，Dtc，Tpr和Pro中选择的D-或L-氨基酸；B为Arg，HArg，NArg，（Me.sub.2）Arg，（Et.sub.2）Arg和Lys或其α-R'取代衍生物中选择的D-或L-氨基酸；Q不存在或为Tyr，（Alk）Tyr，Phe，（4'W）Phe，HPhe，Phg，Pro，Trp，His，Ser，（Alk）Ser，Thr，（Alk）Thr，（Alk）Cys，（Alk）Pen，Ala，Val，Nva，Met，Leu，Ile，Nle和Nal或其α-R'取代衍生物中选择的D或L氨基酸；M不存在或为Gly或在n为1时为B-Gly-Glu-Q中选择的D-或L-氨基酸；W为卤素或Alk；R'为Alk或PhCH.sub.2；##STR2## 其中Z.sub.1和Z.sub.2通过L.sup.1和L.sup.2之间的共价键连接；或Z.sub.1和Z.sub.2一起构成氨基末端残基与羧基末端残基之间的共价键；L.sup.1和L.sup.2为--S--或--(CH.sub.2).sub.p--；X为R.sub.4R.sub.5N或H；Y为H，CONR.sub.1R.sub.2或CO.sub.2R.sub.2；R.sub.1和R.sub.2为H，Alk或（CH.sub.2).sub.pAr；R.sub.3和R.sub.3'为H，Alk，（CH.sub.2).sub.pAr或一起为--(CH.sub.2).sub.4--或--(CH.sub.2).sub.5--；R.sub.4为H或Alk；R.sub.5为R.sub.11，R.sub.11CO，R.sub.11OCO，R.sub.11OCH(R.sub.11')CO，R.sub.11NHCH(R.sub.11')CO，R.sub.11SCH(R.sub.11')CO，R.sub.11SO.sub.2或R.sub.11SO；R.sub.6为Alk，OAlk，卤素或X；R.sub.7为H，Alk，OAlk，卤素或Y；R.sub.8和R.sub.8'为H，Alk，（CH.sub.2).sub.pPh，（CH.sub.2).sub.pNph或一起为--(CH.sub.2).sub.4--或--(CH.sub.2).sub.5--；R.sub.9为H，Alk或Y；R.sub.10为H或Alk；R.sub.11和R.sub.11'为H，C.sub.1-5烷基，C.sub.3-7环烷基，Ar，Ar--C.sub.1-5烷基，Ar--C.sub.3-7环烷基；Ar为苯基或被一个或两个C.sub.1-5烷基，三氟甲基，羟基，C.sub.1-5烷氧基或卤素基取代的苯基；n为1或2；q为0或1；p为0，1，2或3；或其药学上可接受的盐；用于抑制血小板聚集的有效化合物，用于实现该活性的药物组合物，用于在哺乳动物中抑制血小板聚集和凝块形成的方法，以及用于防止纤溶疗法后血管再闭塞的方法。
• Asymmetric Synthesis of 2,4,5-Trisubstituted Δ²-Thiazolines
  作者：Christoffer Bengtsson、Hanna Nelander、Fredrik Almqvist

  DOI：10.1002/chem.201301120

  日期：2013.7.22

  AbstractΔ2‐Thiazolines are interesting heterocycles that display a wide variety of biological characteristics. They are also common in chiral ligands used for asymmetric syntheses and as synthetic intermediates. Herein, we present asymmetric routes to 2,4,5‐trisubstituted Δ2‐thiazolines. These Δ2‐thiazolines were synthesized from readily accessible/commercially available α,β‐unsaturated methyl esters through a Sharpless asymmetric dihydroxylation and an O→N acyl migration reaction as key steps. The final products were obtained in good yields with up to 97 % enantiomeric excess.
• US5643872A
  申请人：——

  公开号：US5643872A

  公开（公告）日：1997-07-01
• Enantioselective routes to protected syn- and anti-.beta.-phenylcysteines
  作者：M. Amparo Lago、James Samanen、John D. Elliott

  DOI：10.1021/jo00038a048

  日期：1992.6