D-N-Boc-nor-leucine methyl ester | 116611-59-7

• 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: D-N-Boc-nor-leucine methyl ester
• 英文别名: methyl (2R)-2-(tert-butoxycarbonylamino)hexanoate；(R)-Methyl 2-((tert-butoxycarbonyl)amino)hexanoate；methyl (2R)-2-[(2-methylpropan-2-yl)oxycarbonylamino]hexanoate
• CAS: 116611-59-7
• 化学式: C₁₂H₂₃NO₄
• 分子量: 245.319
• InChiKey: ROZBCRMGQFLYFJ-SECBINFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  17
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  甲基溴化镁 、 D-N-Boc-nor-leucine methyl ester 以 乙醚 为溶剂， 反应 5.66h， 以3.21 g的产率得到tert-butyl N-[(1R)-1-(1-hydroxy-1-methylethyl)pentyl]carbamate
  参考文献：
  名称：

  [EN] N-1 BRANCHED ALKYL SUBSTITUTED IMIDAZO[4,5-C]QUINOLINE COMPOUNDS, COMPOSITIONS, AND METHODS
  [FR] COMPOSÉS IMIDAZO[4,5-C]QUINOLÉINE SUBSTITUÉS PAR ALKYLE N-1 RAMIFIÉ, COMPOSITIONS ET PROCÉDÉS

  摘要：

  本发明公开了在N-1位置通过支链基团连接的Imidazo[4,5-c]喹啉化合物，化合物的单对映体，含有这些化合物的药物组合物，以及制备这些化合物的方法。还公开了将这些化合物用作免疫应答调节剂的方法，用于诱导（或抑制）人类和动物体内的细胞因子生物合成，并用于治疗包括传染性和肿瘤性疾病在内的疾病的方法。

  公开号：

  WO2020245706A1
• 作为产物：
  描述：

  在 氢氧化钾 、 potassium permanganate 作用下， 以 水 、 叔丁醇 为溶剂， 生成 D-N-Boc-nor-leucine methyl ester
  参考文献：
  名称：

  Chiral electrophilic “glycinal” equivalents. New synthons for optically active α-amino acids and 4-substituted 2-oxazolidinones

  摘要：

  The thermal reaction of 3-[(IS)-2-alkoxy-1-apocamphanecarbonyl]-2-oxazolones (21a-c) with dialkyl azodicarboxylates (9) results in exclusive formation of [4 + 2] type cycloadducts (22 and 23) with moderate levels of diastereofacial selection (up to 72% d.e.). The diastereomers thus obtained were readily purified and subsequent treatment with acidic methanol followed by removal of the auxiliary with LiBH4/MeOH (1:2) gave optically pure 4-methoxy-5-hydrazino-2-oxazolidinones (26 and 27), which serve as alpha-aminoaldehyde templates useful for the synthesis of a wide variety of optically active alpha-amino acids as well as 4-alkyl and 4-aryl-2-oxazolidinones. (C) 1997, Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(96)01077-0

文献信息

• Les organocuprates dans une nouvelle synthese d'aminoacides enantiomeriquement purs
  作者：J.A. Bajgrowicz、A. El Hallaoui、R. Jacquier、Ch. Pigiere、Ph. Viallefont

  DOI：10.1016/s0040-4020(01)96546-9

  日期：1985.1

  A new general method of synthesis of optically pure α- amino esters was elaborated during studies on the reaction of organocuprates with tosyl and halogeno derivatives of L-serine and L-homoserine.

  在研究有机铜酸盐与L-丝氨酸和L-高丝氨酸的甲苯磺酰基和卤代衍生物的反应过程中，阐述了一种合成光学纯的α-氨基酯的新通用方法。
• Lithium diorganocuprate reactions with l-serine derivatives
  作者：J.A. Bajgrowicz、A. El Hallaoui、R. Jacquier、Ch. Pigière、Ph. Viallefont

  DOI：10.1016/s0040-4039(01)81283-1

  日期：——

  The lithium diorganocuprate reactions with L-serine derivatives are studied. Retention of configuration, or at least a high enantiomeric excess (>80%) of the formed α-amino esters is observed in all cases. Attempts are made to restrict side-reactions.

  研究了L-丝氨酸衍生物的二有机十二酸锂反应。在所有情况下都观察到构型的保留，或至少高对映体过量（> 80％）的形成的α-氨基酯。试图限制副反应。
• THROMBIN INHIBITORS
  申请人：——

  公开号：US20010007764A1

  公开（公告）日：2001-07-12

  The invention relates to non-slow-binding thrombin inhibitors of the formula: A-B-C-Lys-D wherein A is H, 2 -hydroxy- 3 -cyclohexyl-propionyl-, R 1 , R 1 —O—CO—, R 1 —SO 2 —, —(CHR 2 ) n COOR 3 , or an N-protecting group, wherein R 1 is selected from -( 1 - 6 C)alkylene-COOH, ( 1 - 12 C)alkenyl, ( 6 - 14 C)aryl, ( 7 - 15 C)aralkyl and ( 8 - 16 C)aralkenyl, the group of which may be substituted with ( 1 - 6 C)alkyl, ( 2 - 12 C)alkoxy, hydroxy, or halogen; R 2 is H or has the same meaning as R 1 , R 3 is selected from H, ( 1 12 C)alkyl, ( 2 - 12 C)alkenyl, ( 6 - 14 C)aryl, ( 7 - 15 C)aralkyl and ( 8 - 16 C)aralkenyl, the aryl group of which may be substituted with ( 1 - 6 C)alkyl, ( 2 - 12 C)alkoxy, hydroxy or halogen; n is an integer of 1 to 3 ; B is a bond, L-Asp or an derivative thereof, Leu,norLeu, -n(benzyl)—CH 2 —CO—, -N( 2 -indane)—CH 2 —CO—, D- 1 Piq, D-Tiq, Atc or a D-amino acid having a hydrophobic aromatic side chain; C is Azt, Pro, Pec, norLeu(cyclo)Gly, an amino acid of one of the formulae -N[( 3 - 8 C)cycloalkyl]—CH—CO—or -N(benzyl)—CH 2 —CO —, D is selected from COOH, tetrazole, oxazole,thiazole and benzothiazole, or A znd C have the aforesaid meaning, B is D-( 3 - 8 C) cycloalkylalanine, and D is tetrazole, oxazole, thiazole or benzothiazole; or a prodrug thereof; or a pharmaceutically acceptable salt thereof; with the exception of the compound Me-D-Phe-Pro-Lys-COOH. The compounds can be used as antithrombotic agents.

  本发明涉及公式为：A-B-C-Lys-D的非缓慢结合凝血酶抑制剂，其中A为H，2-羟基-3-环己基-丙酰基，R1，R1-O-CO-，R1-SO2-，-(CHR2)nCOOR3或N-保护基，其中R1选自-(1-6C)烷基-COOH，(1-12C)烯基，(6-14C)芳基，(7-15C)芳基烷基和(8-16C)芳基烯基，该基团可以被(1-6C)烷基，(2-12C)烷氧基，羟基或卤素取代；R2为H或具有与R1相同的含义，R3选自H，(112C)烷基，(2-12C)烯基，(6-14C)芳基，(7-15C)芳基烷基和(8-16C)芳基烯基，其中芳基基团可以被(1-6C)烷基，(2-12C)烷氧基，羟基或卤素取代；n是1到3的整数；B是键，L-Asp或其衍生物，Leu，norLeu，-n(benzyl)-CH2-CO-，-N(2-茚烷)- -CO-，D-1Piq，D-Tiq，Atc或具有疏水芳香侧链的D-氨基酸；C是Azt，Pro，Pec，norLeu(cyclo)Gly，其中一种氨基酸的化学式为-N[(3-8C)环烷基]-CH-CO-或-N(benzyl)- -CO-，D选自COOH，四唑，噁唑，噻唑和苯并噻唑，或A和C具有上述含义，B为D-(3-8C)环烷基丙氨酸，D为四唑，噁唑，噻唑或苯并噻唑；或其前药；或其药学上可接受的盐；但不包括化合物Me-D-Phe-Pro-Lys-COOH。这些化合物可用作抗血栓剂。
• Endothelin antagonistic substance
  申请人：Banyu Pharmaceutical Co., Ltd.

  公开号：US05614498A1

  公开（公告）日：1997-03-25

  Peptides having the formula: ##STR1## inhibit the binding of endothelin to its ET.sub.B receptor and are useful in treating diseases associated with excess production or secretion of endothelin.

  具有以下公式的多肽：##STR1## 抑制内皮素与其ET.sub.B受体的结合，可用于治疗与内皮素过度产生或分泌相关的疾病。
• Thrombin inhibitors
  申请人：——

  公开号：US20020142967A1

  公开（公告）日：2002-10-03

  The invention relates to non-slow-binding thrombin inhibitors of the formula: A—B—C-Lys-D— wherein A is H, 2-hydroxy-3-cyclohexyl-proprionyl-, R 1 , R 1 —O—CO—, R 1 —SO 2 —, —(CHR 2 ) n COOR 3 , or an N-protecting group, wherein R 1 is selected from -(1-6C)alkylene-COOH, (1-12C)alkyl, (2-12C)alkenyl, (6-14C)aryl, (7-15C)aralkyl and (8-16C)aralkenyl, the aryl group of which may be substituted with (1-6C)alkyl, (2-12C)alkoxy, hydroxy, or halogen; R 2 is H or has the same meaning as R 1 , R 3 is selected from H, (1-12C)alkyl, (2-12C)alkenyl, (6-14C)aryl, (7-15C)aralkyl and (8-16C)aralkenyl, the aryl group of which may be substitute with (1-6C)alkyl, (2-12C)alkoxy, hydroxy or halogen; n is an integer of 1 to 3; B is a bond, L-asp or an ester derivative thereof, Leu, norLeu, —N(benzyl)-CH 2 —CO—, —N(2-indane)-CH 2 —CO—, D-1 Piq, D-3 Piq, D-Tiq, Atc or a D-amino acid having a hydrophobic aromatic side chain; C is Azt, Pro, Pec, norLeu(cyclo)Gly, an amino acid of one of the formulae —N[(3-8C)cycloalkyl]-CH 2 —CO— or —N(benzol)-CH 2 —CO—, D is selected from COOH, tetrazole, oxazole, thiazole and benxothiazole; or a prodrug thereof; or a pharmaceutically acceptable salt thereof, with the exception of the compound Me-D-Phe-Pro-Lys-COOH. The compounds can be used as antithrombotic agents

  该发明涉及式为：A-B-C-Lys-D-的非缓慢结合血凝酶抑制剂，其中A为H，2-羟基-3-环己基-丙酰基，R1，R1-O-CO-，R1-SO2-，-(CHR2)nCOOR3，或N-保护基，其中R1选自-(1-6C)烷基-COOH，(1-12C)烷基，(2-12C)烯基，(6-14C)芳基，(7-15C)芳基烷基和(8-16C)芳基烯基，其芳基基团可以被(1-6C)烷基，(2-12C)烷氧基，羟基或卤素取代；R2为H或与R1相同，R3选自H，(1-12C)烷基，(2-12C)烯基，(6-14C)芳基，(7-15C)芳基烷基和(8-16C)芳基烯基，其芳基基团可以被(1-6C)烷基，(2-12C)烷氧基，羟基或卤素取代；n为1到3的整数；B为键，L-天门冬氨酸或其酯衍生物，亮氨酸，norLeu，-N(苄基)-CH2-CO-，-N(2-茚烷基)- -CO-，D-1 Piq，D-3 Piq，D-Tiq，Atc或具有疏水性芳香侧链的D-氨基酸；C为Azt，Pro，Pec，norLeu（环）Gly，式为-N[(3-8C)环烷基]- -CO-或-N(苯) -CO-的氨基酸，D选自COOH，四唑，噁唑，噻唑和苯并噻唑；或其前药；或其药学上可接受的盐，但不包括化合物Me-D-Phe-Pro-Lys-COOH。这些化合物可用作抗血栓剂。