SYNTHETIC STUDIES OF CARBAPENEM AND PENEM ANTIBIOTICS .3. A SYNTHESIS OF A KEY INTERMEDIATE FOR 1-BETA-METHYLCARBAPENEM

被引:0
|
作者
SASAKI, A [1 ]
MATSUMURA, H [1 ]
YANO, T [1 ]
TAKATA, S [1 ]
SUNAGAWA, M [1 ]
机构
[1] SUMITOMO PHARMACEUT CO LTD, RES LABS, 3-1-98 KASUGADE NAKA, KONOHANA KU, OSAKA 554, JAPAN
关键词
1-ALPHA-METHYLCARBAPENEM; 1-BETA-METHYLCARBAPENEM; (3S; 4S)-4-[(R)-1-CARBOXYETHYL]-3-[(R)-1-HYDROXYETHYL]-2-AZETIDINONE; STEREOSELECTIVE HYDROGENATION; STEREOSELECTIVE HYDROBORATION;
D O I
暂无
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
We synthesized useful intermediates 5 and 6 for 1-beta- and 1-alpha-methylcarbapenems from 4-carboxy-3-[(R)-1-hydroxyethyl]-2-azetidinone 4 as a starting material by using stereoselective hydrogenation and hydroboration, respectively. A practical synthetic route from 4 to the (3S,4S)4-[(R)-1-carboxyethyl]-3-[(R)-1-hydroxyethyl]-2-azetidinone derivative 1, a useful intermediate for the synthesis of 1-beta-methylcarbapenem antibiotics, was established.
引用
收藏
页码:1098 / 1104
页数:7
相关论文
共 50 条
  • [41] SYNTHETIC CARBAPENEM ANTIBIOTICS .3. 1-METHYL THIENAMYCIN
    SHIH, DH
    CAMA, L
    CHRISTENSEN, BG
    TETRAHEDRON LETTERS, 1985, 26 (05) : 587 - 590
  • [42] DIASTEREOSELECTIVE ROUTES TO A 1-BETA-METHYLCARBAPENEM KEY INTERMEDIATE - SCOPE OF ATE COMPLEX-FORMATION BETWEEN ESTER ENOLATES AND ORGANOBORANES AND ORGANOALANES
    BENDER, DR
    DEMARCO, AM
    MELILLO, DG
    RISEMAN, SM
    SHINKAI, I
    JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (08): : 2411 - 2418
  • [43] COMPOUND SEPARATION BY CYCLIC, SELECTIVE DISSOLUTION - ISOLATION OF DIASTEREOMERIC, 1-BETA-METHYLCARBAPENEM KEY INTERMEDIATES
    BENDER, DR
    DEMARCO, AM
    MCCAULEY, JA
    SEPARATION SCIENCE AND TECHNOLOGY, 1993, 28 (05) : 1169 - 1176
  • [44] Novel synthetic route of a pivotal intermediate for the synthesis of 1β-methyl carbapenem antibiotics
    YuO, Yuan
    Zhou, Wu-Chun
    Zhang, Ji
    Zhang, Mei
    Xu, Da-Yong
    Tang, Yun
    Li, Bo-Gang
    Yu, Xiao-Qi
    ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2006, 10 (04) : 829 - 832
  • [45] FORMAL TOTAL SYNTHESIS OF 1-BETA-METHYLCARBAPENEM VIA A NOVEL ROUTE TO DEOXYAMINO SUGARS
    UDODONG, UE
    FRASERREID, B
    JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (09): : 2103 - 2112
  • [46] SYNTHESIS AND ANTIBACTERIAL ACTIVITY OF FR21818, A NEW, POTENT 1-BETA-METHYLCARBAPENEM
    AZAMI, H
    BARRETT, D
    TANAKA, A
    SASAKI, H
    MATSUDA, K
    CHIBA, T
    MATSUMOTO, Y
    MATSUMOTO, S
    MORINAGA, C
    ISHIGURO, K
    TAWARA, S
    SAKANE, K
    TAKASUGI, H
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1995, 5 (19) : 2199 - 2202
  • [47] NITRONE CYCLOADDITION ROUTE TO THE 1 BETA-METHYLCARBAPENEM KEY INTERMEDIATE
    ITO, Y
    KIMURA, Y
    TERASHIMA, S
    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1987, 60 (09) : 3337 - 3340
  • [48] HIGHLY STEREOCONTROLLED SYNTHESIS OF THE 1-BETA-METHYLCARBAPENEM KEY INTERMEDIATE BY THE REFORMATSKY REACTION OF 3-(2-BROMOPROPIONYL)-2-OXAZOLIDONE DERIVATIVES WITH A 4-ACETOXY-2-AZETIDINONE
    ITO, Y
    SASAKI, A
    TAMOTO, K
    SUNAGAWA, M
    TERASHIMA, S
    TETRAHEDRON, 1991, 47 (16-17) : 2801 - 2820
  • [49] SYNTHETIC STUDIES OF CARBAPENEM AND PENEM ANTIBIOTICS .4. STEREOSELECTIVE REDUCTION OF 3-ACETYL-2-AZETIDINONE WITH AMINOALKOXYBORANE
    SUNAGAWA, M
    YANO, T
    TAKATA, S
    INOUE, T
    SASAKI, A
    MATSUMURA, H
    CHEMICAL & PHARMACEUTICAL BULLETIN, 1992, 40 (11) : 3076 - 3078
  • [50] A NOVEL SYNTHESIS OF THE 1-BETA-METHYLCARBAPENEM KEY INTERMEDIATE EMPLOYING THE [2+2]-CYCLOADDITION REACTION OF CHLOROSULFONYL ISOCYANATE WITH A 4H-1,3-DIOXIN DERIVATIVE
    ITO, Y
    KOBAYASHI, Y
    TERASHIMA, S
    TETRAHEDRON LETTERS, 1989, 30 (41) : 5631 - 5634