• English
  • 简体中文
Login Register
Current Location: Home > Feedback Help Print

【结 构 式】

【分子编号】58550

【品名】tert-butyl (1S)-1-benzyl-2-({(1R)-3-methyl-1-[(1S,2S,6R,8S)-2,9,9-trimethyl-3,5-dioxa-4-boratricyclo[6.1.1.0~2,6~]dec-4-yl]butyl}amino)-2-oxoethylcarbamate

【CA登记号】

【 分 子 式 】C29H45BN2O5

【 分 子 量 】512.49778

【元素组成】C 67.96% H 8.85% B 2.11% N 5.47% O 15.61%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号:(III)

Pinanediol leucine boronate (I) was coupled with N-Boc-L-phenylalanine (II) in the presence of TBTU to afford the dipeptide boronate (III). Acid cleavage of the Boc protecting group of (III), followed by acylation of the resultant amine (IV) with 2-pyrazinecarboxylic acid (V), furnished amide (VI). Finally, deprotection of the boronic acid (VI) was accomplished by two-phase transesterification with isobutylboronic acid.

1 Adams, J.; Behnke, M.; Chen, S.; Cruickshank, A.A.; Dick, L.R.; Grenier, L.; Klunder, J.M.; Ma, Y.T.; Plamondon, L.; Stein, R.L.; Potent and selective inhibitors of the proteasome: Dipeptidyl boronic acids. Bioorg Med Chem Lett 1998, 8, 4, 333.
2 Adams, J.; Ma, Y.-T.; Stein, R.; Baevsky, M.; Grenier, L.; Plamondon, L. (ProScript, Inc.); Boronic ester and acid cpds., synthesis and uses. JP 1998510245; US 5780454; US 6083903; WO 9613266 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 58549 (1R)-3-methyl-1-[(1S,2S,6R,8S)-2,9,9-trimethyl-3,5-dioxa-4-boratricyclo[6.1.1.02,6]dec-4-yl]-1-butanamine 2,2,2-trifluoroacetate; (1R)-3-methyl-1-[(1S,2S,6R,8S)-2,9,9-trimethyl-3,5-dioxa-4-boratricyclo[6.1.1.02,6]dec-4-yl]butylamine 2,2,2-trifluoroacetate 179324-87-9 C15H28BNO2.CF3COOH 详情 详情
(II) 12874 (2R)-2-[(tert-Butoxycarbonyl)amino]-3-phenylpropionic acid; N-alpha-t-BOC-L-Phenylalanine 13734-34-4 C14H19NO4 详情 详情
(III) 58550 tert-butyl (1S)-1-benzyl-2-({(1R)-3-methyl-1-[(1S,2S,6R,8S)-2,9,9-trimethyl-3,5-dioxa-4-boratricyclo[6.1.1.0~2,6~]dec-4-yl]butyl}amino)-2-oxoethylcarbamate C29H45BN2O5 详情 详情
(IV) 58551 (2S)-2-amino-N-{(1R)-3-methyl-1-[(1S,2S,6R,8S)-2,9,9-trimethyl-3,5-dioxa-4-boratricyclo[6.1.1.0~2,6~]dec-4-yl]butyl}-3-phenylpropanamide C24H37BN2O3 详情 详情
(V) 37256 2-pyrazinecarboxylic acid; Pyrazinoic acid 98-97-5 C5H4N2O2 详情 详情
(VI) 58552 N-[(1S)-1-benzyl-2-({(1R)-3-methyl-1-[(1S,2S,6R,8S)-2,9,9-trimethyl-3,5-dioxa-4-boratricyclo[6.1.1.0~2,6~]dec-4-yl]butyl}amino)-2-oxoethyl]-2-pyrazinecarboxamide C29H39BN4O4 详情 详情
Extended Information