Sodium borohydride → 4-O-benzyl-N-benzyloxycarbonyl-1,5-imino-1,2,5-trideoxy-D-arabino-hexitol

HRID 2050675노트

반응식

HRID 2050675 반응식
[CH2:1]([O:8][C@H:9]1[C@H:16]([OH:17])[CH2:15][CH2:14][N:13]([C:18]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[O:19])[C@@H:10]1[CH:11]=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+]>>[CH2:1]([O:8][C@@H:9]1[C@@H:10]([CH2:11][OH:12])[N:13]([C:18]([O:20][CH2:21][C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)=[O:19])[CH2:14][CH2:15][C@H:16]1[OH:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

3

반응물 2

HCID 4311764Sodium borohydrideHCID 1317168873-O-benzyl-N-benzyloxycarbonyl-2,6-imino-2,5,6-trideoxy-D-lyxo-hexose

생성물 1

HCID 145234464-O-benzyl-N-benzyloxycarbonyl-1,5-imino-1,2,5-trideoxy-D-arabino-hexitol

실험 절차

reducing the lactol (24) with sodium borohydride to give a diol (25) from which the protecting groups are removed by hydrogenolysis to give the desired fagomine (3) ##STR17## wherein Bn=CH2Ph and Z=COOCH2Ph.

출처 및 근거

ORD 기록
ord-698a32f3e99f4371bafef8442e45d2de
출처 데이터셋
uspto-grants-1991_05
특허 번호
US05013842

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