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Sodium cyanoborohydride → Nalpha-(3-(beta-D-Galactopyranosyl)cyclohept-1-yl)-L-leucine

HRID 1584680
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HRID 1584680 반응식
C([O:5][C:6](=[O:63])[C@H:7]([CH2:59][CH:60]([CH3:62])[CH3:61])[NH:8][CH:9]1[CH2:15][CH2:14][CH2:13][CH2:12][CH:11]([C@@H:16]2[O:48][C@H:47]([CH2:49][O:50]C(=O)C3C=CC=CC=3)[C@H:37]([O:38]C(=O)C3C=CC=CC=3)[C@H:27]([O:28]C(=O)C3C=CC=CC=3)[C@H:17]2[O:18]C(=O)C2C=CC=CC=2)[CH2:10]1)(C)(C)C.Cl.Cl.C(OC(=O)[C@H](CC(C)C)N)(C)(C)C.C([BH3-])#N.[Na+]>ClCCl.CO>[C@@H:16]1([CH:11]2[CH2:12][CH2:13][CH2:14][CH2:15][CH:9]([NH:8][C@H:7]([C:6]([OH:63])=[O:5])[CH2:59][CH:60]([CH3:61])[CH3:62])[CH2:10]2)[O:48][C@H:47]([CH2:49][OH:50])[C@H:37]([OH:38])[C@H:27]([OH:28])[C@H:17]1[OH:18]
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참가 물질

6

반응물 3

HCID 5003444Sodium cyanoborohydrideHCID 53762226Nalpha-(3-(2,3,4,6-Tetra-O-benzoyl-beta-D-galactopyranosyl)cyclohept-1-yl)-L-leucine tert-Butyl EsterHCID 86754378L-leucine tert-butyl ester dihydrochloride

생성물 1

HCID 54317719Nalpha-(3-(beta-D-Galactopyranosyl)cyclohept-1-yl)-L-leucine수율 78%

시약·촉매·용매 2

HCID 887
Methanol
용매
HCID 6344Dichloromethane용매

실험 절차

Step B--Synthesis of Nα-(3-(2,3,4,6-Tetra-O-benzoyl-β-D-galactopyranosyl)cyclohept-1-yl)-L-leucine tert-Butyl Ester: To the product from Step A (50 mg, 71 μmol) and L-leucine tert-butyl ester dihydrochloride (80 mg, 354 μmol) in dichloromethane (700 μL) and methanol 700 μL) was added sodium cyanoborohydride (2 mg). After 48 h, the mixture was concentrated and purified by column chromatography (SiO2, toluene/ethyl acetate, 8:1) to give the title compound (48 mg, 78%).

후처리

  1. concentrationthe mixture was concentrated
  2. custompurified by column chromatography (SiO2, toluene/ethyl acetate, 8:1)

출처 및 근거

ORD 기록
ord-e55e3a22e8094742bba0e37517321564
출처 데이터셋
uspto-grants-1999_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05932554

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