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

HRID 1584680Notes

Reaction equation

HRID 1584680 reaction equation
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]

Participants

6

Reactant 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

Product 1

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

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

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%).

Workup

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

Sources & evidence

ORD record
ord-e55e3a22e8094742bba0e37517321564
Source dataset
uspto-grants-1999_08
Patent number
US05932554

Reaction notes

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