Diethyl Ether → Nalpha-(3-(beta-D-Galactopyranosyl)cyclohept-1-yl)-L-leucine
Reaction equation
C([O:9][C@@H:10]1[C@@H:24]([O:25]C(=O)C2C=CC=CC=2)[C@@H:23]([O:34]C(=O)C2C=CC=CC=2)[C@@H:22]([CH2:43][O:44]C(=O)C2C=CC=CC=2)[O:21][C@H:11]1OC1CCCCC(=O)C1)(=O)C1C=CC=CC=1.ClC(Cl)(Cl)C(=N)O[C@@H]1O[C@H](COC(=O)C2C=CC=CC=2)[C@H](OC(=O)C2C=CC=CC=2)[C@H](OC(=O)C2C=CC=CC=2)[C@H]1O[C:60](=O)[C:61]1[CH:66]=CC=C[CH:62]=1.O[CH:104]1[CH2:110][CH2:109][CH2:108][CH2:107]C(=O)C1.C1(=[O:119])CCCCC=C1.C([N:122]([CH2:125][CH3:126])CC)C.C([O:129][CH2:130][CH3:131])C>>[C@@H:11]1([CH:110]2[CH2:109][CH2:108][CH2:107][CH2:126][CH:125]([NH:122][C@H:131]([C:130]([OH:129])=[O:119])[CH2:60][CH:61]([CH3:66])[CH3:62])[CH2:104]2)[O:21][C@H:22]([CH2:43][OH:44])[C@H:23]([OH:34])[C@H:24]([OH:25])[C@H:10]1[OH:9]Participants
7
Reactant 6
Product 1
Procedure
Step A--Synthesis of Cycloheptan-1-on-3-yl 2,3,4,6-Tetra-O-benzoyl-β-D-galactopyranoside: O-(2,3,4,6-tetra-O-benzoyl-β-galactopyranosyl) trichloroacetimidate (578 mg, 780 μmol) and 3-hydroxycycloheptan-1-one (100 mg, 780 μmol) (which was prepared in two steps from cyclohept-2-en-1-one by the procedures of E. Hasegawa8 and H. Paulson9 were dissolved in dry diethyl ether (10 mL). Trimethyl trifluoromethanesulfonate (TMSOTf) (300 μmL, 0.1M) is added at room temperature. After 1 h, the reaction is quenched with triethylamine (100 μmol) and the mixture is concentrated. Column chromatography (SiO2, toluene/ethyl acetate 16:1 to 10:1) gives the title compound (385 mg, 70%) as a white foam.
Workup
- concentrationthe mixture is concentrated
Sources & evidence
- ORD record
- ord-cb0c2e1aa1eb4425ac751949efea2da1
- Source dataset
- uspto-grants-1999_08
- Patent number
- US05932554
Reaction notes
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