Methyl Acetate → HCID 68793427, compound

HRID 1713578Notes

Reaction equation

HRID 1713578 reaction equation
[C:1]([O:4][CH3:5])(=[O:3])[CH3:2].CC(C)=O.C(=O)=O.[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[CH2:23]([O:30][C@@H:31]1[C@@H:36]([O:37][CH2:38][C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[C@H:35]([O:45][CH2:46][C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)[C@@H:34]([CH2:53][O:54][CH2:55][C:56]2[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=2)[O:33][C:32]1=[O:62])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>C1COCC1>[CH2:23]([O:30][C@@H:31]1[C@@H:36]([O:37][CH2:38][C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[C@H:35]([O:45][CH2:46][C:47]2[CH:48]=[CH:49][CH:50]=[CH:51][CH:52]=2)[C@@H:34]([CH2:53][O:54][CH2:55][C:56]2[CH:57]=[CH:58][CH:59]=[CH:60][CH:61]=2)[O:33][C@:32]1([CH2:2][C:1]([O:4][CH3:5])=[O:3])[OH:62])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

6

Reactant 4

HCID 6584Methyl AcetateHCID 2733832Lithium HexamethyldisilazideHCID 10907626(3R,4S,5R,6R)-3,4,5-Tris(benzyloxy)-6-((benzyloxy)methyl)oxan-2-oneHCID 18522661Acetone cardice

Product 1

HCID 68793427HCID 68793427, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Methyl acetate (0.25 mL, 3.2 mmol) was dissolved in THF (3 mL) under an atmosphere of Ar and cooled to −78° C. (acetone/dry ice). A solution of LHMDS (3.13 mL, 1M/THF) was added dropwise. After 15 minutes, a solution of (3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-one (5, 1.35 g, 2.5 mmol) in THF (7 mL) was added dropwise. After 3 hr, the reaction mixture was quenched with NH4Cl (aq), warmed to room temperature and extracted with EtOAc (1×). The organic layer was washed with brine (1×), dried (Na2SO4), and concentrated to a syrup (1.4 g, 92%). 1H NMR (300 MHz, CDCl3) δ ppm: 7.15-7.31 (m, 20H), 2.26 (d, J=1.5 Hz, 1H), 4.81-4.97 (m, 4H), 4.45-4.66 (m, 4H), 3.98 (m, 1H), 3.58-3.75 (m, 7H), 3.31 (dd, J=9.6, 1.5 Hz, 1H), 2.73 (d, J=15.6 Hz, 1H), 2.30 (d, J=15.6 Hz, 1H). LC/MS tR=3.16 min, calcd for C37H40O8: 612.27, found 635.6 (M+Na)+.

Workup

  1. waitAfter 3 hr
  2. customthe reaction mixture was quenched with NH4Cl (aq)
  3. extractionextracted with EtOAc (1×)
  4. washThe organic layer was washed with brine (1×)
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated to a syrup (1.4 g, 92%)

Sources & evidence

ORD record
ord-7882bc2e63f14a8781e63b3d0fbd71ff
Source dataset
uspto-grants-2010_09
Patent number
US07795228B2

Reaction notes

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