Tetrahydrofuran → (1R,2S,3R,4R,5S,6R)-4-(4-chloro-2-(4-ethylbenzyl)phenoxy)-6-(hydroxymethyl)cyclohexane-1,2,3,5-tetraol

HRID 1092439Notes

Reaction equation

HRID 1092439 reaction equation
C1COCC1.C([O:13][C@H:14]1[C@H:19]([O:20]CC2C=CC=CC=2)[C@@H:18]([O:28]CC2C=CC=CC=2)[C@H:17]([O:36][C:37]2[CH:42]=[CH:41][C:40]([Cl:43])=[CH:39][C:38]=2[CH2:44][C:45]2[CH:50]=[CH:49][C:48]([CH2:51][CH3:52])=[CH:47][CH:46]=2)[C@@H:16]([OH:53])[C@@H:15]1[CH2:54][O:55]CC1C=CC=CC=1)C1C=CC=CC=1>[Pd].CO>[Cl:43][C:40]1[CH:41]=[CH:42][C:37]([O:36][C@@H:17]2[C@@H:16]([OH:53])[C@H:15]([CH2:54][OH:55])[C@@H:14]([OH:13])[C@H:19]([OH:20])[C@H:18]2[OH:28])=[C:38]([CH2:44][C:45]2[CH:46]=[CH:47][C:48]([CH2:51][CH3:52])=[CH:49][CH:50]=2)[CH:39]=1

Participants

5

Reactant 2

HCID 8028TetrahydrofuranHCID 57741118(1S,2S,3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-2-(benzyloxymethyl)-6-(4-chloro-2-(4-ethylbenzyl)phenoxy)cyclohexanol

Product 1

HCID 57741100(1R,2S,3R,4R,5S,6R)-4-(4-chloro-2-(4-ethylbenzyl)phenoxy)-6-(hydroxymethyl)cyclohexane-1,2,3,5-tetraolYield 84.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

14 mL of THF and methanol (1:1) was added to the flask containing the (1S,2S,3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-2-(benzyloxymethyl)-6-(4-chloro-2-(4-ethylbenzyl)phenoxy)cyclohexanol (28, 55 mg, 0.070 mmol). 55 mg of Pd/C (10%) was added in one portion to the reaction mixture. The mixture was degassed five times with H2 and the resulting suspension was stirred under an atmosphere of H2 for 3 h at ambient temperature. The reaction mixture was filtered and concentrated, and the residue was purified by preparative LC-MS to obtain 25 mg of (1R,2S,3R,4R,5S,6R)-4-(4-chloro-2-(4-ethylbenzyl)phenoxy)-6-(hydroxymethyl)cyclohexane-1,2,3,5-tetraol (29). 1H-NMR (D2O): δ 7.22˜7.2 (1H, d, J=9.2 Hz), 7.17˜7.11 (4H, q), 7.08˜7.06 (1H, dd), 6.92˜6.91 (1H, d, J=3.2 Hz), 4.11˜4.08 (1H, t J=9.2 Hz), 4.01 (2H, s), 3.92˜3.91 (2H, m), 3.69˜3.665 (1H, dd, J=10.8, 8.8 Hz), 3.46˜3.39 (2H, m), 3.35˜3.30 (1H, m), 2.66˜2.58 (2H, q), 1.52˜1.46 (1H, tt), 1.24˜1.19 (3H, t).

Workup

  1. customThe mixture was degassed five times with H2
  2. filtrationThe reaction mixture was filtered
  3. concentrationconcentrated
  4. customthe residue was purified by preparative LC-MS

Sources & evidence

ORD record
ord-25fbfac66bd34efeaa303147cf3d3d32
Source dataset
uspto-grants-2012_03
Patent number
US08129434B2

Reaction notes

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