Hydrogen Peroxide → (1S,2S,3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-2-(benzyloxymethyl)-6-(4-chloro-2-(4-ethylbenzyl)phenoxy)cyclohexanol

HRID 1092438Notes

Reaction equation

HRID 1092438 reaction equation
[CH2:1]([O:8][CH2:9][C:10]1[C@@H:11]([O:49][CH2:50][C:51]2[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=2)[C@H:12]([O:41][CH2:42][C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)[C@@H:13]([O:33][CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[C@H:14]([O:16][C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][C:18]=2[CH2:24][C:25]2[CH:30]=[CH:29][C:28]([CH2:31][CH3:32])=[CH:27][CH:26]=2)[CH:15]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH:57]O.[OH-].[Na+]>C1COCC1>[CH2:50]([O:49][C@H:11]1[C@H:12]([O:41][CH2:42][C:43]2[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=2)[C@@H:13]([O:33][CH2:34][C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=2)[C@H:14]([O:16][C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][C:18]=2[CH2:24][C:25]2[CH:30]=[CH:29][C:28]([CH2:31][CH3:32])=[CH:27][CH:26]=2)[C@@H:15]([OH:57])[C@@H:10]1[CH2:9][O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:51]1[CH:52]=[CH:53][CH:54]=[CH:55][CH:56]=1

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 57741117((1S,2S,3R,6R)-4-(benzyloxymethyl)-6-(4-chloro-2-(4-ethylbenzyl)phenoxy)cyclohex-4-ene-1,2,3-triyl)tris(oxy)tris(methylene)tribenzene

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred 0° C. THF solution of ((1S,2S,3R,6R)-4-(benzyloxymethyl)-6-(4-chloro-2-(4-ethylbenzyl)phenoxy)cyclohex-4-ene-1,2,3-triyl)tris(oxy)tris(methylene)tribenzene (27, 150 mg, 0.196 mmol) was added dropwise BH3OEt2 (2M, 0.98 mL, 1.962 mmol). After stirring for 2 h at 0° C., the mixture was warmed to 25° C. and stirred overnight. H2O2 (30%, 4.2 mL) was added, followed by added aqueous NaOH solution (1M, 3.93 mL, 3.93 mmol) to the reaction mixture at 0° C. After complete addition, the reaction mixture was warmed to 25° C. and stirred for 3 h. The reaction was quenched by addition of dilute HCl (1N, 10 mL) and extracted with ethyl acetate (3×30 mL). The organic layers were washed with water and brine prior to drying over anhydrous Na2SO4. The residue was purified by preparative TLC (EA:PE=1:8 v/v) to obtain 59 mg of (1S,2S,3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-2-(benzyloxymethyl)-6-(4-chloro-2-(4-ethylbenzyl)phenoxy)cyclohexanol (28).

Workup

  1. customTo a stirred 0° C
  2. temperaturethe mixture was warmed to 25° C.
  3. stirringstirred overnight
  4. additionAfter complete addition
  5. temperaturethe reaction mixture was warmed to 25° C.
  6. stirringstirred for 3 h
  7. customThe reaction was quenched by addition of dilute HCl (1N, 10 mL)
  8. extractionextracted with ethyl acetate (3×30 mL)
  9. washThe organic layers were washed with water and brine
  10. dry with materialto drying over anhydrous Na2SO4
  11. customThe residue was purified by preparative TLC (EA:PE=1:8 v/v)

Sources & evidence

ORD record
ord-59a5452ffdba466494a8ac4a7752a089
Source dataset
uspto-grants-2012_03
Patent number
US08129434B2

Reaction notes

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