(3R,4S,5R,6R)-3,4,5-Tris(benzyloxy)-6-((benzyloxy)methyl)oxan-2-one → HCID 68794922, compound

HRID 1713590Notes

Reaction equation

HRID 1713590 reaction equation
[CH2:1]([O:8][C@@H:9]1[C@@H:14]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C@H:13]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C@@H:12]([CH2:31][O:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[O:11][C:10]1=[O:40])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[C:42]1[CH:47]=[C:46]([CH2:48][C:49]2[CH:54]=[CH:53][C:52]([CH2:55][CH3:56])=[CH:51][CH:50]=2)[C:45]([Cl:57])=[CH:44][C:43]=1[O:58][CH3:59].[Li]CCCC>C1COCC1>[CH2:1]([O:8][C@@H:9]1[C@@H:14]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C@H:13]([O:23][CH2:24][C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[C@@H:12]([CH2:31][O:32][CH2:33][C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)[O:11][C@:10]1([C:42]1[CH:47]=[C:46]([CH2:48][C:49]2[CH:54]=[CH:53][C:52]([CH2:55][CH3:56])=[CH:51][CH:50]=2)[C:45]([Cl:57])=[CH:44][C:43]=1[O:58][CH3:59])[OH:40])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 10907626(3R,4S,5R,6R)-3,4,5-Tris(benzyloxy)-6-((benzyloxy)methyl)oxan-2-oneHCID 462061181-Bromo-4-chloro-5-(4-ethylbenzyl)-2-methoxybenzeneHCID 178418339Butyllithium

Product 1

HCID 68794922HCID 68794922, compoundYield 64.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-one 5 (1.10 g, 2.04 mmol) and 1-bromo-4-chloro-5-(4-ethylbenzyl)-2-methoxybenzene 22 (0.60 g, 1.77 mmol) in anhydrous THF (20 mL) at −78° C. was added a solution of n-BuLi (0.78 mL, 1.94 mmol, 2.5 M). The mixture was stirred for 1 h, warmed to ambient temperature, quenched with 10% sodium carbonate (100 mL), and extracted with ethyl acetate (2×50 mL). The organic phase was dried with anhydrous MgSO4, filtered, and evaporated to dryness. The residue was purified by silica gel column chromatography using 15-25% ethyl acetate in petroleum ether to give 23 (0.91 g, 64%). LC/MS m/z 822 (M+Na), 782 (M−OH).

Workup

  1. customquenched with 10% sodium carbonate (100 mL)
  2. extractionextracted with ethyl acetate (2×50 mL)
  3. dry with materialThe organic phase was dried with anhydrous MgSO4
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-231e43f267f64a75b6a30a29b4de575b
Source dataset
uspto-grants-2010_09
Patent number
US07795228B2

Reaction notes

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