Potassium Sodium Tartrate → HCID 68792359, compound

HRID 1713580Notes

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([CH2:42][C:43](OC)=[O:44])[O:40][CH3:41])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(C[AlH]CC(C)C)C.[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+]>C1COCC1.C1(C)C=CC=CC=1>[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:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[O:11][C@:10]1([CH2:42][CH2:43][OH:44])[O:40][CH3:41])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Methyl 2-((2S,3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-2-methoxytetrahydro-2H-pyran-2-yl)acetate (7) (0.48 g, 0.77 mmol) was dissolved in THF (8 mL) under an atmosphere of Ar and cooled to 0° C. DIBAL-H (2 mL of a 20% solution in toluene) was added dropwise. The reaction mixture was stirred at room temperature for 0.75 h, then cooled again to 0° C. and stirred with Rochelle's salt for 2 hours. The mixture was extracted with Et2O (3×). The organic layers were combined, washed with H2O (1×), dried (Na2SO4) and concentrated to a syrup (0.46 g, 100%). LC/MS 98.5% (ELSD) tR=3.10 min, calcd for C37H42O7: 598.29, found 621.3 (M+Na)+.

Workup

temperaturecooled again to 0° C.
extractionThe mixture was extracted with Et2O (3×)
washwashed with H2O (1×)
dry with materialdried (Na2SO4)
concentrationconcentrated to a syrup (0.46 g, 100%)

Sources & evidence

ORD record: ord-0bbb66e982b3440daae4ded21b6fb4b5
Source dataset: uspto-grants-2010_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07795228B2

Reaction notes

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