4-Hydroxybenzaldehyde → 4-(2,3,4,6-Tetra-O-acetyl-D-glucopyranosyloxy)benzaldehyde

HRID 633770Notes

Reaction equation

Cl[C:2](Cl)(Cl)[C:3](=N)[O:4][C@H:5]1[O:22][C@H:21]([CH2:23][O:24][C:25](=[O:27])[CH3:26])[C@H:16]([O:17][C:18](=[O:20])[CH3:19])[C@H:11]([O:12][C:13](=[O:15])[CH3:14])[C@H:6]1[O:7][C:8](=[O:10])[CH3:9].OC1C=[CH:38][C:35]([CH:36]=[O:37])=[CH:34][CH:33]=1.B(F)(F)F.CCOCC.C([O-])(O)=O.[Na+]>C(Cl)Cl>[C:8]([O:7][C@@H:6]1[C@@H:11]([O:12][C:13](=[O:15])[CH3:14])[C@H:16]([O:17][C:18](=[O:20])[CH3:19])[C@@H:21]([CH2:23][O:24][C:25](=[O:27])[CH3:26])[O:22][CH:5]1[O:4][C:3]1[CH:33]=[CH:34][C:35]([CH:36]=[O:37])=[CH:38][CH:2]=1)(=[O:10])[CH3:9]

Participants

Conditions

Temperature: -20 °C

Procedure

2,3,4,6-Tetra-O-acetyl-α-D-galactopyranosyl 2,2,2-trichloroacetimidate 1 (9.85 g, 20 mmol) and 4-hydroxybenzaldehyde (3.66 g, 30 mmol) were dissolved in CH2Cl2 (100 mL) and then the reaction mixture was cooled to −20° C. Boron trifluoride diethyl etherate (46%, 16 mL, 60 mmol) was added dropwise at this temperature. The reaction mixture was stirred at −20° C. for 4 h and was monitored by TLC. Saturated NaHCO3 aqueous solution (150 mL) was added to the mixture. The aqueous layer was separated and extracted with CH2Cl2 (2×150 mL). The organic layers were combined, dried over MgSO4 and concentrated. Purification by silica gel column chromatography yielded 2 (3.8 g, 42%) as a white solid.

Workup

customThe aqueous layer was separated
extractionextracted with CH2Cl2 (2×150 mL)
dry with materialdried over MgSO4
concentrationconcentrated
customPurification by silica gel column chromatography

Sources & evidence

ORD record: ord-bc58c8aa9a654807a81cd70ad6ad8d1d
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09321795B2

Reaction notes

Loading…