(Diethylamino)sulfur trifluoride → Benzyl 2-O-chloroacetyl-4-deoxy-4-fluoro-3,6-di-O-pivaloyl-beta-D-glucopyranoside

HRID 560960Notes

Reaction equation

[Cl:1][CH2:2][C:3]([O:5][C@@H:6]1[C@@H:19]([O:20][C:21](=[O:26])[C:22]([CH3:25])([CH3:24])[CH3:23])[C@@H:18](O)[C@@H:17]([CH2:28][O:29][C:30](=[O:35])[C:31]([CH3:34])([CH3:33])[CH3:32])[O:16][C@H:7]1[O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:4].CCN(S(F)(F)[F:42])CC>ClCCl>[Cl:1][CH2:2][C:3]([O:5][C@@H:6]1[C@@H:19]([O:20][C:21](=[O:26])[C:22]([CH3:25])([CH3:24])[CH3:23])[C@H:18]([F:42])[C@@H:17]([CH2:28][O:29][C:30](=[O:35])[C:31]([CH3:34])([CH3:33])[CH3:32])[O:16][C@H:7]1[O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:4]

Participants

Conditions

Temperature: -15 °C

Procedure

Compound (19) (300 mg, 0.583 mmol) was dissolved in dichloromethane (5.8 ml), and diethylaminosulfatrifluoride (DAST) was added to the solution with stirring under an argon stream at −15° C. The mixture was returned to room temperature 10 minutes after the addition of DAST and reacted for 1 hour. Disappearance of the material was confirmed by TLC, the DAST was quenched with methanol (3 ml), and the reaction mixture was concentrated in a vacuum. The residue was purified by silica gel chromatography (ethyl acetate:hexane=1:6), giving Compound (20) (in an amount of 211 mg, yield 70%).

Workup

customreacted for 1 hour
customthe DAST was quenched with methanol (3 ml)
concentrationthe reaction mixture was concentrated in a vacuum
customThe residue was purified by silica gel chromatography (ethyl acetate:hexane=1:6)

Sources & evidence

ORD record: ord-6d88e17d12624c82a04cd111e7f358d0
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08063202B2

Reaction notes

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