Sodium Methoxide → benzyl 2-azido-2,4-dideoxy-4-fluoro-beta-D-mannopyranoside

HRID 1948830Notes

Reaction equation

[N:1]([C@H:4]1[C@@H:17]([O:18]C(=O)C(C)(C)C)[C@H:16]([F:25])[C@@H:15]([CH2:26][O:27]C(=O)C(C)(C)C)[O:14][C@H:5]1[O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[N+:2]=[N-:3].C[O-].[Na+]>CO>[N:1]([C@H:4]1[C@@H:17]([OH:18])[C@H:16]([F:25])[C@@H:15]([CH2:26][OH:27])[O:14][C@H:5]1[O:6][CH2:7][C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)=[N+:2]=[N-:3]

Participants

Conditions

Temperature: 40 °C

Procedure

Compound (22) (180 mg, 0.387 mmol) was dissolved in methanol (8 ml), sodium methoxide (922 mg, 9.67 mmols) was added to the solution, and the mixture was reacted with stirring at 40° C. TLC revealed 4.5 hours later that the reaction mixture collected into a spot, and the mixture was neutralized with a cation-exchange resin IR-120(+), followed by filtration and concentration. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:1), giving Compound (23) (in an amount of 105.3 mg, 91.6% in yield).

Workup

customthe mixture was reacted
customcollected into a spot
filtrationfollowed by filtration and concentration
customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:1)

Sources & evidence

ORD record: ord-4f94f06c38f7497bb76806e0539e2379
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08399656B2

Reaction notes

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