Water → HCID 14584473, compound

HRID 1655998Notes

Reaction equation

[N:1]([C@H:4]([CH2:28][O:29][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C@H:5]1[O:11][CH:8]([O:9]C)[C@H:7]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C@H:6]1[O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[N+:2]=[N-:3].FC(F)(F)C(O)=O.O>O1CCCC1>[N:1]([C@H:4]([CH2:28][O:29][CH2:30][C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1)[C@H:5]1[O:11][CH:8]([OH:9])[C@H:7]([O:12][CH2:13][C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[C@H:6]1[O:20][CH2:21][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)=[N+:2]=[N-:3]

Participants

Conditions

Temperature: -10 °C

Procedure

Methyl 5-azido-2,3,6-tri-O-benzyl-5-deoxy-D-glucofuranoside (10.8 g, 22.2 mmol) was dissolved at room temperature in tetrahydrofuran (20 ml). The solution was cooled at -10° C. and trifluoroacetic acid (120 ml) was added dropwise followed by addition of water (20 ml). The mixture was stirred at 0° C. during 24 h. The mixture was evaporated under reduced pressure without heating. The residue was taken with ether and washed with water. The organic layer was dried over sodium sulfate, filtered and concentrated under reduced pressure. Flash chromatography on silica gel and elution with a 20:80 mixture of ethyl acetate and hexane afforded 5-azido-2,3,6-tri-O-benzyl-5-deoxy-D-glucofuranose as a colorless oil (9.63 g, 90%).

Workup

customThe mixture was evaporated under reduced pressure
temperaturewithout heating
washwashed with water
dry with materialThe organic layer was dried over sodium sulfate
filtrationfiltered
concentrationconcentrated under reduced pressure
washFlash chromatography on silica gel and elution
additionwith a 20:80 mixture of ethyl acetate and hexane

Sources & evidence

ORD record: ord-231fcbaf21254380a34e6615be95e281
Source dataset: uspto-grants-1993_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05252587

Reaction notes

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