Sodium → HCID 12114344, compound

HRID 967339Notes

Reaction equation

[Na].[N:2]([C@@H:5]1[C@@H:12]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=2)[C@H:11]([O:23]C(C2C(C3C=CC=CC=3)=CC=CC=2)=O)[C@@H:10]([CH2:38][O:39][Si:40]([C:53]([CH3:56])([CH3:55])[CH3:54])([C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)[C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[O:9][C@H:6]1[S:7][CH3:8])=[N+:3]=[N-:4]>CO.C1COCC1>[N:2]([C@@H:5]1[C@@H:12]([O:13][CH2:14][C:15]2[CH:16]=[CH:17][C:18]([O:21][CH3:22])=[CH:19][CH:20]=2)[C@H:11]([OH:23])[C@@H:10]([CH2:38][O:39][Si:40]([C:53]([CH3:56])([CH3:55])[CH3:54])([C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)[C:41]2[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=2)[O:9][C@H:6]1[S:7][CH3:8])=[N+:3]=[N-:4]

Participants

Conditions

Temperature: 40 °C

Procedure

Sodium (89 mg) was reacted in dry MeOH (50 mL) then a solution of methyl 2-azido-4-O-biphenylcarbonyl-6-O-tert-butyldiphenylsilyl-2-deoxy-3-O-(4-methoxybenzyl)-1-thio-β-D-glucopyranoside (11) (3 g, 3.88 mmol) in THF (25 mL) was added. The reaction mixture was stirred at 40° C. for 30 minutes, then cooled to room temperature. The solution was neutralized by Amberlite IR 120 (H+) ion exchange resin. The suspension was filtered, the filtrate was evaporated. The residue was purified by chromatography using EtOAc—hexane 1:4 as the mobile phase to give methyl 2-azido-6-O-tert-butyldiphenylsilyl-2-deoxy-3-O-(4-methoxybenzyl)-1-thio-β-D-glucopyranoside (10) (2.1 g, 91%)

Workup

temperaturecooled to room temperature
filtrationThe suspension was filtered
customthe filtrate was evaporated
customThe residue was purified by chromatography

Sources & evidence

ORD record: ord-78d0bc1932ee485398699db2d84c7e00
Source dataset: uspto-grants-2005_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06953850B1

Reaction notes

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