Water → HCID 86587179, compound

HRID 1761266Notes

Reaction equation

[C:1](Cl)(=[O:3])[CH3:2].[C:5]([O:8][C@H:9]1[C@H:22]([OH:23])[C@@H:21]([CH2:24][OH:25])[O:20][C@@H:11]([O:12][Si:13]([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14])[C@@H:10]1[N:26]=[N+:27]=[N-:28])(=[O:7])[CH3:6].O.CCOC(C)=O>N1C(C)=CC(C)=CC=1C>[C:5]([O:8][C@H:9]1[C@H:22]([OH:23])[C@@H:21]([CH2:24][O:25][C:1](=[O:3])[CH3:2])[O:20][C@@H:11]([O:12][Si:13]([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:14])[CH3:15])[C@@H:10]1[N:26]=[N+:27]=[N-:28])(=[O:7])[CH3:6]

Participants

Conditions

Temperature: -40 °C

Procedure

Acetyl chloride (1.5 mL, 21.1 mmol) was added slowly to a solution of tert-butyldimethylsilyl 3-O-acetyl-2-azido-2-deoxy-β-D-glucopyranoside (7.25 g, 20 mmol) in 2,4,6-collidine (47 mL) under nitrogen at −40° C. After stirring at −40° C. overnight, water was added. The mixture was poured into EtOAc and extracted with 1 N HCl, brine and saturated NaHCO3. The organic phase was dried over Na2SO4, filtered and the solvents were removed in vacuo. Flash chromatography on silica gel (Hexanes:EtOAc 5:1→4:1) afforded 7 (7.59 g, 18.8 mmol, 94%) as a colorless solid. [α]24D: −31.6 (c 1.00, CH2Cl2); IR (thin film on NaCl) 3459, 2112, 1747, 1233, 1042, 841 cm−1; 1H-NMR (300 MHz, CDCl3) δ 4.81-4.74 (m, 1H), 4.62 (d, J=7.6 Hz, 1H), 4.37-4.31 (m, 2H), 3.75-3.46 (m, 2H), 3.53 (dd, J=7.7, 10.3 Hz, 1H), 3.13-3.09 (m, 1H), 2.18 (s, 3H), 2.10 (s, 3H), 0.94 (s, 9H), 0.17 (s, 6H); 13C-NMR (75 MHz, CDCl3) δ 171.8, 171.5, 97.2, 75.5, 74.3, 69.8, 66.0, 63.4, 25.8, 21.2, 21.1, 18.2, −4.2, −5.0; FAB MS (C16H29N3O7Si) m/z (M+) calcd 403.1775, obsd 403.1779.

Workup

extractionextracted with 1 N HCl, brine and saturated NaHCO3
dry with materialThe organic phase was dried over Na2SO4
filtrationfiltered
customthe solvents were removed in vacuo

Sources & evidence

ORD record: ord-a58db1085f004a7c99109dfe742effe8
Source dataset: uspto-grants-2005_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06846917B2

Reaction notes

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