Sodium Azide → HCID 10872412, compound

HRID 429739Notes

Reaction equation

HRID 429739 reaction equation
C([C@:4]1([OH:19])[C@H:9]([OH:10])[C@@H:8]([CH2:11][OH:12])[O:7][C:6](C(=O)C)=[C:5]1C(=O)C)(=O)C.[N-:20]=[N+:21]=[N-:22].[Na+].[CH3:24][C:25]([O-:27])=[O:26].[Na+]>CC#N.CC(O)=O>[N:20]([C@@H:5]1[C@@H:4]([OH:19])[C@H:9]([OH:10])[C@@H:8]([CH2:11][OH:12])[O:7][CH:6]1[O:26][CH2:25][CH3:24])=[N+:21]=[N-:22].[N:20]([C@@H:5]1[C@@H:4]([O:19][C:6](=[O:7])[CH3:5])[C@H:9]([O:10][C:9](=[O:10])[CH3:4])[C@@H:8]([CH2:11][O:12][C:11](=[O:12])[CH3:8])[O:7][CH:6]1[O:26][C:25](=[O:27])[CH3:24])=[N+:21]=[N-:22]

Participants

7

Reactant 3

HCID 33557Sodium AzideHCID 517045Sodium AcetateHCID 22843480HCID 22843480, compound

Product 2

HCID 10872412HCID 10872412, compoundHCID 54566069HCID 54566069, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6342AcetonitrileSolvent

Procedure

The acceptor, ethyl 2-azido-2-deoxy-D-glucopyranoside was prepared as follows: Triacetyl-D-glucal was azidonitrated [Lemieux et al., Can. J. Chem., 57:1244 (1979)] [NaN3 and Ce(NH4)2(NO3)6 in CH3CN] and acetolyzed (NaOAc in AcOH) to give 2-azido-1,3,4,6-tetra-O-acetyl-2-deoxy-D-glucopyranose, which was treated with TiBr4 in CH2Cl2 and EtOAc, giving a glycosyl bromide, then glycosylated with EtOH in the presence of AgOTf and MS 4 Å in CH2Cl2 to give after O-deacetylation with NaOMe in MeOH, ethyl 2-azido-2-deoxy-D-glucopyranoside (22 percent overall yield) as a mixture of α and β 1:1.5. 1H NMR (D2O) δ: 1.21 (t, J 7.80 Hz, OCH2CH3 of β anomer), 1.22 (t, J 7.80 Hz, OCH2CH3), 2.99 (dd, J 7.43, 9.83 Hz, H-2 of β anomer), 5.11 (d, J 3.58 Hz, H-1 of a anomer). HRMS calcd for C8H15N3O5Cs (M+Cs+) 366.0066, found 366.0066.

Sources & evidence

ORD record
ord-14dce17415ab4811b3162cf994db17b8
Source dataset
uspto-grants-2001_11
Patent number
US06319695B1

Reaction notes

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