Imidazole → Methyl 2-deoxy-6-O-t--butyldimethyl-alphaD-glucopyranoside

HRID 374602Notes

Reaction equation

HRID 374602 reaction equation
[CH3:1][O:2][C@H:3]1[O:8][CH:7]([CH2:9][OH:10])[C@H:6]([OH:11])[C@@H:5]([OH:12])[C@@H:4]1O.O(C)[C@H]1O[C@H](CO)[C@@H](O)[C@H](O)C1.C(N[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC)(=O)C.[C:42]([Si](C)(C)Cl)([CH3:45])([CH3:44])[CH3:43].N1[CH:54]=[CH:53]N=C1>CN(C=O)C>[C:42]([O:10][CH2:9][C@H:7]1[O:8][C@:3]([CH3:4])([O:2][CH3:1])[C@H:53]([CH3:54])[C@@H:5]([OH:12])[C@@H:6]1[OH:11])([CH3:45])([CH3:44])[CH3:43]

Participants

7

Reactant 5

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 76607Methyl glucosideHCID 445750N-[(2R,3R,4R,5S,6R)-4,5-Dihydroxy-6-(hydroxymethyl)-2-methoxyoxan-3-yl]acetamideHCID 9920525Methyl 2-deoxy-alpha-D-glucopyranoside

Product 1

HCID 53829532Methyl 2-deoxy-6-O-t--butyldimethyl-alphaD-glucopyranoside

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

This compound was prepared from the corresponding methyl glucoside, Methyl 2-deoxy-α-D-glucopyranoside. (Carbohydrates, Ed. Collins, P. M., Chapman and Hall, New York, 1987, p. 352) by treatment with t-butyldimethylchlorosilane in DMF and imidazole. 1H NMR δ4.73 (d, 1, J=3 Hz), 3.85-3.78 (m, 4), 3.55-3.46 (m, 2), 3.35 (m, 1), 3.29 (s, 3), 2.05 (m, 1), 1.61 (m, 1), 0.88 (m, 9), 0.07 (m, 6).

Sources & evidence

ORD record
ord-a833661a22f64c94a4a79af06f1d4eba
Source dataset
uspto-grants-1996_01
Patent number
US05481006

Reaction notes

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