tert-Butyldimethylsilyl chloride → Methyl 2-acetamido-2-deoxy-6-O-t-butyldimethylsilyl-beta-D-glucopyranoside

HRID 374601Notes

Reaction equation

HRID 374601 reaction equation
CO[C@H]1OC(CO)[C@H](O)[C@@H](O)[C@@H]1O.[C:14]([NH:17][C@@H:18]1[C@@H:25]([OH:26])[C@H:24]([OH:27])[C@@H:23]([CH2:28][OH:29])[O:22][C@H:19]1[O:20][CH3:21])(=[O:16])[CH3:15].[C:30]([Si:34]([CH3:37])([CH3:36])Cl)([CH3:33])([CH3:32])[CH3:31]>CN(C=O)C.N1C=CN=C1>[C:14]([NH:17][C@@H:18]1[C@@H:25]([OH:26])[C@H:24]([OH:27])[C@@H:23]([CH2:28][O:29][Si:34]([C:30]([CH3:33])([CH3:32])[CH3:31])([CH3:37])[CH3:36])[O:22][C@H:19]1[O:20][CH3:21])(=[O:16])[CH3:15]

Participants

6

Reactant 3

HCID 28928tert-Butyldimethylsilyl chlorideHCID 76607Methyl glucosideHCID 445750N-[(2R,3R,4R,5S,6R)-4,5-Dihydroxy-6-(hydroxymethyl)-2-methoxyoxan-3-yl]acetamide

Product 1

HCID 10760257Methyl 2-acetamido-2-deoxy-6-O-t-butyldimethylsilyl-beta-D-glucopyranoside

Reagents, catalysts & solvents 2

HCID 795ImidazoleSolventHCID 6228DimethylformamideSolvent

Procedure

This compound was prepared from the corresponding methyl glucoside, Methyl 2-acetamido-2-deoxy-β-D-glucopyranoside (Carbohydrates, Ed. Collins, P. M., Chapman and Hall, New York, 1987, p. 414) by treatment with t-butyldimethylchlorosilane in DMF and imidazole. 1H NMR δ0.00 (2Xs, 6H), 0.80 (2Xs, 9H), 1.98 (s, br, 3H), 3.20-3.32 (m, 1H), 3.32-3.50 (s superimposed on m 5H), 3.59 (dd, J=12, 8, 1H), 3.76, 3.84 (ABX, JAB=18, 2H), 4.28 (d, J=8, 1H), 6.42 (d br J=4, 3H).

Sources & evidence

ORD record
ord-4cc3ec1f2b6c4245857436aabebbea17
Source dataset
uspto-grants-1996_01
Patent number
US05481006

Reaction notes

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