methyl alpha-D-glucopyranoside → HCID 88620164, compound

HRID 1608306Notes

Reaction equation

HRID 1608306 reaction equation
[CH3:1][O:2][C@H:3]1[O:8][C@H:7]([CH2:9][OH:10])[C@@H:6]([OH:11])[C@H:5]([OH:12])[C@H:4]1[OH:13].[C:14]([C:18]1[CH:19]=[C:20]([CH:24]=[C:25]([C:28]([CH3:31])([CH3:30])[CH3:29])[C:26]=1[OH:27])[C:21](Cl)=[O:22])([CH3:17])([CH3:16])[CH3:15]>N1C=CC=CC=1>[C:14]([C:18]1[CH:19]=[C:20]([CH:24]=[C:25]([C:28]([CH3:31])([CH3:30])[CH3:29])[C:26]=1[OH:27])[C:21]([O:13][C@@H:4]1[C@@H:5]([O:12][C:21](=[O:22])[C:20]2[CH:19]=[C:18]([C:14]([CH3:17])([CH3:16])[CH3:15])[C:26]([OH:27])=[C:25]([C:28]([CH3:31])([CH3:30])[CH3:29])[CH:24]=2)[C@H:6]([O:11][C:21](=[O:22])[C:20]2[CH:19]=[C:18]([C:14]([CH3:17])([CH3:16])[CH3:15])[C:26]([OH:27])=[C:25]([C:28]([CH3:31])([CH3:30])[CH3:29])[CH:24]=2)[C@@H:7]([CH2:9][O:10][C:21](=[O:22])[C:20]2[CH:24]=[C:25]([C:28]([CH3:29])([CH3:30])[CH3:31])[C:26]([OH:27])=[C:18]([C:14]([CH3:17])([CH3:16])[CH3:15])[CH:19]=2)[O:8][C@@H:3]1[O:2][CH3:1])=[O:22])([CH3:17])([CH3:16])[CH3:15]

Participants

4

Reactant 2

HCID 64947methyl alpha-D-glucopyranosideHCID 37871873,5-Di-tert-butyl-4-hydroxybenzoyl chloride

Product 1

HCID 88620164HCID 88620164, compoundYield 14%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 0.97 g (0.005 moles) methyl α-D-glucoside and 7.10 g (0.025 moles) 3,5-di-tert-butyl-4hydroxybenzoyl chloride in 50 ml dry pyridine was stirred and heated under a nitrogen atmosphere at 65°-70° C. for 21 hours. After a work-up in the same manner as that described in Example 1, 0.75 g (14% yield) of a light yellow solid, mp 163°-166° C., was isolated. This product was identified as the above-titled compound by IR and NMR analysis and by elemental analysis: Anal. Calc. for C67H94O14 : C, 71.63; H, 8.43.

Workup

  1. temperatureheated under a nitrogen atmosphere at 65°-70° C. for 21 hours

Sources & evidence

ORD record
ord-80c41981c0b24abd98967cd92e815cf7
Source dataset
uspto-grants-1989_09
Patent number
US04870157

Reaction notes

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