alpha-D-Glucopyranose, 2,3,4,6-tetraacetate 1-(2,2,2-trichloroethanimidate) → HCID 12019997, compound

HRID 1982804Notes

Reaction equation

[C:1]([O:4][CH2:5][C:6]1[CH:7]=[CH:8][C:9]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([CH2:20][CH3:21])=[CH:16][CH:15]=2)=[C:10]([OH:12])[CH:11]=1)(=[O:3])[CH3:2].[C:22]([O:25][C@@H:26]1[C@@H:38]([O:39][C:40](=[O:42])[CH3:41])[C@H:37]([O:43][C:44](=[O:46])[CH3:45])[C@@H:36]([CH2:47][O:48][C:49](=[O:51])[CH3:50])[O:35][C@@H:27]1OC(=N)C(Cl)(Cl)Cl)(=[O:24])[CH3:23]>ClCCl>[C:22]([O:25][C@@H:26]1[C@@H:38]([O:39][C:40](=[O:42])[CH3:41])[C@H:37]([O:43][C:44](=[O:46])[CH3:45])[C@@H:36]([CH2:47][O:48][C:49](=[O:51])[CH3:50])[O:35][C@H:27]1[O:12][C:10]1[CH:11]=[C:6]([CH2:5][O:4][C:1](=[O:3])[CH3:2])[CH:7]=[CH:8][C:9]=1[CH2:13][C:14]1[CH:15]=[CH:16][C:17]([CH2:20][CH3:21])=[CH:18][CH:19]=1)(=[O:24])[CH3:23]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 5-acetoxymethyl-2-(4-ethylbenzyl)phenol (0.59 g) and 2,3,4,6-tetra-O-acetyl-1-O-trichloroacetoimidoyl-α-D-glucopyranose (1.1 g) in dichloromethane (15 mL) was added boron trifluoride diethyl ether complex (0.31 mL), and the mixture was stirred at 0° C. for 30 minutes. The reaction mixture was purified by column chromatography on silica gel (eluent: hexane/ethyl acetate=2/1-3/2) to give 5-acetoxymethyl-2-(4-ethylbenzyl)phenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside (1.0 g).

Workup

customThe reaction mixture was purified by column chromatography on silica gel (eluent: hexane/ethyl acetate=2/1-3/2)

Sources & evidence

ORD record: ord-72674656ca4049cd8f2b855b63f671ab
Source dataset: uspto-grants-2009_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07541341B2

Reaction notes

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