Pyridine → HCID 131721483, compound

HRID 611491Notes

Reaction equation

HRID 611491 reaction equation
[C:1]([C@@:9]1([OH:37])[C@@H:17]([O:18][C:19](=[O:26])[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C@H:16]([O:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C@@H:15]([CH2:35][OH:36])[O:14][C@H:10]1[S:11][CH2:12][CH3:13])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CC=CC=1.[C:44](OC(=O)C)(=[O:46])[CH3:45]>ClCCl>[C:44]([O:36][CH2:35][C@H:15]1[O:14][C@@H:10]([S:11][CH2:12][CH3:13])[C@:9]([C:1](=[O:8])[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)([OH:37])[C@@H:17]([O:18][C:19](=[O:26])[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C@@H:16]1[O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)(=[O:46])[CH3:45]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 131721484HCID 131721484, compound

Product 1

HCID 131721483HCID 131721483, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Ethyl 2,3-O-dibenzoyl-4-O-benzyl-1-thio-β-D-glucohexopyranoside (200 mg, 0.38 mmol) was dissolved in an ice-cooled mixture of pyridine and acetic anhydride (1:1, 6 Å). The mixture was stirred and attained at room temperature overnight. The mixture was diluted with dichloromethane, washed with satd. aq. sodium hydrogen carbonate and water and dried over sodium sulphate. The solvents were removed under reduced pressure and the residue was subjected to flash chromatography on silica gel (toluene-acetonitrile 6:1) to yield 204 mg, 930 of ethyl 6-O-acetyl-2,3-O-dibenzoyl-4-O-benzyl-1-thio-β-D-glucohexopyranoside.

Workup

  1. temperaturecooled
  2. washwashed with satd
  3. dry with materialaq. sodium hydrogen carbonate and water and dried over sodium sulphate
  4. customThe solvents were removed under reduced pressure

Sources & evidence

ORD record
ord-15a2f708402a44289c6ffed791c9693b
Source dataset
uspto-grants-1999_12
Patent number
US06001823

Reaction notes

Loading…