Pyridine → HCID 131721483, compound

HRID 1858879Notes

Reaction equation

HRID 1858879 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, compoundYield 93%

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, 93% 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-f492a3af2c484225b554db1b7e0ab62d
Source dataset
uspto-grants-2000_11
Patent number
US06153396

Reaction notes

Loading…