Tetrahydrofuran → HCID 54244290, compound

HRID 985986Notes

Reaction equation

HRID 985986 reaction equation
C(OC([NH:11][C@H:12]([C@H:15]([C@@H:17]([C@@H:19]([CH2:21][OH:22])[OH:20])[OH:18])[OH:16])[CH:13]=O)=O)C1C=CC=CC=1.[CH2:23]([NH2:37])[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36].[O:38]1[CH2:42][CH2:41][CH2:40][CH2:39]1>CN(C)C=O>[CH2:23]([N:37]([CH:13]1[O:20][C@H:19]([CH2:21][OH:22])[C@@H:17]([OH:18])[C@H:15]([OH:16])[C@H:12]1[NH2:11])[C:39](=[O:38])[CH2:40][CH2:41][CH2:42][CH2:36][CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH3:23])[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 16217TetradecylamineHCID 228512932-{[(Benzyloxy)carbonyl]amino}-2-deoxy-D-glucose

Product 1

HCID 54244290HCID 54244290, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

3.1 g of 2-(benzyloxycarbonylamino)-2-deoxy-D-glucose were dissolved in 40 ml of dimethylformamide, 3.2 g of tetradecylamine were added and the mixture was warmed at 80° C. for 4 hours, under a water pump vacuum. The mixture was cooled to room temperature, diluted with 50 ml of tetrahydrofuran and stirred in the presence of 5 ml of ion exchanger SC 108 (H+ form). The exchanger resin was filtered off and 1 g of sodium carbonate and 3.3 g of stearoyl chloride were added to the filtrate. After the mixture had been stirred for five hours, the solid constituents were filtered off and the filtrate was evaporated in vacuo. The resulting syrup was purified by column chromatography on silica gel (eluting agent methylene chloride/methanol=20:1).

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. filtrationThe exchanger resin was filtered off
  3. addition1 g of sodium carbonate and 3.3 g of stearoyl chloride were added to the filtrate
  4. filtrationthe solid constituents were filtered off
  5. customthe filtrate was evaporated in vacuo
  6. customThe resulting syrup was purified by column chromatography on silica gel (eluting agent methylene chloride/methanol=20:1)

Sources & evidence

ORD record
ord-bcc17d8ce8cc4242bd3995bd095814ab
Source dataset
uspto-grants-1987_12
Patent number
US04710491

Reaction notes

Loading…