Sodium Hydroxide → HCID 69820884, compound

HRID 1265309Notes

Reaction equation

HRID 1265309 reaction equation
[CH2:1]([O:8][C@@H:9]1[C@@H:15]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C@H:14]([O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C@@H:13]([CH2:32][O:33][CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[O:12][CH:10]1[OH:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].C[Si](C)(C(C)(C)C)[O:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51]Br>[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.ClCCl>[CH2:1]([O:8][C@@H:9]1[C@@H:15]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C@H:14]([O:24][CH2:25][C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[C@@H:13]([CH2:32][O:33][CH2:34][C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=2)[O:12][CH:10]1[O:11][CH2:51][CH2:50][CH2:49][CH2:48][CH2:47][CH2:46][OH:45])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 4260352(6-Bromohexyloxy)-tert-butyldimethylsilaneHCID 109405022,3,4,6-Tetrakis-O-(phenylmethyl)-D-glucopyranose

Product 1

HCID 69820884HCID 69820884, compound

Reagents, catalysts & solvents 2

HCID 70681Tetrabutylammonium ChlorideCatalystHCID 6344DichloromethaneSolvent3×

Conditions

Temperature
10 °C

Procedure

A mixture that consists of 54.1 g (100 mmol) of 2,3,4,6-tetra-O-benzylglucopyranose, 1.39 g (5 mmol) of tetrabutylammonium chloride and 24 g (600 mmol) of fine-powder sodium hydroxide in 350 ml of dichloromethane is cooled to 10° C. At 10° C., 41.3 g (140 mmol) of 1-(dimethyl-tert-butylsilyloxy)-6-bromohexane, dissolved in 100 ml of dichloromethane, is added in drops over 50 minutes while being stirred vigorously. It is stirred for three hours at 10° C. 350 ml of dichloromethane is added, solid is filtered out, and the filtrate is evaporated to the dry state in a vacuum. The residue is taken up in 350 ml of acetonitrile, and 52.3 g (200 ml) of tetrabutylammonium fluoride is added (as a monohydrate). It is stirred for three hours at 50° C. The solution is evaporated to the dry state, and the residue is chromatographed on silica gel (mobile solvent: dichloromethane/ethanol=20:1).

Workup

  1. additionis added in drops over 50 minutes
  2. stirringIt is stirred for three hours at 10° C
  3. filtrationsolid is filtered out
  4. customthe filtrate is evaporated to the dry state in a vacuum
  5. addition52.3 g (200 ml) of tetrabutylammonium fluoride is added (as a monohydrate)
  6. stirringIt is stirred for three hours at 50° C
  7. customThe solution is evaporated to the dry state
  8. customthe residue is chromatographed on silica gel (mobile solvent: dichloromethane/ethanol=20:1)

Sources & evidence

ORD record
ord-16be81648f10428bb23840a32c21f43d
Source dataset
uspto-grants-2003_04
Patent number
US06545135B2

Reaction notes

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