Sodium borohydride → HCID 15734882, compound

HRID 1199275Notes

Reaction equation

HRID 1199275 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][C:10]1([CH:41]([Br:43])[Br:42])[OH:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+].C(O[C@H]([C@H]([C@@H]([C@@H](COCC1C=CC=CC=1)O)OCC1C=CC=CC=1)OCC1C=CC=CC=1)C(C(SC)SC)O)C1C=CC=CC=1>O1CCCC1>[CH2:1]([O:8][C@H:9]([C@H:15]([C@@H:14]([C@@H:13]([CH2:32][O:33][CH2:34][C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1)[OH:12])[O:24][CH2:25][C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)[O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH:10]([CH:41]([Br:43])[Br:42])[OH:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 4311764Sodium borohydrideHCID 15734879HCID 15734879, compoundHCID 18637752HCID 18637752, compound

Product 1

HCID 15734882HCID 15734882, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2,3,4,6-tetra-O-benzyl-1-C-(dibromomethyl)-D-glucopyranose (3.15 g) in tetrahydrofuran (32 mL) was added sodium borohydride (1.6 g) under cooling with ice-water and the mixture was stirred at the same temperature for 1 hour and then at room temperature overnight. The mixture was evaporated under reduced pressure, and the residue was partitioned between ethyl acetate (150 mL) and water (50 mL). The organic layer was washed with 2N hydrochloric acid and saturated sodium hydrogencarbonate solution, dried over anhydrous sodium sulfate, and evaporated under reduced pressure. The residue was chromatographed on a column of silica gel (400 mL) with toluene-ethyl acetate (6:1). The eluate was evaporated to dryness under reduced pressure to give a mixture of (1R)- and (1S)- isomers of 2,3,4,6-tetra-O-benzyl-1-C-(dibromomethyl)-D-glucitol (2.13 g) as a colorless syrup. NMR (CDCl3 +D2O) δ: 3.5-4.9 (15H, m), 5.68 (d, J=8 Hz) and 6.13 (d, J=3 Hz) (total 1H), 7.1-7.5 (20H, m). Elemental analysis for C35H38Br2O6 : Calc.(%): C, 58.84; H, 5.36; Br, 22.37,. Found(%): C, 59.15; H, 5.23; Br, 21.94.

Workup

  1. customat room temperature
  2. customovernight
  3. customThe mixture was evaporated under reduced pressure
  4. customthe residue was partitioned between ethyl acetate (150 mL) and water (50 mL)
  5. washThe organic layer was washed with 2N hydrochloric acid and saturated sodium hydrogencarbonate solution
  6. dry with materialdried over anhydrous sodium sulfate
  7. customevaporated under reduced pressure
  8. customThe residue was chromatographed on a column of silica gel (400 mL) with toluene-ethyl acetate (6:1)
  9. customThe eluate was evaporated to dryness under reduced pressure
  10. customto give

Sources & evidence

ORD record
ord-5eeb96babe514a3e904b6ee24994ebe4
Source dataset
uspto-grants-1990_02
Patent number
US04898986

Reaction notes

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