Benzyl Chloride → methyl 2,3,4,6-tetra-O-benzyl-alpha-D-glucopyranoside

HRID 1599978Notes

Reaction equation

HRID 1599978 reaction equation
[CH3:1][C@@]1(O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)O.[CH2:14]([O:21][C@@H:22]1[C@@H:28]([O:29][CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C@H:27]([O:37][CH2:38][C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[C@@H:26]([CH2:45][O:46][CH2:47][C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)[O:25][C@@H:23]1[OH:24])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(Cl)C1C=CC=CC=1.[OH-].[K+]>O>[CH2:14]([O:21][C@@H:22]1[C@@H:28]([O:29][CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C@H:27]([O:37][CH2:38][C:39]2[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=2)[C@@H:26]([CH2:45][O:46][CH2:47][C:48]2[CH:49]=[CH:50][CH:51]=[CH:52][CH:53]=2)[O:25][C@@H:23]1[O:24][CH3:1])[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 7503Benzyl ChlorideHCID 14797Potassium HydroxideHCID 131720627HCID 131720627, compound

Product 1

HCID 10840491methyl 2,3,4,6-tetra-O-benzyl-alpha-D-glucopyranoside

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Preparation of 2,3,4,6-Tetra-O-benzyl-α-D-glucopyranose Methyl-α-D-glucopyranose (100 g, 0.516 mol) is suspended in benzyl chloride (400 mL, 3.5 mol) with KOH pellets (336 g, 6 mol), and the mixture is stirred using a mechanical stirrer at 120°-130° C. for 3 h. The reaction mixture is cooled and water (800 mL) is added to dissolve the crystalline mass, which is extracted with ether (2×200 mL). The combined organic layer is washed with water (2×500 mL) and dried (Na2SO4). The solvents are removed by vacuum distillationto give the crude methyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside for the next reaction.

Workup

  1. customat 120°-130° C.
  2. customfor 3 h
  3. temperatureThe reaction mixture is cooled
  4. dissolutionto dissolve the crystalline mass, which
  5. extractionis extracted with ether (2×200 mL)
  6. washThe combined organic layer is washed with water (2×500 mL)
  7. dry with materialdried (Na2SO4)
  8. customThe solvents are removed by vacuum

Sources & evidence

ORD record
ord-269f3f6e58054970bf1f033102b48936
Source dataset
uspto-grants-1998_04
Patent number
US05744453

Reaction notes

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