Sulfuric Acid → 2,3,4,6-Tetrakis-O-(phenylmethyl)-alpha-D-glucopyranose

HRID 1779845Notes

Reaction equation

HRID 1779845 reaction equation
[CH2:1]([O:8][C@@H:9]1[C@@H:16]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C@H:15]([O:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C@@H:14]([CH2:33][O:34][CH2:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[O:13][C@@H:10]1[O:11]C)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(=O)(=O)(O)O>C(O)(=O)C>[CH2:1]([O:8][C@@H:9]1[C@@H:16]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C@H:15]([O:25][CH2:26][C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[C@@H:14]([CH2:33][O:34][CH2:35][C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=2)[O:13][C@@H:10]1[OH:11])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 10840491methyl 2,3,4,6-tetra-O-benzyl-alpha-D-glucopyranoside

Product 1

HCID 117312562,3,4,6-Tetrakis-O-(phenylmethyl)-alpha-D-glucopyranoseYield 53.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

The crude methyl 2,3,4,6-tetra-O-benzyl-D-glucopyranoside 10 (210 g) is dissolved in glacial acetic acid (500 mL) and the solution is heated to nearly boiling. Hot sulfuric acid solution (3N, 130 mL) is added slowly. Heat is periodically increased and more acetic acid (20 mL) is added to dissolve any precipitate. The final cloudy solution is heated at 100°-110° C. for 2 h. After cooling, crude crystalline product is isolated by filtration and washed several times with methanol to yield product 11 as white crystals (109 g, 53%): mp. 168°-170° C. (Lit. 169°-171° C.).

Workup

  1. temperaturethe solution is heated
  2. temperatureHeat
  3. temperatureis periodically increased
  4. dissolutionto dissolve any precipitate
  5. temperatureThe final cloudy solution is heated at 100°-110° C. for 2 h
  6. temperatureAfter cooling
  7. customcrude crystalline product is isolated by filtration
  8. washwashed several times with methanol

Sources & evidence

ORD record
ord-fddca642b408429cb4ea9819ab09bd2b
Source dataset
uspto-grants-1997_05
Patent number
US05627270

Reaction notes

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