Sodium → HCID 54344857, compound

HRID 839578Notes

Reaction equation

HRID 839578 reaction equation
[C:1]([S:20][C@@H:21]1[O:38][C@H:37]([CH2:39][O:40]C(=O)C)[C@@H:32]([O:33]C(=O)C)[C@H:27]([O:28]C(=O)C)[C@H:22]1[O:23]C(=O)C)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[O-].[Na+].[Na]>CO>[C:1]([S:20][C@@H:21]1[O:38][C@H:37]([CH2:39][OH:40])[C@@H:32]([OH:33])[C@H:27]([OH:28])[C@H:22]1[OH:23])([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 5360545SodiumHCID 10942334Sodium MethoxideHCID 13633137HCID 13633137, compound

Product 1

HCID 54344857HCID 54344857, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

S-Trityl-2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranose (21.0 g.) was suspended in 90 ml. of methanol, cooled to -15° C. and a solution of sodium methoxide prepared from 0.21 g. of sodium and 75 ml. of methanol was added. The mixture was stirred for one hour at room temperature, then concentrated under reduced pressure to give a solid residue. The residue was triturated with water, then chloroform was added. The mixture was filtered and concentrated to give a solid residue which was dried by azeotropic distillation in benzene. Further evaporation of solvent and drying in vacuo gave S-trityl-1-thio-β-D-glucopyranose.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customto give a solid residue
  3. customThe residue was triturated with water
  4. additionchloroform was added
  5. filtrationThe mixture was filtered
  6. concentrationconcentrated
  7. customto give a solid residue which
  8. dry with materialwas dried by azeotropic distillation in benzene
  9. customFurther evaporation of solvent
  10. customdrying in vacuo

Sources & evidence

ORD record
ord-a8b20efd0c6e4f7982fe8a28a159f838
Source dataset
uspto-grants-1978_06
Patent number
US04096250

Reaction notes

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