Sodium → HCID 54344857, compound

HRID 839573Notes

Reaction equation

HRID 839573 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 1 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-722833147e3442d28446678d605e9869
Source dataset
uspto-grants-1978_06
Patent number
US04096249

Reaction notes

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