Tributylstannane → HCID 14057275, compound

HRID 863408Notes

Reaction equation

HRID 863408 reaction equation
C1(O[C@@H:8]2[C@@H:15]([OH:16])[C@H:14]([CH:17]=S)[O:13][C@@:10](C=O)([O:11][CH3:12])[C@@H:9]2[OH:21])C=CC=CC=1.CC(N=NC(C#N)(C)C)(C#N)C.[SnH](CCCC)(CCCC)CCCC>C1(C)C=CC=CC=1>[O:11]([CH3:12])[C@@H:10]1[O:13][C@@H:14]([CH3:17])[C@H:15]([OH:16])[CH2:8][C@H:9]1[OH:21]

Participants

5

Reactant 3

HCID 5948TributylstannaneHCID 6547AzobisisobutyronitrileHCID 86752139HCID 86752139, compound

Product 1

HCID 14057275HCID 14057275, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of methyl 6-deoxy-3-O-phenylthiono-formyl-α-L-mannopyranoside, 2,4-O-dibenzoate (3.5 g, 6.7 mmol) in toluene (120 mL) is added AIBN (55 mg, 0.34 mmol) and n-Bu3SnH (2.6 mL, 13.4 mmol). The solution is deoxygenated by passing through N2 gas for 20 min. The reaction flask is placed in an oil bath (120° C.). After 1.5 h TLC indicates that the reaction is complete. Evaporation of the solvent yields a residue. Purification by chromatography (eluting with hexane/ethyl acetate in gradient from 500:20 to 500:50) yields methyl 3,6-dideoxy-α-L-mannopyranoside, 2,4-O-dibenzoate (1.8 g, 70% in two steps from 6-deoxy-α-L-mannopyranoside, 2,4-O-dibenzoate).

Workup

  1. customThe solution is deoxygenated
  2. customThe reaction flask is placed in an oil bath
  3. custom(120° C.)
  4. waitAfter 1.5 h TLC indicates that the reaction
  5. customEvaporation of the solvent
  6. customyields a residue
  7. customPurification
  8. washby chromatography (eluting with hexane/ethyl acetate in gradient from 500:20 to 500:50)

Sources & evidence

ORD record
ord-c43ea81a0fd54f969682bba3cfb95127
Source dataset
uspto-grants-1998_02
Patent number
US05721217

Reaction notes

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