Tetrahydrofuran → HCID 22808778, compound

HRID 426724Notes

Reaction equation

HRID 426724 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[O:7]1CC[CH2:9][CH2:8]1.[N:12]([CH2:15][C@H:16]1[O:21][CH:20]=[CH:19][C@@H:18]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C@@H:17]1[O:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)=[N+]=[N-]>CCOCC>[C:8]([NH:12][CH2:15][C@H:16]1[O:21][CH:20]=[CH:19][C@@H:18]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C@@H:17]1[O:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)(=[O:7])[CH3:9]

Participants

5

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 21226445Aluminium lithium hydrideHCID 22808781HCID 22808781, compound

Product 1

HCID 22808778HCID 22808778, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Stir a suspension of 760 mg. of lithium aluminum hydride in 50 ml. of tetrahydrofuran and to this add dropwise a solution of 2.98 gm. of 6-azido-6-deoxy-3,4di-O-benzyl-D-glucal in 30 ml. of tetrahyrofuran. Heat the mixture under reflux for 4 hours, cool and add wet ether, filter evaporate the filtrate to a residue. To the residue add 3 ml. of acetic anhydride and 10 ml. of distilled pyridine, stir for 2 hours and remove the solvent, crystallize the residue in chloroform: hexane to obtain 6-acetamido-6-deoxy-3,4-di-O-benzyl-D-glucal [α]26D - 41.8° (EtOH); pmr (CDCl3) δ 1.86 (3H, s, COCH3), 3.65 (2H, m, -CH2 -N), 4.6 (2H, m, ArCH2), 4.75 (2H, m, Ar-CH2), 4.9 (1H, dd, J=3, 6Hz, H-2), 6.45 (1H, dd, J=1.5, 6Hz, H-1); ν max (nujol) 3250, 1640 cm-1.

Workup

  1. additiona suspension of 760 mg
  2. temperatureHeat the mixture
  3. temperatureunder reflux for 4 hours
  4. temperaturecool
  5. filtrationfilter
  6. customevaporate the filtrate to a residue
  7. additionTo the residue add 3 ml
  8. stirringof distilled pyridine, stir for 2 hours
  9. customremove the solvent
  10. customcrystallize the residue in chloroform

Sources & evidence

ORD record
ord-7a6a5f435b4545f1b5fc53e65efcff2e
Source dataset
uspto-grants-1979_10
Patent number
US04171356

Reaction notes

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