Benzyl chloroformate → Methyl N-benzyloxycarbonyl-3,5-di-O-benzyl-2,6-dideoxy-2,6-imino-L-gulofuranoside

HRID 6432Notes

Reaction equation

HRID 6432 reaction equation
[CH2:1]([O:8][C@H:9]1[C@H:15]2[C@H:16]([CH2:25][NH:26][C@@H:10]1[CH:11]([O:14]2)[O:12][CH3:13])[O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)(O)[O-].[Na+].[CH2:32]([O:39][C:40](Cl)=[O:41])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>C(OCC)C>[CH2:32]([O:39][C:40]([N:26]1[CH2:25][C@H:16]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C@@H:15]2[C@H:9]([O:8][CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[C@H:10]1[CH:11]([O:14]2)[O:12][CH3:13])=[O:41])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

5

Reactant 3

HCID 10387Benzyl chloroformateHCID 516892Sodium BicarbonateHCID 54038294Methyl 3,5-di-O-benzyl-2,6-dideoxy-2,6-imino-L-gulofuranoside

Product 1

HCID 11145393Methyl N-benzyloxycarbonyl-3,5-di-O-benzyl-2,6-dideoxy-2,6-imino-L-gulofuranoside

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To the crude amine (15), in a solution of diethyl ether:saturated sodium bicarbonate (3:2, 20 ml), was added benzylchloroformate (0.2 ml, 1.2 mmol). The reaction was then stirred, at such a rate as to make it one phase, for 2 hours. The aqueous phase was then separated and washed with diethyl ether (3×10 ml). The combined ethereal layers were then dried (sodium sulphate) and the solvent removed in vacuo. Purification by flash chromatography (0-50%, diethyl ether/hexane) then yielded methyl N-benzyloxycarbonyl-3,5-di-O-benzyl-2,6-deoxy-2,6-imino-L-gulofuranoside (16), as a colorless oil (200 mg, 67% from azidotriflate). νmax (CHCl3): 1685, 750, 700 cm-1.

Workup

  1. customThe aqueous phase was then separated
  2. washwashed with diethyl ether (3×10 ml)
  3. dry with materialThe combined ethereal layers were then dried (sodium sulphate)
  4. customthe solvent removed in vacuo
  5. customPurification by flash chromatography (0-50%, diethyl ether/hexane)

Sources & evidence

ORD record
ord-7c1e2ef533ec401fb17ad35bd72360ba
Source dataset
uspto-grants-1993_09
Patent number
US05248779

Reaction notes

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