Methanol → HCID 67930761, compound

HRID 728217Notes

Reaction equation

HRID 728217 reaction equation
[N:1]([C@@H:4]1[CH2:9][C@H:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C@H:7]2[CH2:18][O:19][C@@H:5]1[O:6]2)=[N+]=[N-].[C:20]1(=O)[O:25][C:23](=[O:24])[C:22]2=[CH:26][CH:27]=[CH:28][CH:29]=[C:21]12.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CO>[C-]#N.C([N+](CCCC)(CCCC)CCCC)CCC.C1C=CC=CC=1>[CH2:11]([O:10][C@@H:8]1[C@H:7]2[CH2:18][O:19][C@H:5]([O:6]2)[C@H:4]([N:1]2[C:23](=[O:24])[C:22]3=[CH:26][CH:27]=[CH:28][CH:29]=[C:21]3[C:20]2=[O:25])[CH2:9]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 6811Phthalic AnhydrideHCID 11776TriphenylphosphineHCID 86745036HCID 86745036, compound

Product 1

HCID 67930761HCID 67930761, compoundYield 14.3%

Reagents, catalysts & solvents 2

HCID 165872Tetrabutylammonium CyanideCatalystHCID 241BenzeneSolvent

Procedure

1,6-Anhydro-2-azido-4-O-benzyl-2,3-dideoxy-β-D-ribo-hexoyranose (see Example 13) (1.0 g), phthalic anhydride (0.74 g), triphenylphosphine (1.21 g) and tetrabutylammonium cyanide (0.1 g) were heated under reflux in a nitrogen atmosphere in benzene (50 ml) for 40 h. Methanol (10 ml) was then added and the solution was allowed to stand at room temperature for 15 days. The solution was then evaporated and the residue was chromatographed on silica gel to yield the title compound as a crystaline solid (0.2 g, 14%) from amongst a variety of products (t.l.c.evidence). Recrystallised from ethanol it had m.p. 135°-136° C., [α]D -28.4°; 13C-nmr data: 100.4 (C-1), 51.1 (C-2), 25.0 (C-3), 76.5 and 75.7 (C-4 and C-5), 67.4 (C-6), 70.4 (PhCH2O), 167.7 (C=0), 156.0 and 131.8 (q-aromatic), 134.0, 128.3, 127.6, 127.5 and 123.3 (aromatic).

Workup

  1. customThe solution was then evaporated
  2. customthe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-c692fff9c9894297a2119817432a1baa
Source dataset
uspto-grants-1991_09
Patent number
US05047518

Reaction notes

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