Dimethylformamide → HCID 178454992, compound

HRID 1656003Notes

Reaction equation

N1[C@H:9]([CH2:10][OH:11])[C@@H:7]([OH:8])[C@H:5]([OH:6])[C@@H:3]([OH:4])C1.[Si:12](/[CH:19]=[CH:20]/[CH2:21]O)([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13].CS([O-])(=O)=[O:25].C(N(CC)CC)C.C[N:36](C)[CH:37]=[O:38]>>[Si:12](/[CH:19]=[CH:20]/[CH2:21][N:36]=[C:37]([OH:38])[C@@H:10]([C@H:9]([C@@H:7]([C@@H:5]([CH2:3][OH:4])[OH:6])[OH:8])[OH:25])[OH:11])([C:15]([CH3:16])([CH3:17])[CH3:18])([CH3:13])[CH3:14]

Participants

Reactant 5

HCID 6228Dimethylformamide

HCID 8471Triethylamine

HCID 29435Deoxynojirimycin

HCID 85257Methanesulfonate

HCID 11829925HCID 11829925, compound

Product 1

HCID 178454992HCID 178454992, compound

Conditions

Temperature: 80 °C

Procedure

Following the same procedure as in Example 40, 0.3 g (1.85 mmol) of 1, 5-dideoxy-1,5-imino-D-glucitol, 0.65 g (2.6 mmol) of (E)-3-(t-butyldimethylsilyl)-2-propen-1-ol, methanesulfonate and 0.48 ml (3.4 mmol) of triethylamine in 13 ml of dimethylformamide are heated at 80° C. overnight. Solvents are removed under reduced pressure and the residue is flash chromatographed on a silica gel column eluted with dichloromethane-methanol 100:0 to 90:10 to give after methanol-water recristallization 0.15 g (35%) of expected {[(E)-3-(t-butyldimethylsilyl)-2-propenyl]imino}-D-glucitol as white crystals.

Workup

customSolvents are removed under reduced pressure
customchromatographed on a silica gel column
washeluted with dichloromethane-methanol 100:0 to 90:10

Sources & evidence

ORD record: ord-e3a1333c18664124b111fb1ed0d5933a
Source dataset: uspto-grants-1993_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05252587

Reaction notes

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