(Diethylamino)sulfur trifluoride → HCID 10855816, compound

HRID 481288Notes

Reaction equation

HRID 481288 reaction equation
[O:1]([CH3:11])[C@H:2]1[O:10][CH2:9][C@@H:7]([OH:8])[C@H:5]([OH:6])[C@@H:3]1[OH:4].C(N(S(F)(F)[F:18])CC)C>>[F:18][C@H:7]1[CH2:9][O:10][C@@H:2]([O:1][CH3:11])[C@@H:3]([OH:4])[C@H:5]1[OH:6].[O:1]([CH3:11])[C@H:2]1[O:10][CH2:9][C@@H:7]([OH:8])[C@H:5]([OH:6])[C@@H:3]1[OH:4]

Participants

4

Reactant 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 10855816HCID 10855816, compound3×

Product 2

HCID 10855816HCID 10855816, compoundHCID 54066665HCID 54066665, compound

Procedure

A known compound, methyl α-D-lyxopyranoside [Compound 50] of the formula ##STR90## is reacted with diethylaminosulfur trifluoride [(C2H5)2 NSF3 ] to fluorinate selectively only the 4-hydroxyl group of Compound 50, whereby there is produced methyl 4-deoxy-4-fluoro-α-L-ribopyranoside [Compound 51] of the formula ##STR91## as a 4-deoxy-4-fluoro derivative of Compound 50, with accompanying reversion of the steric configuration of the starting compound.

Sources & evidence

ORD record
ord-f366754bc61f4f7b85db767dce135c6c
Source dataset
uspto-grants-1998_08
Patent number
US05789386

Reaction notes

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