1,3-Dithiane, 1,1,3,3-tetraoxide → HCID 22852345, compound

Participants

Reaction Steps

In analogy to Example 3, there are obtained from2-[(2S,3S)-3-amino-4-cyclohexyl-2-hydroxy-butyl]-1,3-dithiane 1, 1,3,3-tetroxide or from 2-[(3S, 4S)-4-amino-5-cyclohexyl-3-hydroxypentyl]-1,3-dithiane 1,1,3,3-tetroxide or from 2-[(4S,5S)-5-amino-6-cyclohexyl-4-hydroxy-hexyl ]-1,3-dithiane 1,1,3,3-tetroxide [dihydrochloride, m.p. 209°-210° , FAB 382, obtainable from (4S,5S)-3-BOC-4-cyclohexyl-methyl-5-(2-methansulfonyloxy-ethyl)-2,2-di-methyl-oxazolidine via the corresponding 5-(2-cyanoethyl)-, 5-(2-carboxyethyl)-(m.p. 190° (decomposition)), 5-(2-methoxy-carbonyl-ethyl)-(oil; FAB 384), 5-(3-hydroxy-propyl)-(m.p. 60°-61°; FAB 356) and 5-(3-methanesulfonyloxy-propyl)-compounds (m.p. 63°-64°, FAB 434), react ion of the last mentioned compound with 1,3-dithiane 1,1,3,3-tetroxide to yield 2-[3-((4S,5S)-3-BOC-4-cyclohexylmethyl-2,2-dimethyl- 5-oxazolidinyl)-propyl]-1,3-dithiane 1,1,3,3-tetroxide (FAB 522) and cleavage with methanolic hydrochloric acid at 25° the following 1,3-dithiane 1,1,3,3-tetroxides:

Provenance & Evidence