반응 #6156

ord-22f7dc4741844f499aa6a903ab0faa86

반응 방정식

CCCCCCCCCCC[C@@H]1C[C@H](O)[C@H](CCCCCC)C(=O)O1
(3S,4S,6R)-tetrahydro-3-hexyl-4-hydroxy-6-undecyl-2H-pyran-2-one
CC(C)(C)[Si](C)(C)Cl
t-butyldimethylchlorosilane
CCOCC
ether
CCCCCCCCCCC[C@@H]1C[C@H](O[Si](C)(C)C(C)(C)C)[C@H](CCCCCC)C(=O)O1
(3S,4S,6R)-tetrahydro-3-hexyl-4-[(t-butyldimethylsilyl)oxy]-6-undecyl-2H-pyran-2-one
수율 63.5%

용매

반응 조건

상세 조건
See reaction.notes.procedure_details.

후처리

  1. 1
    기타The reaction mixtures
  2. 2
    세척washed with 1N hydrochloric acid
  3. 3
    기타The organic phase was dried
  4. 4
    여과filtered
  5. 5
    기타evaporated
  6. 6
    기타The material obtained
  7. 7
    기타was chromatographed on silica gel

실험 절차

M)d) 1.5 g of (3S,4S,6R)-tetrahydro-3-hexyl-4-hydroxy-6-undecyl-2H-pyran-2-one were dissolved in 8 ml of DMF. 0.85 g of t-butyldimethylchlorosilane in 4 ml of DMF were then added dropwise. The mixture was stirred for 48 hours. The reaction mixtures was poured in to 100 ml of ether and washed with 1N hydrochloric acid. The organic phase was dried, filtered and evaporated. The material obtained was chromatographed on silica gel. There was obtained 1.26 g of (3S,4S,6R)-tetrahydro-3-hexyl-4-[(t-butyldimethylsilyl)oxy]-6-undecyl-2H-pyran-2-one, MS: 411 (M+ -t-butyl).

출처

DOI: 10.6084/m9.figshare.5104873.v1특허: US05246960uspto-grants-1993_09