89117-66-8

Upstream product

• 3173-56-6 benzyl isothiocyanate 
• 89117-56-6 (2R,3R)-2,3-epoxyocatadec-4-yn-1-ol 
• 100-46-9 benzylamine 
• 89117-58-8 Carbonic acid 4-nitro-phenyl ester (S)-3-pentadec-1-ynyl-oxiranylmethyl ester 
• 89117-56-6 ((2R,3S)-3-Pentadec-1-ynyl-oxiranyl)-methanol 
• 765-13-9 pentadec-1-yne 
• 105243-56-9 (E)-3,4,5,6-tetrahydro-2-(octadec-2-en-4-yn-1-yloxy)-2H-pyrane 
• 89117-55-5 (E)-octadec-2-en-4-yn-1-ol 
• 5073-11-0 (E)-5-(tetrahydropyran-2-yloxy)pent-3-en-1-yne 
• 765-09-3 1-bromotridecane 
• 89117-59-9 Benzyl-carbamic acid (S)-3-pentadec-1-ynyl-oxiranylmethyl ester 

Relevant academic research and scientific papers

Enantioselective Synthesis of D-erythro-Sphingosine and of Ceramide

The enynol 2 was transformed into D-erythro-sphingosine 11 (7 steps, 46 percent) and into ceramide 1 (8 step, 41 percent overall yield).The key steps were the mono-epoxidation of the enynol 5 (Ti(t-BuO)4, (-)-D-diethyl tartrate, t-BuOOH) to 6 (86percent, >/= 98percent ee), the regioselective intramolecular opening of the oxirane 6 via the benzylurethane 7, and the reductive transformation of the acetylene 9 into the oxazolidinone 10 (Li, EtNH2, 88 percent).

ENANTIOSELECTIVE SYNTHESIS OF D-erythro-SPHINGOSINE

D-erythro-sphingosine (4) and the 3-amino-2-hydroxy L-erythro isomer 15 were synthesized in a highly enantio- and regioselective manner by a modified Sharpless asymmetric epoxidation.