753020-02-9

Upstream product

• 25636-49-1 3,3-dimethoxypentane 
• 96-22-0 pentan-3-one 
• 91326-83-9 (4S,5S)-dimethyl 2-phenyl-1,3-dioxolane-4,5-dicarboxylate 
• 84379-52-2 (2R,3R)-3-(benzyloxy)butane-1,2,4-triol 
• 753020-01-8 (R)-2-(benzyloxy)-2-[(R)-2,2-diethyl-1,3-dioxolan-4-yl]ethanol 

Downstream Products

• 850223-33-5 (R)-4-((E)-(R)-1-Benzyloxy-hexadec-2-enyl)-2,2-diethyl-[1,3]dioxolane 
• 753020-10-9 (3S,4S,5S)-3-N,N-dibenzylamino-4,5-dibenzyloxy-6-octadecyn-(1E)-enephosphonic acid 
• 753020-09-6 dimethyl (3S,4S,5S)-3-N,N-dibenzylamino-4,5-dibenzyloxy-6-octadecyn-(1E)-enephosphonate 
• 753020-08-5 (2S,3S,4S)-2-N,N-dibenzylamino-3,4-dibenzyloxy-5-octadecyn-1,3,4-triol 
• 1053626-17-7 (2R,3S,4S)-3,4-Bis-benzyloxy-2-dibenzylamino-octadec-5-ynal 
• 1054820-39-1 (R)-4-((1R,2S)-1,2-Bis-benzyloxy-hexadec-3-ynyl)-2,2-diethyl-[1,3]dioxolane 
• 753020-07-4 (2S,3S,4S)-2-azido-3,4-dibenzyloxy-5-octadecyn-1,3,4-triol 
• 1053714-00-3 (2S,3S,4S)-2-Amino-3,4-bis-benzyloxy-octadec-5-yn-1-ol 
• 753020-06-3 (2R,3R,4S)-3,4-dibenzyloxy-5-octadecyn-1,2,3,4-tetrol 
• 753020-11-0 (2R,3R,4S)-3-O-benzyl-1,2-O-(3'-pentylidene)-5-octadecyn-1,2,3,4-tetrol 
• 753020-04-1 (2R,3R)-3-O-benzyl-1,2-O-(3'-pentylidene)-4-oxo-5-octadecyn-1,2,3-triol 
• 851387-59-2 (2S,3R)-2-[octanoylamido]-3-O-benzyl-4-methylene-octadecane-1,3-diol 
• 851387-56-9 (2R,3S)-3-O-benzyl-4-oxo-1,2-O-(3'-pentylidene)-octadecane-1,2,3-triol 
• 851387-58-1 (2S,3R)-2-azido-3-O-benzyl-4-methylene-octadecane-1,3-diol 

Relevant academic research and scientific papers

Enantioselective construction of 6-substituted-α,β-unsaturated- δ-lactone: Total synthesis of anti-bacterial agent (-)-cleistenolide

An efficient and straightforward stereoselective synthesis of α,β-unsaturated lactone (1) cleistenolide is described. The synthesis was started from commercially available d-tartaric acid and completed within 13 steps with an overall yield of 7.92%. The cis-olefin was generated from Still-Gennari protocol and one of the hydroxyl groups was from dihydroxylation methodology. All the reactions were very clean and the products were obtained in very good yields.

Efficient and versatile synthesis of (2S,3R)-sphingosine and its 2-azido-3-O-benzylsphingosine analogue

The title compounds (1, 2) were synthesized from (2R,3S)-2-O-benzyl-3,4-O- (3′-pentylidene)-2,3,4-trihydroxybutanal (5). Installation of the E-double bond and aliphatic chain into the sphingosine base was effected by a sequence of Horner-Wadsworth-Emmons olefination of 5, conversion to allylic acetate 8, and copper-mediated Grignard coupling. The method is versatile, allowing a broad variety of aliphatic chains to be introduced in the organocuprate coupling step.

Synthesis of L-lyxo-phytosphingosine and its 1-phosphonate analogue using a threitol acetal synthon

The first synthesis of an isosteric phosphonate analogue of the aminotriol lipid phytosphingosine (3), together with an improved synthesis of (2S,3S,4S)-phytosphingosine (2), are described. A key intermediate is 3-pentylidene acetal 9, which was prepared in two steps from dimethyl 2,3-0-benzylidene-D-tartrate (7).