316808-27-2

Upstream product

• 150-76-5 4-methoxy-phenol 
• 2211-94-1 4-methoxybenzyloxy ester of (S)-glycidol 
• 107-30-2 chloromethyl methyl ether 
• 796843-99-7 (R)-1-(4-Methoxy-phenoxy)-hex-5-en-2-ol 

Downstream Products

• 316808-34-1 2,2-Dimethyl-propionic acid (3S,5R,8R)-3,5,8-tris-methoxymethoxy-9-(4-methoxy-phenoxy)-nonyl ester 
• 316808-32-9 1-Methoxy-4-((2R,5R,7S)-2,5,7-tris-methoxymethoxy-dec-9-enyloxy)-benzene 
• 316808-30-7 (4S,6R,9R)-9-Methoxymethoxy-10-(4-methoxy-phenoxy)-dec-1-ene-4,6-diol 
• 316808-29-4 (4R,7R)-7-Methoxymethoxy-8-(4-methoxy-phenoxy)-oct-1-en-4-ol 
• 316808-28-3 (R)-4-Methoxymethoxy-5-(4-methoxy-phenoxy)-pentanal 

Relevant academic research and scientific papers

Enantioselective allyltitanation. Efficient synthesis of the C1-C14 polyol subunit of amphotericin B

(Matrix presented) An efficient synthesis of the C1-C14 fragment of amphotericin B is described. This synthesis is based on the formation of syn-1,3-diols from enantioselective allyltitanation of unprotected β-hydroxyaldehydes.

Homologation of protected hexoses with Grignard C1 reagents

Derivatives of three stereoisomeric hexodialdo-1,5-pyranosides were reacted with four Grignard C1 reagents: methoxymethyl-, allyloxymethyl-, benzyloxymethyl, and dimethylphenylsilylmethyl-magnesium chlorides. Two stereoisomeric heptoses were obtained in each case in a good yield. The methyl alloside-derived heptosides were accompanied by C-5 inverted products. The addition of Grignard reagents to aldehydes 5-8 has been discussed in terms of parallel α- or β-chelated and Felkin-Anh transition states. It has been found that the silyl Grignard reagent 12 exhibits a strong preference for the formation of heptose derivatives of L-configuration at C-6. (C) 2000 Elsevier Science Ltd.