264872-33-5

Upstream product

• 89923-31-9 (E)-5-(benzyloxy)pent-2-en-1-ol 
• 100-39-0 benzyl bromide 
• 22273-77-4 ((but-3-yn-1-yloxy)methyl)benzene 
• 264872-32-4 (E)-(((5-chloropent-3-en-1-yl)oxy)methyl)benzene 

Downstream Products

• 264872-39-1 5-O-benzyl-2-[(tert-butoxycarbonyl)(methyl)amino]-1,2,4-trideoxy-3-O-(methoxymethyl)-1-phenyl-D-threo-pentitol 
• 264872-38-0 5-O-benzyl-2-[(tert-butoxycarbonyl)amino]-1,2,4-trideoxy-3-O-(methoxymethyl)-1-phenyl-D-threo-pentitol 
• 264872-37-9 2-amino-5-O-benzyl-1,2,4-trideoxy-3-O-(methoxymethyl)-1-phenyl-D-threo-pentitol 
• 264872-36-8 5-O-benzyl-1,4-dideoxy-3-O-(methoxymethyl)-1-phenyl-D-threo-pentitol 
• 264872-43-7 C₂₀H₂₄O₃ 
• 264872-35-7 4,5-anhydro-1-O-benzyl-2-deoxy-3-O-(methoxymethyl)-D-threo-pentitol 
• 229981-04-8 (3R,4S)-4--3-(methoxymethoxy)-5-phenylpentanoic acid 
• 229981-25-3 (3R,4S)-4--3-(methoxymethoxy)-1-hydroxy-5-phenylpentane 
• 264872-34-6 4,5-anhydro-1-O-benzyl-2-deoxy-D-threo-pentitol 

Relevant academic research and scientific papers

Primary and secondary allyltitanium(IV) reagents in aldehyde allylation II: Application to an enantioselective preparation of a C1-C7 fragment of spiramycin

A synthetic approach to the eastern part of spiramycin, an important antibiotic compound, is described. Introduction of the side chain was first envisaged through a Hoppe aldehyde allylation. This reaction was carried out between an optically pure aldehyde 32 and a (±)-γ-alkoxy allyltitanium(IV) species derived from a primary γ-alkoxy allyl (diisopropyl)carbamate. Under kinetic resolution conditions, the anti-Cram compound 35 was obtained in an 80:20 mixture, with the Cram isomer 34, in 81% yield. Employing the optically pure (S)-γ-alkoxy allyl (diisopropyl)carbamate 36, the corresponding (R)-γ-alkoxy allyltitanium (R)-'Ti'-III was generated under n-BuLi·TMEDA/Ti(Oi-Pr)4 conditions, that reacted with aldehyde 32 in double stereodifferentiation to deliver the expected Cram compound 40 in 80% yield (95% de). This latter corresponded to the C1-C7 fragment of spiramycin.

Synthesis of the γ-amino-β-hydroxy acid of hapalosin via an asymmetric dihydroxylation route

Starting from the allylic alcohol 3, the epoxide 7 was prepared by asymmetric dihydroxylation of the allylic chloride followed by subsequent protection of the secondary hydroxy group. Opening of the oxirane with phenyl cuprate gave the triol 8 with a free hydroxy group. Mitsunobu reaction of 8 with diphenylphosphoryl azide led to the azide 9. Simple functional group manipulations delivered the acid 2 in further five steps. (C) 2000 Elsevier Science Ltd.