264872-32-4

Upstream product

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

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 
• 264872-34-6 4,5-anhydro-1-O-benzyl-2-deoxy-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 
• 264872-33-5 5-O-benzyl-1-chloro-1,4-dideoxy-D-threo-pentitol 

Relevant academic research and scientific papers

Palladium-catalyzed regio- and enantioselective fluorination of acyclic allylic halides

This report describes the Pd(0)-catalyzed fluorination of linear allylic chlorides and bromides, yielding branched allylic fluorides in high selectivity. Many of the significant synthetic limitations previously associated with the preparation of these products are overcome by this catalytic method. We also demonstrate that a chiral bisphosphine-ligated palladium catalyst enables highly enantioselective access to a class of branched allylic fluorides that can be readily diversified to valuable fluorinated products.

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.