452085-28-8

Upstream product

• 29117-54-2 (S)-(-)-1,2-pentanediol 
• 79364-35-5 (S)-1-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)but-3-en-1-ol 
• 117935-02-1 (S)-1-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-but-2-yn-1-ol 
• 167777-50-6 (2R,3S)-1,2-O-isopropylidene-(4E)-hexene-1,2,3-triol 
• 167777-51-7 (2R,3S)-1,2-O-isopropylidene-(4Z)-hexene-1,2,3-triol 
• 100791-67-1 (2R,3S)-1,2-O-isopropylidene-hexane-1,2,3-triol 
• 878632-87-2 (S)-2-Phenyl-4-propyl-[1,3]dioxolane 
• 100-52-7 benzaldehyde 
• 452085-27-7 (2R,3S)-3-O-benzylhexane-1,2,3-triol 
• 100-44-7 benzyl chloride 
• 100-39-0 benzyl bromide 

Downstream Products

• 167777-55-1 (S)-2-Benzyloxy-pentan-1-ol 
• 452085-31-3 (S)-1-[(2S,5R)-5-((1S,2S,3S)-3-{(2S,5R)-5-[(S)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-tetrahydro-furan-2-yl}-2-hydroxy-1-methyl-butyl)-tetrahydro-furan-2-yl]-pentan-2-ol 
• 452085-32-4 ((S)-2-{(2R,5S)-5-[(1R,2S,3R)-3-[(2R,5S)-5-((R)-2-Azido-pentyl)-tetrahydro-furan-2-yl]-2-(4-methoxy-benzyloxy)-1-methyl-butyl]-tetrahydro-furan-2-yl}-propoxy)-tert-butyl-diphenyl-silane 
• 452085-30-2 C₅₀H₇₈O₅Si₂ 
• 29117-54-2 (S)-(-)-1,2-pentanediol 

Relevant academic research and scientific papers

A stereocontrolled synthetic route to the C1-C18 subunit of pamamycin-607

The C1-C18 subunit 2 of the 16-membered macrodiolide pamamycin-607 has been synthesized stereoselectively using the Ag2CO3-mediated intramolecular iodoetherification for the two cis-2,5-disubstituted tetrahydrofurans, crotylation and cuprate epoxide opening for the hydroxyl and methyl substituents.

Total synthesis of (+)-pamamycin-607

Complete stereoselectivity was observed in the total synthesis of pamamycin-607 (1), which proceeded by iodoetherification of γ-triethylsilyloxyalkenes in the presence of an essential additive, silver carbonate, to provide the requisite three cis-2,5-disu

Synthesis of optically active β,γ-unsaturated α-amino acids of α,β-unsaturated γ-amino acids. S(N)2- vs. S(N)2'-dichotomy of the Mitsunobu amination of allylic alcohols

Novel and efficient syntheses (6-9 steps, overall yields 10-30%) are described for optically pure β,γ-unsaturated α-amino acids and α,β-unsaturated γ-amino acids, starting from (R)-isopropylidene glyceraldehyde and ethyl (S)-lactate, respectively. The key step is the Mitsunobu reaction of chiral secondary allylic alcohols with phthalimide as the nucleophile, where α,γ allylic transpositions are observed for the first time. The structure-α,γ-ratio-relationship is studied and also the stereochemistry of the allylic transposition. The α-substitution proceeds via clean S(N)2 inversion, whereas the γ-substitution corresponds to an (E)-anti attack of the nucleophilic with varying stereoselectivities.