199658-06-5

Upstream product

• 199658-05-4 (2E)-4-[(4-methoxybenzyl)oxy]but-2-en-1-ol 
• 824-94-2 p-methoxybenzyl chloride 
• 2746-25-0 p-Methoxybenzyl bromide 
• 863222-51-9 4-(4-methoxybenzyloxy)-2-butynal 
• 4039-83-2 3-(4-methoxybenzyloxy)propyne 
• 207795-41-3 ethyl 4-(4-methoxybenzyloxy)but-2-ynoate 
• 145222-40-8 4-(p-methoxybenzyloxy)-1-hydroxy-2-butyne 

Downstream Products

• 887612-04-6 (2R,3R)-4-(4-Methoxy-benzyloxy)-2-methyl-butane-1,3-diol 
• 1204484-49-0 (2R,3R)-4-(4-methoxybenzyloxy)-2-azidobutane-1,3-diol 
• 1354396-58-9 (2R,3S)-3-(((4-methoxybenzyl)oxy)methyl)oxirane-2-carbaldehyde 

Relevant academic research and scientific papers

Formal synthesis of borrelidin: A highly enantio- and diastereoselective access to the Morken's C2-C12 intermediate

In contrast to methyl and isobutyl phenyl sulfone, condensing under basic conditions higher alkyl sulfones and trans-2,3-epoxy-butanol 13c (or its O-benzyl and O-silyl derivatives) proved unfeasible, a difficulty that was overcome by using mono ethers of trans-2,3-epoxy-butane-1,4-diol 35c as the electrophilic reagents. Thus, adding excess BuLi to a mixture of the benzyl ether 35b and sulfone ent-12a, a stereodiad sulfone prepared in pure state from the R-Roche ester, via the O-trityloxy-sulfone ent-12c (X-ray), gave, after elimination by column chromatography of the side-formed regioisomer, a diolsulfone that was next converted to sulfone 20 by means of conventional functional-group modifications. Reacting like-wise this sulfone with the parent O-PMB derivative 35a, and then proceeding to the same purification process and function adjustment, delivered the title fragment in virtually pure state.

Attempts towards the synthesis of mupirocin-H

The stereoselective synthesis of segments C1-C6 (3), C7-C12 (4) of mupirocin-H has been achieved. The synthetic procedure for the C1-C6 segment includes the zinc mediated allyl Grignard reaction with Rglyceraldehyde, Swern oxidation/Witting olefination reactions and followed by Sharpless asymmetric epoxidation. The C7-C12 segment was synthesized using again Sharpless asymmetric epoxidation on mono PMB protected 2-butene-1,4-diol, followed by regioselective opening of this epoxide with trimethyl aluminium. Both segments C1-C6 (3) and C7-C12 (4) possesses the five new stereogenic centers along with trans-olefin, but in various attempts condensation of 3 and 4 segments to give C-C bond forming parent segment (2) not affirmed, hence this work constitutes the synthesis of fragments C1-C6 (3) and C7-C12 (4) of mupirocin-H. {figure presented}

Stereoselective Synthesis of Isochromanones by an Asymmetric Ortho-Lithiation Strategy: Synthetic Access to the Isochromanone Core of the Ajudazols

Full details on the design, development, and application of a highly stereoselective strategy for the synthesis of isochromanones are reported. The method is based on an asymmetric ortho lithiation with aldehyde electrophiles and utilizes the chiral memor

Catalytic diastereoselective reduction of α,β-epoxy and α,β-aziridinyl ynones

The Noyori transfer hydrogenation of α,β-epoxy and α,β-aziridinyl ynones leads to the corresponding α,β-epoxy or α,β-aziridinyl propargylic alcohols with high reagent-controlled diastereoselectivity.

Asymmetric synthesis of triacetyl-d-erythro-sphingosine and D-1-deoxyallonojirimycin via Miyashita C2 selective endo-mode azide opening of 2,3-epoxy alcohol

An efficient protocol for the asymmetric synthesis of triacetyl-d-erythro-sphingosine and D-1-deoxyallonojirimycin has been developed starting from commercially available propargyl alcohol. The key steps involved Sharpless asymmetric epoxidation and Miyashita C2 selective endo-mode azide opening of the 2,3-epoxy alcohol.

Enantioselective total synthesis of bistramide A

The enantioselective synthesis of bistramide A has been achieved with a longest linear sequence of 18 steps. The synthetic strategy involves the use of a distereoselective glycolate alkylation, an aldol addition of a chlorotitanium enolate of N-acylthiazolidinthione, and a Sharpless asymmetric epoxidation to synthesize the three key fragments. Copyright

Synthesis of the EF-ring segment of ciguatoxin CTX1B based on novel regioselective reduction of unsaturated cyanohydrins and ring-closing olefin metathesis

Aiming at a convergent total synthesis of ciguatoxin CTX1B, its EF-ring segment has been synthesized. During the synthesis, a novel method for the construction of branched ethers, based on regioselective reduction of γ-alkoxy β,γ-unsaturated α-silyloxy ni

Stereospecific synthesis of α,ω-cis- and α,ω-trans-disubstituted oxepanes

An efficient and versatile method for the stereospecific construction of α,ω-cis- and α,ω-trans-disubstituted oxepane skeletons is described. Cyclization of the hydroxy epoxides promoted by a (Bu3Sn)2O/ Zn(OTf)2 system proceeded via an S(N)2 process and exo mode selectivity regardless of the configuration of the hydroxyl and the epoxy groups to provide the corresponding oxepanes in excellent yields. (C) 2000 Elsevier Science Ltd.