159751-61-8

Upstream product

• 102518-03-6 (R)-(+)-3-<(benzyloxy)methoxy>-2-methylpropanol 
• 159751-60-7 Toluene-4-sulfonic acid (S)-3-benzyloxymethoxy-2-methyl-propyl ester 
• 116021-11-5 (S)-(+)-(benzyloxy)methyl 3-<(benzyloxy)methoxy>-2-methylpropionate 

Downstream Products

• 159751-62-9 (R)-5-Benzyloxymethoxy-2,2,4-trimethyl-pentanoic acid ethyl ester 
• 900159-57-1 {(R)-1-[2-((R)-3-Benzyloxymethoxy-2-methyl-propyl)-[1,3]dithian-2-ylmethyl]-butoxy}-tert-butyl-dimethyl-silane 
• 900159-58-2 (2R,6R)-1-Benzyloxymethoxy-6-(tert-butyl-dimethyl-silanyloxy)-2-methyl-nonan-4-one 
• 900159-59-3 [3-(3-benzyloxymethoxy-2-methyl-propyl)-1-propyl-but-3-enyloxy]-tert-butyl-dimethyl-silane 

Relevant academic research and scientific papers

Stereocontrolled and convergent total synthesis of amphidinolide T3

Stereocontrolled and convergent total synthesis of amphidinolide T3 has been described. A retrosynthetic scheme was constructed that led to the recognition of readily available and enantiomerically related compounds as starting materials for the total synthesis of amphidinolide T3. Thus, the two key building blocks 6 and 7 were defined as subtargets and synthesized in optically active forms. The C1-C12 fragment 6 was derived from commercially available D-glutamic acid or its synthetically equivalent (R)-5- hydroxymethyltetrahydrofuran-2-one 16 as starting material involving highly diastereoselective asymmetric allylation as a key step. The C13-C21 fragment 7 was efficiently synthesized in high yield through the dithiane coupling of the segment 10 and iodide 11, followed by subsequent deprotection and Petasis olefination. Eventually, assembly of the fragment aldehyde 6 and dithiane 7 along with C-C bond formation, a two-step oxidation-reduction sequence, selective macrolactonization, and functional transformation furnished the convergent total and formal synthesis of amphidinolide T3 and T4, and this approach also provides a flexible and practical synthesis of amphidinolide T macrolides.

Synthetic study on oscillatoxin D: Construction of the C1-C26 spiroether segment by intramolecular aldol condensation and Michael-type addition

The C1-C7 segment (10) and the C8-C21 segment (14) of oscillatoxin D have been synthesized efficiently. The acyclic compound obtained by coupling of these two segments, has been converted into the C1-C26 spiroether (18) possessing the same stereogenic centers of oscillatoxin D. The construction of the spiroether has been achieved by intramolecular aldol condensation and Michael-type addition as key steps.