120040-77-9

Upstream product

• 121964-06-5 (2R,3S,4S)-3-O-Benzyl-1,2-O-isopropylidene-4-methylpentane-1,2,3,5-tetrol 
• 22323-80-4 (4S)-2,2-dimethyl-[1,3]dioxolane-4-carbaldehyde 
• 120143-04-6 (3S,4S,5S)-4-hydroxy-5,6-(isopropylidenedioxy)-3-methylhex-1-ene 
• 74889-58-0 Methyl 3,4-O-isopropylidene-2-O-(methoxaloyl)-L-threonate 
• 114185-09-0 (2S,3R)-1,2-isopropylidenedioxy-butan-3,4-diol 
• 58650-93-4 2,3-O-bis-methyl-5,6-O-isopropylidene-L-ascorbic acid 
• 120143-05-7 (3S,4S,5S)-4-(benzyloxy)-5,6-(isopropylidenedioxy)-3-methylhex-1-ene 
• 100572-69-8 (2R,3S,4S)-3-Bnzyloxy-1,2-O-isopropylidene-4-methyl-5-hexene-1,2-diol 

Downstream Products

• 1078119-22-8 C₂₀H₂₉NO₅ 
• 1078118-70-3 C₂₀H₂₉NO₅ 
• 146518-11-8 (1S,2S,4aS,5R,6R,7S,8R,8aR)-5-Benzyloxy-2-[(E)-3-(tert-butyl-dimethyl-silanyloxy)-1-methyl-propenyl]-7-(imidazole-1-carbothioyloxy)-1,6,8-trimethyl-1,2,4a,5,6,7,8,8a-octahydro-naphthalene-1-carboxylic acid methyl ester 
• 146518-14-1 (1S,2S,4aS,5R,6S,7R,8R,8aR)-5-Benzyloxy-2-[(E)-3-(tert-butyl-dimethyl-silanyloxy)-1-methyl-propenyl]-7-hydroxy-1,6,8-trimethyl-1,2,4a,5,6,7,8,8a-octahydro-naphthalene-1-carboxylic acid methyl ester 
• 146566-81-6 methyl (E,Z,E,E)-(4S,5S,6S,7S)-5-acetoxy-7-(benzyloxy)-9-bromo-14-hydroxy-2,4,6,12-tetramethyltetradeca-2,8,10,12-tetraenoate 
• 146518-03-8 (1S,2S,4aS,5S,6R,7R,8R,8aR)-7-Acetoxy-5-benzyloxy-4-bromo-2-((E)-3-hydroxy-1-methyl-propenyl)-1,6,8-trimethyl-1,2,4a,5,6,7,8,8a-octahydro-naphthalene-1-carboxylic acid methyl ester 
• 146518-06-1 (1S,2S,4aS,5R,6R,7S,8R,8aR)-7-Acetoxy-5-benzyloxy-2-((E)-3-hydroxy-1-methyl-propenyl)-1,6,8-trimethyl-1,2,4a,5,6,7,8,8a-octahydro-naphthalene-1-carboxylic acid methyl ester 
• 120040-80-4 methyl (E)-(4S,5R,6S,7S,8S)-5-acetoxy-7-(benzyloxy)-8,9-(isopropylidenedioxy)-2,4,6-trimethylnon-2-enoate 
• 146518-02-7 methyl (E)-(4S,5S,6S,7S,8S)-5-acetoxy-7-(benzyloxy)-8,9-(isopropylidenedioxy)-2,4,6-trimethylnon-2-enoate 
• 146608-29-9 methyl (E)-(4S,5S,6S,7S)-5-acetoxy-7-(benzyloxy)-9,9-dibromo-2,4,6-trimethylnona-2,8-dienoate 
• 146518-13-0 (1S,2S,4aS,5R,6S,7R,8R,8aR)-5-Benzyloxy-7-hydroxy-2-((E)-3-hydroxy-1-methyl-propenyl)-1,6,8-trimethyl-1,2,4a,5,6,7,8,8a-octahydro-naphthalene-1-carboxylic acid methyl ester 
• 120040-86-0 methyl 2β-<(E)-3-hydroxy-1-methylprop-1-enyl>-5α-(benzyloxy)-7α-hydroxy-1α,6α,8β-trimethyl-1,2,4aα,5,6,7,8,8aβ-octahydronaphthalene-1β-carboxylate 
• 146517-98-8 methyl (E)-(4S,5R,6S,7S,8S)-5-acetoxy-7-(benzyloxy)-8,9-dihydroxy-2,4,6-trimethylnon-2-enoate 
• 146518-12-9 (E)-(4R,5R,6S,7S,8S)-5-Acetoxy-7-benzyloxy-8,9-dihydroxy-2,4,6-trimethyl-non-2-enoic acid methyl ester 

Relevant academic research and scientific papers

Epoxyamide-based strategy for the synthesis of polypropionate-type frameworks

(Chemical Equation Presented) A new approach to the stereoselective synthesis of polypropionate-type frameworks is reported utilizing reactions of amide-stabilized sulfur ylides with chiral aldehydes. To establish a new strategy for macrolide fragment synthesis, the stereoselectivity of these reactions in the construction of epoxy amides was the most important aspect of this study. In this aspect, we found a strong influence of the protecting groups employed in the starting aldehydes upon the stereochemical outcome of their reactions with the sulfur ylide 1. Thus, numerous aldehydes showed remarkable stereofacial differentiation, providing a major diastereoisomer, in contrast to others that displayed a poor or no stereoselectivity. Despite the difficulties encountered for some cases with respect to their diastereomeric yields, we were able to prepare various stereotetrads and stereopentads, thus enhancing the synthetic value of this new methodology for the preparation of typical polypropionate frameworks found in many natural products, in particular the macrolide class of antibiotics.

Application of the steric directing group strategy to the stereoselective synthesis of the octahydronaphthalene substructure of kijanolide and tetronolide

A highly stereoselective synthesis of the kijanolide/tetronolide octahydronaphthalene substructure 4 has been completed. The synthesis proceeds in 16 steps from L-glyceraldehyde acetonide (8), with 88% stereoselectivity and in 11% overall yield. Key steps are the following: (1) the asymmetric crotylborations of 8 and 12 that introduce the C(5), C(6), and C(8) stereocenters of 4; (2) the modified Suzuki coupling of vinylboronic acid 36 and dibromo olefin 31 that establishes the conjugated triene unit and introduces the C(9) Br steric directing group in a single operation; and (3) the highly stereoselective intramolecular Diels-Alder cycloaddition of tetraene 7. Stereochemical information obtained from the intramolecular Diels-Alder reactions of 25 and 26 provides a framework for rationalizing the role of the C(5) acetoxy group and the C(9) Br substituent on the stereoselectivity of the intramolecular Diels-Alder reaction of 7.

Highly Felkin-Anh Selective Hiyama Additions of Chiral Allylic Bromides to Aldehydes. Application to the First Synthesis of Nephromopsinic Acid and Its Enantiomer

The chromium(II)-mediated addition ("Hiyama reaction") of the chiral allylic bromides 13, 15, 19, 22, 24, and 27 to achiral and chiral aldehydes proceeds with high Felkin-Anh selectivity with respect to the stereocenter at Cγ in the bromide (Table II). By