220018-29-1

Upstream product

• 220018-27-9 (R)-1-((3-bromo-2-methylpropoxy)methyl)-4-methoxybenzene 
• 212051-35-9 (R)-methyl 3-((4-methoxybenzyl)oxy)-2-methylpropanoate 
• 89238-99-3 O-(4-methoxybenzyl)-trichloroacetimidate 
• 160238-45-9 (2S)-3-(4-methoxybenzyloxy)-2-methyl-1-propanol 
• 873-55-2 sodium benzenesulfonate 
• 183894-33-9 (R)-(+)-1-[(3'-iodo-2'-methylpropoxy)methyl]-4-methoxybenzene 
• 220018-28-0 (R)-1-(4-Methoxybenzyloxy)-2-methyl-3-phenylthiopropane 

Downstream Products

• 220018-30-4 (E)-(2R,7R)-3-Benzenesulfonyl-7-(tert-butyl-dimethyl-silanyloxy)-1-(4-methoxy-benzyloxy)-2,6-dimethyl-non-5-en-4-one 
• 220018-31-5 (E)-(2S,7R)-7-(tert-Butyl-dimethyl-silanyloxy)-1-(4-methoxy-benzyloxy)-2,6-dimethyl-non-5-en-4-one 
• 824982-87-8 (2R,3S,4S,5R)-1,6-bis(4-methoxybenzyloxy)-2,5-dimethylhexane-3,4-diol 
• 824982-88-9 (2R,5R)-4-Benzenesulfonyl-1,6-bis-(4-methoxy-benzyloxy)-2,5-dimethyl-hexan-3-ol 

Relevant academic research and scientific papers

Conformational analysis of axially substituted 4,4′-bi-1,3-dioxanyls

In contrast to the simple 4,4′-bi-1,3-dioxanyl derivative 6, which has no conformational preference at the inter-ring bond, the derivatives 9 and 10, which have two strategically placed axial methyl groups, show conformational preferences exceeding 95 %.

Approaches to a synthesis of galbonolide B

An approach to the C(7)-C(15) fragment of galbonolide B 2 has been completed in which the diene fragment 51 was assembled from (R)-3-tert-butyldimethylsilyloxypentan-2-one 29 by conversion into the unsaturated ester 30, acylation of the sulfone 47 using this ester, reductive desulfurisation, methylenation using a Wittig reaction and deprotection. Following model studies, the aldehyde 62, prepared by oxidation of the alcohol 51, was converted into a mixture of the epimeric alcohols 63 and these were converted into the di(methylene)tridecadienoic acid 65 using a phosphine catalysed Ireland-Claisen rearrangement. Sharpless epoxidations of the alcohol 67 using either L-(+)- or D-(-)-diethyl tartrate were highly stereoselective and gave the epoxides 68 and 69 which were clearly distinguishable. Model studies using the heptadiene monoepoxide 70 led to a synthesis of the monoprotected dihydroxy aldehyde 76 so establishing a protocol for the introduction into the vicinal diol of the galbonolides. Finally, aldol addition of tert-butyl acetate to the aldehyde 78 followed by selective protection, deprotection and cyclisation completed a synthesis of the macrolide 85.