278181-25-2

Upstream product

• 111-29-5 1 ,5-pentanediol 
• 69739-34-0 t-butyldimethylsiyl triflate 
• 131375-63-8 5-(4-methoxybenzyloxy)-1-pentanol 
• 131375-69-4 5-((4-methoxybenzyl)oxy)pentanal 
• 824-94-2 p-methoxybenzyl chloride 
• 278181-22-9 (S)-((2R,3R,4R,5S)-4,5-Bis-methoxymethoxy-3-methyl-6-oxo-tetrahydro-pyran-2-yl)-hydroxy-acetic acid ethyl ester 
• 278181-38-7 (S)-Hydroxy-((2R,3R,4R,5S,6S)-6-hydroxy-4,5-bis-methoxymethoxy-3-methyl-tetrahydro-pyran-2-yl)-acetic acid ethyl ester 
• 278181-09-2 (3S,4R)-3-methyl-8-[(p-methoxybenzyl)oxy]-4-[(triethylsilyl)oxy]octan-2-one 
• 278181-18-3 (2S,3R)-N-methoxy-N,2-dimethyl-7-[(p-methoxybenzyl)oxy]-3-[(triethylsilyl)oxy]heptanamide 
• 278181-10-5 (S)-(tert-Butyl-dimethyl-silanyloxy)-[(2R,3R,4R,5S,6R)-6-(tert-butyl-dimethyl-silanyloxy)-4,5-bis-methoxymethoxy-3-methyl-tetrahydro-pyran-2-yl]-acetaldehyde 
• 278181-23-0 (S)-(tert-Butyl-dimethyl-silanyloxy)-[(2R,3R,4R,5S,6R)-6-(tert-butyl-dimethyl-silanyloxy)-4,5-bis-methoxymethoxy-3-methyl-tetrahydro-pyran-2-yl]-acetic acid ethyl ester 
• 278181-11-6 (2'S,3'R,4S)-4-benzyl-N-{7-[(p-methoxybenzyl)oxy]-3-hydroxy-2-methylheptanoyl}-2-oxazolidinone 

Downstream Products

• 278181-26-3 acetic acid 1-{(tert-butyl-dimethyl-silanyloxy)-[6-(tert-butyl-dimethyl-silanyloxy)-4,5-bis-methoxymethoxy-3-methyl-tetrahydro-pyran-2-yl]-methyl}-9-(4-methoxy-benzyloxy)-4-methyl-3,5-bis-triethylsilanyloxy-nonyl ester 
• 278181-28-5 (1S,4S,5S,6R)-1-(tert-Butyl-dimethyl-silanyloxy)-1-[(2R,3R,4R,5S,6R)-6-(tert-butyl-dimethyl-silanyloxy)-4,5-bis-methoxymethoxy-3-methyl-tetrahydro-pyran-2-yl]-10-(4-methoxy-benzyloxy)-5-methyl-4,6-bis-triethylsilanyloxy-decan-2-one 
• 278181-40-1 (tert-butyl)dimethylsilyl 7-O-acetyl-4,8,10,12,13,14-hexadeoxy-2,3-O-bis-(methoxymethyl)-4,10-dimethyl-15-O-(p-methoxybenzyl)-6-O-[(tert-butyl)dimethylsilyl]-β-D-glycero-L-ido/l-talo-L-gluco-pentadecopyranoside 
• 278181-29-6 (2R,4S,5R,6R)-2-{(S)-(tert-Butyl-dimethyl-silanyloxy)-[(2R,3R,4R,5S,6R)-6-(tert-butyl-dimethyl-silanyloxy)-4,5-bis-methoxymethoxy-3-methyl-tetrahydro-pyran-2-yl]-methyl}-2-methoxy-6-[4-(4-methoxy-benzyloxy)-butyl]-5-methyl-tetrahydro-pyran-4-ol 
• 278181-30-9 Acetic acid (2R,4S,5S,6R)-2-[(S)-((2R,3R,4R,5S,6R)-6-acetoxy-4,5-bis-methoxymethoxy-3-methyl-tetrahydro-pyran-2-yl)-(tert-butyl-dimethyl-silanyloxy)-methyl]-2-methoxy-6-[4-(4-methoxy-benzyloxy)-butyl]-5-methyl-tetrahydro-pyran-4-yl ester 
• 278181-39-8 (tert-butyl)dimethylsilyl 7-O-acetyl-4,8,10,12,13,14-hexadeoxy-2,3-O-bis-(methoxymethyl)-4,10-dimethyl-15-O-(p-methoxybenzyl)-6-O-[(tert-butyl)dimethylsilyl]-β-D-galacto/β-D-gulo-L-gluco-pentadecopyranosid-9-ulose 

Relevant academic research and scientific papers

Synthesis of a C29-C51 subunit of spongistatin 1 (altohyrtin A) starting from (R)-3-benzyloxy-2-methylpropan-1-ol

A protected C29-C51 subunit ((+)-38) of spongistatin 1 has been obtained. Key steps involve the aldol condensation of (3S,4R)-3-methyl-7-[(p- methoxybenzyl)oxy]-4-[(triethylsilyl)oxy]octan-2-one ((-)-6) with (tert- butyl)dimethylsilyl 4-deoxy-2,3-di-O-(methoxymethyl)-4-methyl-6-O-(tert- butyl)dimethylsilyl)-β-D-glycero-L-gluco-heptodialdo-1,5-pyranoside ((+)-7) and a C-glycosidation of (4R,7RandS,E)-7,8-dichloro-2-methylidene-1- (trimethylsilyl)oct-5-en-4-yl p-methoxybenzoate (16). Aldehyde (+)-7 was derived from (R)-3-benzyloxy-2-methylpropan-1-ol ((+)-10) in 13 formal steps but requiring the isolation of five intermediate products only. The longest linear synthetic scheme converts (+)-10 into (+)-38 in 2% overall yield (isolation of 11 intermediate products).