152386-85-1

Upstream product

• 152386-84-0 (2R,3R)-2-O-(4-methoxybenzyl)-1,2,3,4-butanetetrol 
• 96-22-0 pentan-3-one 
• 25636-49-1 3,3-dimethoxypentane 
• 2186-92-7 p-Anisaldehyde dimethyl acetal 
• 135972-13-3 (2S,3S)-2,3-O-(4-methoxybenzylidene)-diethyl tartrate 
• 152386-83-9 [(4R,5R)-5-Hydroxymethyl-2-(4-methoxy-phenyl)-[1,3]dioxolan-4-yl]-methanol 

Downstream Products

• 152386-87-3 (2S)-2-[(4R)-2,2-diethyl-[1,3]dioxolan-4-yl]-2-(4-methoxybenzyloxy)-acetaldehyde 
• 452082-48-3 5-[(S)-2-((R)-2,2-Diethyl-[1,3]dioxolan-4-yl)-2-(4-methoxy-benzyloxy)-ethylsulfanyl]-1-phenyl-1H-tetrazole 
• 247221-10-9 (3R)-3-[(4R)-2,2-diethyl-[1,3]dioxolan-4-yl]-3-(4-methoxybenzyloxy)propene 
• 247221-12-1 (3R)-3-[(4R)-2,2-diethyl-[1,3]dioxolan-4-yl]-3-(4-methoxybenzyloxy)propanal 
• 247221-11-0 (3R)-3-[(4R)-2,2-diethyl-[1,3]dioxolan-4-yl]-3-(4-methoxybenzyloxy)propan-1-ol 
• 247221-13-2 (4R)-4-phenylmethyl-3-[[(5R)-5-[(4R)-2,2-diethyl-[1,3]dioxolan-4-yl]]-(2R,3R)-3-hydroxy-5-(4-methoxybenzyloxy)-2-methyl-pentanoyl]-oxazolidin-2-one 
• 152386-90-8 Methanesulfonic acid (E)-(1R,2R)-1-(tert-butyl-dimethyl-silanyloxymethyl)-2-(4-methoxy-benzyloxy)-heptadec-3-enyl ester 
• 152386-91-9 (2S,3R,4E)-2-azido-1-tert-butyldimethylsilyloxy-3-(4-methoxybenzyl)-4-octadecen-3-ol 
• 152386-89-5 (2R,3R,4E)-1-tert-butyldimethylsilyloxy-3-(4-methoxybenzyl)-4-octadecen-2,3-diol 
• 152386-92-0 (2S,3R,4E)-2-azido-3-(4-methoxybenzyl)-4-octadecen-1,3-diol 
• 152386-88-4 (2R,3R,4E)-3-(4'-methoxybenzyloxy)-4-octadecene-1,2-diol 
• 452082-47-2 (2R,3S)-3-O-(4-methoxybenzyl)-1,2-O-(3-pentylidene)-4-(1-phenyl-1H-tetrazol-5-sulfonyl)-1,2,3-butantriol 
• 152386-86-2 (2R,3R,4E)-1,2-O-pentylidene-3-(4-methoxybenzyl)-4-octadecen-1,2,3-triol 
• 471923-95-2 (diethoxy-phosphoryl)-acetic acid 4-{6-[4,8-bis-(tert-butyl-dimethyl-silanyloxy)-6-methyl-octa-2,6-dienyl]-4-methylene-tetrahydro-pyran-2-yl}-1-[2-(3,4-dimethoxy-benzyloxy)-1-(4-methoxy-benzyloxy)-ethyl]-3-methyl-but-3-enyl ester 

Relevant academic research and scientific papers

An enantiospecific synthesis of D-erythro-sphingosine from D-tartaric acid

An efficient enantiospecific synthesis of D-erythro-sphingosine (1) via azidosphingosine (2) is described, the absolute stereochemistry being derived from D-tartaric acid.

An aldol approach to a building block corresponding to the C21-C26-part of FK506

Starting from D-tartrate 2, the chiral aldehyde 10 was prepared in 8 steps. Key steps include the reductive opening of the p-methoxybenzyl acetal 4 and the elongation of the aldehyde 7 via Wittig and hydroboration reaction providing the alcohol 9. Subsequent Evans aldol reaction provided compound 12 which corresponds to the C21-C26 part of the immunosuppressive FK506. Wiley-VCH Verlag GmbH, 1999.