152386-83-9

Upstream product

• 135972-13-3 (2S,3S)-2,3-O-(4-methoxybenzylidene)-diethyl tartrate 
• 13171-64-7 Dimethyl D-tartrate 
• 123-11-5 4-methoxy-benzaldehyde 
• 2186-92-7 p-Anisaldehyde dimethyl acetal 

Downstream Products

• 866454-44-6 (2R)-3-[(tert-butyldiphenylsilyl)oxy]-2-(4-methoxybenzyloxy)propanal 
• 880344-83-2 (2R,3S)-1-(tert-Butyl-diphenyl-silanyloxy)-2-(4-methoxy-benzyloxy)-hex-5-en-3-ol 
• 880344-82-1 (2R,3R)-4-(tert-Butyl-diphenyl-silanyloxy)-3-(4-methoxy-benzyloxy)-butane-1,2-diol 
• 880344-84-3 Acrylic acid (S)-1-[(R)-2-(tert-butyl-diphenyl-silanyloxy)-1-(4-methoxy-benzyloxy)-ethyl]-but-3-enyl ester 
• 343782-89-8 (S)-(4-Methoxy-benzyloxy)-((2S,4R)-4-methyl-6-oxo-tetrahydro-pyran-2-yl)-acetaldehyde 
• 343783-00-6 (4R,6S)-6-[(R)-2-Hydroxy-1-(4-methoxy-benzyloxy)-ethyl]-4-methyl-tetrahydro-pyran-2-one 
• 343782-87-6 (S)-6-[(R)-2-(tert-Butyl-diphenyl-silanyloxy)-1-(4-methoxy-benzyloxy)-ethyl]-5,6-dihydro-pyran-2-one 
• 343782-88-7 (4R,6S)-6-[(R)-2-(tert-Butyl-diphenyl-silanyloxy)-1-(4-methoxy-benzyloxy)-ethyl]-4-methyl-tetrahydro-pyran-2-one 
• 343782-90-1 (4R,6S)-6-[(1R,2R,5R,7S)-8-Azido-2-hydroxy-1-(4-methoxy-benzyloxy)-5,7-dimethyl-4-oxo-octyl]-4-methyl-tetrahydro-pyran-2-one 
• 343783-01-7 Benzoic acid (1R,4R,6S)-7-azido-1-[(S)-(4-methoxy-benzyloxy)-((2S,4R)-4-methyl-6-oxo-tetrahydro-pyran-2-yl)-methyl]-4,6-dimethyl-3-oxo-heptyl ester 
• 1239889-47-4 C₂₄H₄₄O₅Si₂ 
• 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 

Relevant academic research and scientific papers

Synthesis and disproof of the structure proposed for the tetrahydrofuranol isolated from Michelia compressa var. lanyuensis (Magnoliaceae)

The previously proposed structure for a tetrahydrofuranol isolated from the leaves of Michelia compressa var. lanyuensis (Magnoliaceae) was synthesised in an enantiopure form using diethyl D-tartarate as the starting material. The synthetic sample showed spectroscopic data incompatible with those for the natural product and thus unequivocally disproved the previously assigned structure.

Synthesis of the FG ring fragment of pectenotoxins 1-9

The synthesis of the FG ring fragment common to pectenotoxins 1-9 is reported.The successful, convergent synthesis relied on high yielding routes to access two key intermediates; aldehyde 1 and phosphonium salt 2.A Z-selective Wittig reaction gave access

Asymmetric synthesis of the cyclopentanones related to NCS and N1999A2 antitumor antibiotics

Optically pure protected mono- or dihydroxylated cyclopentanones, precursors for the core of the antitumor antibiotics NCS and N1999A2, 1 and 2, were obtained in six to eight steps with excellent overall yields (up to 52%).

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.

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.