88255-83-8

Upstream product

• 23477-88-5 (+/-)-(1R*,3R*,4R*)-3,4-dihydroxycyclohexanecarboxylic acid 
• 52892-14-5 (1S,3R)-7-Oxa-bicyclo[4.1.0]heptane-3-carboxylic acid 
• 4771-80-6 1,2,5,6-tetrahydrobenzoic acid 

Downstream Products

• 23477-88-5 (+/-)-(1R*,3R*,4R*)-3,4-dihydroxycyclohexanecarboxylic acid 
• 116386-61-9 (1R,3R,4R)-3-Methoxy-4-triisopropylsilanyloxy-cyclohexanecarbaldehyde 
• 126788-82-7 (S)-4-Benzyl-3-[(E)-(2S,3R,4R,5S)-2-chloro-3-hydroxy-7-((1R,3R,4R)-3-methoxy-4-triisopropylsilanyloxy-cyclohexyl)-4,6-dimethyl-5-triethylsilanyloxy-hept-6-enoyl]-oxazolidin-2-one 
• 126788-83-8 (S)-4-Benzyl-3-[(E)-(3S,4R,5S)-3-hydroxy-7-((1R,3R,4R)-3-methoxy-4-triisopropylsilanyloxy-cyclohexyl)-4,6-dimethyl-5-triethylsilanyloxy-hept-6-enoyl]-oxazolidin-2-one 
• 126788-85-0 (E)-(3S,4R,5S)-7-((1R,3R,4R)-3-Methoxy-4-triisopropylsilanyloxy-cyclohexyl)-4,6-dimethyl-5-triethylsilanyloxy-3-triisopropylsilanyloxy-hept-6-enoic acid methoxy-methyl-amide 
• 116386-67-5 (E)-(3S,4R,5S)-7-((1R,3R,4R)-3-Methoxy-4-triisopropylsilanyloxy-cyclohexyl)-4,6-dimethyl-5-triethylsilanyloxy-3-triisopropylsilanyloxy-hept-6-enal 
• 126788-79-2 (S)-4-Benzyl-3-[(E)-3-hydroxy-5-(3-methoxy-4-triisopropylsilanyloxy-cyclohexyl)-2,4-dimethyl-pent-4-enoyl]-oxazolidin-2-one 
• 126788-84-9 (E)-(3S,4R,5S)-3-Hydroxy-7-((1R,3R,4R)-3-methoxy-4-triisopropylsilanyloxy-cyclohexyl)-4,6-dimethyl-5-triethylsilanyloxy-hept-6-enoic acid methoxy-methyl-amide 
• 126788-81-6 (E)-(2S,3S)-5-((1R,3R,4R)-3-Methoxy-4-triisopropylsilanyloxy-cyclohexyl)-2,4-dimethyl-3-triethylsilanyloxy-pent-4-enoic acid methoxy-methyl-amide 
• 116386-65-3 (E)-(2S,3S)-5-((1R,3R,4R)-3-Methoxy-4-triisopropylsilanyloxy-cyclohexyl)-2,4-dimethyl-3-triethylsilanyloxy-pent-4-enal 
• 126788-80-5 (E)-(2S,3S)-3-Hydroxy-5-((1R,3R,4R)-3-methoxy-4-triisopropylsilanyloxy-cyclohexyl)-2,4-dimethyl-pent-4-enoic acid methoxy-methyl-amide 
• 126788-77-0 (1R,3R,4R)-3-Methoxy-4-triisopropylsilanyloxy-cyclohexanecarboxylic acid methoxy-methyl-amide 
• 116386-60-8 (1R,3R,4R)-3-Hydroxy-4-triisopropylsilanyloxy-cyclohexanecarboxylic acid methoxy-methyl-amide 
• 116386-63-1 (E)-3-((1R,3R,4R)-3-Methoxy-4-triisopropylsilanyloxy-cyclohexyl)-2-methyl-propenal 

Relevant academic research and scientific papers

NOVEL COMPOUNDS

Novel rapamycin analogues and methods for their production with FKBP and/or MIP inhibitory activity with reduced mTOR inhibitory activity with therapeutic potential e.g. as bacterial virulence inhibitors.

PRODUCTION OF POLYKETIDES AND OTHER NATURAL PRODUCTS

The present invention relates to production of polyketides and other natural products and to libraries of compounds and individual novel compounds. Therefore in one aspect the present invention provides 17-desmethylrapamycin and analogues thereof, methods for their production, including recombinant strains, and isolation and uses of the compounds of the invention. In a further aspect the present invention provides for the use of 17-desmethylrapamycin and analogues thereof in the induction or maintenance of immunosuppression, the stimulation of neuronal regeneration or the treatment of cancer, B-cell malignancies, fungal infections, transplantation rejection, graft vs. host disease, autoimmune disorders, diseases of inflammation vascular disease and fibrotic diseases, and in the regulation of wound healing.

Application of chemical P-450 model systems to studies on drug metabolism. Part X. Novel hydroxylactonization of γ,δ- and β,γ-unsaturated carboxylic acids with an iron porphyrin-iodosylbenzene system

The oxidative hydroxylactonization of γ,δ- and β,γ-unsaturated carboxylic acids by a chemical cytochrome P-450 model and rat liver microsomal systems has been investigated. In the chemical system using meso-tetrakis(2,6-dichlorophenyl)porphyrin iron chloride [Fe(TDClPP)Cl] with iodosylbenzene (PhIO), γ,δ-unsaturated carboxylic acids have been converted into δ-hydroxy-γ-lactones in high yield and with high stereoselectivity. As an example of a β,γ-unsaturated carboxylic acid, indomethacin has been converted into the corresponding β-hydroxy γ-lactone. Several experiments directed toward mechanistic elucidation of the lactonization exclude a mechanism occurring via an epoxide intermediate. The products have been used as standards to identify the metabolites in the microsomal oxidation. In the case of indomethacin, the γ-lactone form is detected as a metabolite in the rat liver microsomal system, in a yield of 1.33%; the yield is significantly decreased in the presence of 2-diethylaminoethyl-2,2-diphenylvalerate hydrochloride (SKF-525A) and under a mixed CO-O2 (4:1) atmosphere. Thus, these metabolites are considered to be formed by a cytochrome P-450-dependent reaction.

Chemistry of tricarbonyl hemiketals and application of Evans' technology to the total synthesis of the immunosuppressant (-)-FK-506

Details of model studies probing the chemistry of the tricarbonyl region of FK-506 are presented, and their use in designing a successful route to this immunosuppressant is outlined. Application of asymmetric oxazolidinone alkylation/aldol methodology to a convergent, highly flexible synthesis of the C10-C18 fragment and to improvements in the preparation of the C20-C34 segment are also discussed.