84985-78-4

Usage

Uses

Used in Pharmaceutical Industry:
(3β,5Z,7R,8α,22E)-9,10-Secoergosta-5,10(19),22-triene-3,7,8-triol is used as an intermediate for the preparation of Vitamin-based antibiotics. Its unique structure allows it to serve as a key component in the synthesis of antibiotics that can potentially target specific pathogens or exhibit enhanced antimicrobial properties.
As a derivative of Vitamin D, (3β,5Z,7R,8α,22E)-9,10-Secoergosta-5,10(19),22-triene-3,7,8-triol may also find applications in other areas of pharmaceutical development, such as in the creation of drugs targeting specific diseases or conditions where Vitamin D plays a crucial role in treatment or management. Its chemical properties and structural features make it a promising candidate for further research and development in the pharmaceutical field.

InChI:InChI=1/C28H46O3/c1-18(2)19(3)8-9-21(5)24-12-13-25-27(24,6)14-7-15-28(25,31)26(30)17-22-16-23(29)11-10-20(22)4/h8-9,17-19,21,23-26,29-31H,4,7,10-16H2,1-3,5-6H3/b9-8+,22-17-/t19?,21-,23-,24-,25?,26?,27-,28?/m1/s1

Upstream product

• 50-14-6 Calciferol 

Downstream Products

• 100928-00-5 3β-O-(triisopropylsilyl)-7,8-dihydroxy-7,8-dihydrovitamin D2 
• 67337-15-9 <(1Z),(5S)>-2-<5-hydroxy-2-methylcyclohexylidene>-ethanol 
• 131852-63-6 (5Z,22E)-(7R)-3β-(tert-butyldimethylsilyloxy)-9,10-seco-8α-ergosta-5,10(19),22-triene-7,8-diol 
• 343969-43-7 Pyridine-2-carboxylic acid (R)-3-[(R)-2-hydroxy-2-[(1R,3aR,4R,7aR)-4-hydroxy-7a-methyl-1-((E)-(1R,4R)-1,4,5-trimethyl-hex-2-enyl)-octahydro-inden-4-yl]-eth-(Z)-ylidene]-4-methylene-cyclohexyl ester 
• 343969-42-6 (2Z)-[(3R,5S)-3,5-di-(tert-butyldimethylsilyloxy)-2-methylenecyclohexylidene]acetaldehyde 
• 338956-81-3 (Z,3R,5S)-[3,5-bis(tert-butyldimethylsilyl)oxy-2-methylenecyclohexylidene]ethanol 
• 343969-46-0 (1R,3aR,4R,7aR)-4-{(R)-2-[(3R,5S)-3-(tert-Butyl-dimethyl-silanyloxy)-5-hydroxy-2-methylene-cyclohex-(Z)-ylidene]-1-hydroxy-ethyl}-7a-methyl-1-((E)-(1R,4R)-1,4,5-trimethyl-hex-2-enyl)-octahydro-inden-4-ol 
• 343969-44-8 Pyridine-2-carboxylic acid (1S,3R)-3-hydroxy-5-[(R)-2-hydroxy-2-[(1R,3aR,4R,7aR)-4-hydroxy-7a-methyl-1-((E)-(1R,4R)-1,4,5-trimethyl-hex-2-enyl)-octahydro-inden-4-yl]-eth-(Z)-ylidene]-4-methylene-cyclohexyl ester 
• 343969-45-9 Pyridine-2-carboxylic acid (1S,3R)-3-(tert-butyl-dimethyl-silanyloxy)-5-[(R)-2-hydroxy-2-[(1R,3aR,4R,7aR)-4-hydroxy-7a-methyl-1-((E)-(1R,4R)-1,4,5-trimethyl-hex-2-enyl)-octahydro-inden-4-yl]-eth-(Z)-ylidene]-4-methylene-cyclohexyl ester 
• 343969-47-1 (1R,3aR,4R,7aR)-4-{(R)-2-[(3R,5S)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(Z)-ylidene]-1-hydroxy-ethyl}-7a-methyl-1-((E)-(1R,4R)-1,4,5-trimethyl-hex-2-enyl)-octahydro-inden-4-ol 
• 1104078-91-2 (5Z,22E,7R)-3β,7-di-(pent-4-enoyloxy)-9,10-seco-ergosta-5,10(19),22-triene-8β-ol 
• 55812-80-1 (1R,3aR,7aR)-7a-Methyl-1-((E)-(1R,4R)-1,4,5-trimethyl-hex-2-enyl)-octahydro-inden-4-one 

Relevant academic research and scientific papers

Synthesis of (17R)-17-methylincisterol, a highly degraded marine steroid

The synthesis of (17R)-17-methylincisterol, a highly degraded marine steroid, has been achieved starting from vitamin D2 in 8 steps and in 13% overall yield. Its O-demethyl analog, which is an intermediate in the synthetic sequence, is possibly

Vitamin D2 glycoside analogues as well as synthesis and application thereof

The invention discloses vitamin D2 glycoside analogues as well as a synthesis method and application thereof. The synthesis method comprises the steps of taking vitamin D2 as a raw material to prepare vitamin D2 glycoside analogues through an oxidation-re

Vitamin D modified based on amino acid2 Derivatives, synthesis and application

The invention discloses an amino acid modification based vitamin D2 derivative, synthesis and applications. Vitamin D2 fragment alcohol is prepared with the vitamin D2 serving as raw materials through redox reaction, and the amino acid modification based

Total synthesis of biologically active 20S-hydroxyvitamin D3

A total synthetic strategy of 20S-hydroxyVitamin D3 [20S-(OH)D3] involving modified synthesis of key intermediates 7 and 12, Grignard reaction to stereoselectively generate 20S-OH and Wittig-Horner coupling to establish D3 framework, was completed in 16 steps with an overall yield of 0.4%. The synthetic 20S-(OH)D3 activated Vitamin D receptor (VDR) and initiated the expression of downstream genes. In addition, 20S-(OH)D3 showed similar inhibitory potency as calcitriol [1,25(OH)2D3] on proliferation of melanoma cells.

Probing the structural requirements for vitamin D3 inhibition of the hedgehog signaling pathway

A structure-activity relationship study to elucidate the structural basis for hedgehog (Hh) signaling inhibition by vitamin D3 (VD3) was performed. Functional and non-functional regions of VD3 and VD2 were obtained through straightforward synthetic means

The first synthesis and biological testing of the enantiomer of 1α,25-dihydroxyvitamin D3

The 1α,25-dihydroxyvitamin D3 enantiomer was synthesized and examined in biological tests. The ring A precursor was prepared from vitamin D2 employing the Mitsunobu reaction for inversion of the configuration at C-3 and SeO2 hydroxylation at C-1. The CD rings-side chain portion was synthesized from an optically active hexanoic acid derivative using diastereoselective tandem Mukaiyama-Michael addition and vinylsulfone reduction as the key steps. The ring A and CD rings building blocks were combined using the Julia alkenylation reaction. 1α,25-Dihydroxyvitamin D3 enantiomer shows no significant affinity to the vitamin D receptor.

On the Julia Alkenylation reaction in vitamin D synthesis. Isolation of four geometrical isomers of vitamin D4

Coupling of sulfone 2 and aldehyde 3b using the Julia alkenylation procedure has been reexamined using modern product separation techniques. It was found that vitamin D4 1b and its geometric isomers 10, 11 and 12 are formed in a ratio of 75:10:10:5, respectively. The building blocks 2 and 3b were prepared from vitamin D2. Correlations for the structure assignment of vitamin D stereoisomers by 1H NMR spectroscopy are presented.

Synthesis and cytotoxic activity of steroid-anthraquinone hybrids

Synthesis of cytotoxic steroidal derivatives containing a quinone moiety is described. The synthetic strategy is based on an unusual A + CD → ABCD Diels-Alder approach which generates 9β-H cholestane analogs. The adducts formed are efficiently aromatized

Synthesis of Retiferol RAD1 and RAD2, the Lead Representatives of a New Class of des-CD Analogs of Cholecalciferol

The design and total convergent synthesis are described for the leading representatives of the new class of analogs of cholecalciferol with the CD-ring system replaced with a two-carbon aliphatic spacer.The leading representatives of C21 retiferols (RAD1