272776-87-1

Basic information

• Product Name: 3-epi-24R 25-Dihydroxy VitaMin D3
• Synonyms: 3-epi-24R 25-Dihydroxy VitaMin D3
• CAS NO: 272776-87-1
• Molecular Formula: C27H44O3
• Molecular Weight: 416.63646
• Product Categories: Chiral Reagents, Metabolites & Impurities, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 272776-87-1.mol

Chemical Properties

• Boiling Point: 571.1±35.0 °C(Predicted)
• Appearance: /
• Density: 1.06±0.1 g/cm3(Predicted)
• PKA: 14.67±0.29(Predicted)
• CAS DataBase Reference: 3-epi-24R 25-Dihydroxy VitaMin D3(CAS DataBase Reference)
• NIST Chemistry Reference: 3-epi-24R 25-Dihydroxy VitaMin D3(272776-87-1)
• EPA Substance Registry System: 3-epi-24R 25-Dihydroxy VitaMin D3(272776-87-1)

Safety Data

• Hazardous Substances Data: 272776-87-1(Hazardous Substances Data)

Usage

Uses

3-epi-24R 25-Dihydroxy Vitamin D3 is the hydroxylated metabolite of Vitamin D3 (V676045).

Upstream product

• 60103-15-3 24(S),25-Dihydroxycholesterol 
• 60103-14-2 (24R)-3β,24,25-Trihydroxy-cholest-5-ene 
• 474432-42-3 (3β,5Z,7E,24S)-3-[(tert-butyldimethylsilyl)oxy]-9,10-secocholesta-5,7,10(19)-triene-24,25-diol cyclic 24,25-(1-methylethylidene acetal) 
• 474432-40-1 (24S)-de-A,B-24,25-dihydroxycholestan-8-one cyclic 24,25-(1-methylethylidene acetal) 
• 239100-44-8 (8β,24S)-de-A,B-cholesta-8,24,25-triol cyclic 24,25-(1-methylethylidene acetal) 
• 239100-43-7 (1R,3aR,4S,7aR)-1-[(1R,4S)-4,5-dihydroxy-1,5-dimethylhexyl]-7a-methyl-octahydro-1H-inden-4-ol 
• 113278-72-1 (R)-2-((1aR,3aR,3bS,5aS,6R,8aS,8bS,10R,10aR)-10-Methoxy-3a,5a-dimethyl-hexadecahydro-cyclopenta[a]cyclopropa[2,3]cyclopenta[1,2-f]naphthalen-6-yl)-4-((R)-2,2,5,5-tetramethyl-[1,3]dioxolan-4-yl)-butan-1-ol 
• 74348-77-9 ((1aR,3aR,3bS,5aR,6R,8aS,8bS,10R,10aR)-10-Methoxy-3a,5a-dimethyl-hexadecahydro-cyclopenta[a]cyclopropa[2,3]cyclopenta[1,2-f]naphthalen-6-yl)-acetic acid ethyl ester 
• 64595-28-4 (R)-5-[(R)-3-((1aR,3aR,3bS,5aR,6R,8aS,8bS,10R,10aR)-10-Methoxy-3a,5a-dimethyl-hexadecahydro-cyclopenta[a]cyclopropa[2,3]cyclopenta[1,2-f]naphthalen-6-yl)-butyl]-2,2,4,4-tetramethyl-[1,3]dioxolane 
• 474432-41-2 (3β,5Z,7E,24R)-3-[(tert-butyldimethylsilyl)oxy]-9,10-secocholesta-5,7,10(19)-triene-24,25-diol cyclic 24,25-(1-methylethylidene acetal) 
• 474432-39-8 (24R)-de-A,B-24,25-dihydroxycholestan-8-one cyclic 24,25-(1-methylethylidene acetal) 
• 239100-24-4 (8β,24R)-de-A,B-cholesta-8,24,25-triol cyclic 24,25-(1-methylethylidene acetal) 
• 226569-00-2 (1R,3aR,4S,7aR)-1-[(1R,4R)-4,5-dihydroxy-1,5-dimethylhexyl]-7a-methyl-octahydro-1H-inden-4-ol 
• 136463-14-4 C₃₂H₄₀N₂O₅ 

Relevant articles and documents

Chemical Synthesis of Side-Chain-Hydroxylated Vitamin D3 Derivatives and Their Metabolism by CYP27B1

1α,25-Dihydroxyvitamin D3 (abbreviated here as 1,25D3) is a hormonally active form of vitamin D3 (D3), and is produced from D3 by CYP27 A1-mediated hydroxylation at C25, followed by CYP27B1-mediated hydroxylation at C1. Further hydroxylation of 25D3 and 1,25D3 occurs at C23, C24 and C26 to generate corresponding metabolites, except for 1,25R,26D3. Since the capability of CYP27B1 to hydroxylate C1 of side-chain-hydroxylated metabolites other than 23S,25D3 and 24R,25D3 has not been examined, we have here explored the role of CYP27B1 in the C1 hydroxylation of a series of side-chain-hydroxylated D3 derivatives. We found that CYP27B1 hydroxylates the R diastereomers of 24,25D3 and 25,26D3 more effectively than the S diastereomers, but shows almost no activity towards either diastereomer of 23,25D3. This is the first report to show that CYP27B1 metabolizes 25,26D3 to the corresponding 1α-hydroxylated derivative, 1,25,26D3. It will be interesting to examine the physiological relevance of this finding.

A short practical approach to 24R,25-dihydroxyvitamin D3

A synthesis of the vitamin D3 metabolite 24R,25-dihydroxyvitamin D3 (1) by Lythgoe's Wittig-Horner approach is described. The key step of the synthesis is the stereocontrolled introduction of the 24-hydroxyl group by a palladium(0)-induced [3,3]-sigmatropic rearrangement on a 22R-allylic acetate (7).

Stereoselective convergent synthesis of 24,25-dihydroxyvitamin D3 metabolites: a practical approach.

Vitamin D3 active metabolites 24R,25-(OH)2-D3, 24S,25-(OH)2-D3, and 1 alpha, 24R,25-(OH)3-D3 were synthesized by a convergent and stereoselective approach. In the synthetic route, the stereogenic center at C-24 was generated through ultrasonically induced aqueous conjugate addition of iodide 6 to Seebach's dioxolanone 5, and the vitamin D triene system was constructed using the Lythgoe approach. The synthesis, which is both short (seven steps from iodide 6) and efficient (32-40% overall yield), allows the preparation of large quantities of the metabolites and provides a novel example of a highly stereoselective reaction promoted by the zinc-copper couple in aqueous media.

Characterization of new conjugated metabolites in bile of rats administered 24,25-dihydroxyvitamin D3 and 25-hydroxyvitamin D3

The characterization of new conjugated vitamin D metabolites in rat bile was performed using HPLC, liquid chromatography/tandem mass spectrometry combined derivatization, and GC-MS. After the administration of 24,25- dihydroxyvitamin D3 to rats

SYNTHESIS OF (24R)-24,25-DIHYDROXYVITAMIN D3

Two versions of the stereoselective synthesis of (24R)-24,25-dihydroxyvitamin D3 were realized.Vitamin D2 and ergosterol were used as starting materials.Methods are proposed for the production of the following key compounds: 6-Methoxy-23,24-bisnor-9,10-seco-3,5-cyclochola-7,10(19)-dien-22-yl phenyl sulfone; 3β-hydroxy-23,24-bisnorchola-5,7-dien-22-yl phenyl sulfone; (2R)-3-methylbutane-1,2,3-triol 1-p-toluenesulfonate.

Process for the stereospecific preparation of 24(R),25- and 24(S),25-dihydroxycholecalciferol and novel intermediates used therefor

A novel process for the stereospecific preparation of a 24(R),25- and 24(S),25-dihydroxycholecalciferol. Also provided are novel intermediates used in the above process, being 22-p-toluenesulfonyl derivatives of 23,24,25,26,27-pentanorcholecalciferol and

USE OF MALIC ACID AS A CHIRAL SYNTHON: 24,25-DIHYDROXYCHOLECALCIFEROL

A new chiral synthon prepared from malic acid is introduced and utilized in a synthesis of 24,25-dihydroxycholecalciferol.

Stereoselective Introduction of Hydroxy Groups into the Cholesterol Side Chain. Preparation of (24R)- and (24S)-24,25-Dihydroxy- and (25R)- and (25S)-25,26-Dihydroxyvitamin D3 by Asymmetric Synthesis

24,25-Epoxy-26-hydroxy-3β-tetrahydropyranyloxycholest-5-enes (7a) and (8a), prepared by asymmetric epoxidation of the allylic alcohol (4), and 24-hydroxy-3β-tetrahydropyranyloxycholesta-5,25-dienes (11) and (12), synthesized by asymmetric reduction of the enone (6), were stereoselectively converted into 25,26-and 24,25-dihydroxycholesterol derivatives, which could be transformed into 25,26- and 24,25-dihydroxyvitamin D3.The highly stereoselective epoxide cleavage of 26-benzoyloxy-24,25-epoxides (7b), (8b), (25), and (26) was found to proceed with retention at C-24.

24,25-Dihydroxycholestans and process for preparing the same

A 24,25-dihydroxycholestane derivatives of the formula STR1 wherein A is a steroid residue and R is an aryl group and a process for preparation of the same are disclosed. The derivatives are an intermediate for synthesis of 24,25-dihydroxycholecalciferol having useful physicological activity like that of vitamin D3. 24,25-Dihydroxycholecalciferol can be produced in an industrially advantageous method via the intermediate which is easily prepared from commercially available starting compounds.

25-Hydroxy-24-oxocholestane derivatives and preparation thereof

This invention relates to novel 25-hydroxy-24-oxocholestane derivatives and a process for preparing them. The novel 25-hydroxy-24-oxocholestane derivatives of this invention can easily be converted to 24,25-dihydroxycholecalciferol or 1α,24,25-trihydroxyc