2-(3-hydroxypropoxy)-1,25-dihydroxyvitamin D3

ChemicalBook > CAS DataBase List > 2-(3-hydroxypropoxy)-1,25-dihydroxyvitamin D3

2-(3-hydroxypropoxy)-1,25-dihydroxyvitamin D3

Product Name: 2-(3-hydroxypropoxy)-1,25-dihydroxyvitamin D3
CAS No.: 104121-92-8
Chemical Name: 2-(3-hydroxypropoxy)-1,25-dihydroxyvitamin D3
Synonyms: ED-71;Idecalcitol;Eldecalcitol;El calciditol;Eldecalcitol CRS;Aidit, calcitriol;Eldecalcitol(ED-71);2-(3-hydroxypropoxy)-1,25-dihydroxyvitamin D3;1alpha,25-dihydroxy-2beta-(3-hydroxypropoxy)vitamin D3;104121-92-8 2-(3-hydroxypropoxy)-1,25-dihydroxyvitamin D3
CBNumber: CB71319007
Molecular Formula: C30H50O5
Formula Weight: 490.71
MOL File: 104121-92-8.mol

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2-(3-hydroxypropoxy)-1,25-dihydroxyvitamin D3 Property

Melting point:: 126-128℃
Boiling point:: 655.7±55.0 °C(Predicted)
Density: 1.10
storage temp.: Store at -20°C
solubility: Soluble in DMSO
form: Powder
pka: 13.80±0.60(Predicted)
InChIKey: FZEXGDDBXLBRTD-AYIMTCTASA-N
SMILES: [C@@H]1(O)C/C(=C/C=C2\CCC[C@@]3(C)[C@@]\2([H])CC[C@@H]3[C@H](C)CCCC(O)(C)C)/C(=C)[C@@H](O)[C@@H]1OCCCO

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Hazard and Precautionary Statements (GHS)

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N-Bromosuccinimide Price

TRC

Product number: E555540
Product name: Eldecalcitol
Packaging: 20mg
Price: $34125
Updated: 2021/12/16

Biorbyt Ltd

Product number: orb612008
Product name: Eldecalcitol
Purity: >99%
Packaging: 100mg
Price: $8175.3
Updated: 2021/12/16

American Custom Chemicals Corporation

Product number: VIT0000083
Product name: ELDECALCITOL
Purity: 95.00%
Packaging: 5MG
Price: $497.66
Updated: 2021/12/16

Medical Isotopes, Inc.

Product number: 17940
Product name: Eldecalcitol
Packaging: 1mg
Price: $1190
Updated: 2021/12/16

ChemScene

Product number: CS-0363
Product name: Eldecalcitol
Purity: 99.01%
Packaging: 1mg
Price: $1850
Updated: 2021/12/16

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2-(3-hydroxypropoxy)-1,25-dihydroxyvitamin D3 Chemical Properties,Usage,Production

Description

Eldecalcitol (Edirol) was approved in January 2011 by the Japanese Ministry of Health, Labor, and Welfare for the treatment of osteoporosis. Because of vitamin D’s central role in the bone health, vitamin D and analogs of vitamin D have been used to treat patients diagnosed with osteoporosis. Eldecalcitol is an analog of the active form of vitamin D, calcitriol, in which the lower cyclohexane ring contains a hydroxypropyl group. The synthesis of eldecalcitol involves the assembly of two units, a fully protected (3S,4S,5R)-oct-1-en-7-yne-3,4,5-triol and a fused bicyclic system, (R)-6- ((1R,3aR,7aR,E)-4-(bromomethylene)-7a-methyloctahydro-1H-inden-1- yl)-2-methylheptan-2-ol, through a Diels-Alder reaction to give fully protected eldecalcitol. The hydroxyl groups are then deprotected to give the parent molecule. Eldecalcitol binds to the vitaminDreceptor 2.7-fold more potently than calcitriol, while only weakly inhibiting serum parathyroid hormone.

Originator

Chugai Pharmaceutical/Roche (Japan)

Uses

Eldecalcitol is a derivative of vitamin D3 (V676045) which is the vitamin that mediates intestinal calcium absorbtion, bone calcium metabolism and probably, muscle activity.

Definition

ChEBI: A hydroxycalciol that is calcitriol with a 3-hydroxypropoxy group at position 2.

brand name

Edirol

Clinical Use

Eldecalcitol is a vitamin D3 analog approved in Japan for the treatment of osteoporosis. Itwasdiscoveredby Chugai and co-developed with Taisho. Eldecalcitol, a hormonally active calcitrol analog, regulates calcium and bone metabolism. The drug was approved on the basis of results from randomized, double-blinded, parallelgroup, phase III studies taking place over three years that showed eldecalcitol to significantly lower incidence of new vertebral fractures compared to those receiving the comparator drug alfacalcidol. Discovery and SAR studies of vitamin D3 analogs leading to the identification of eldecalcitol have been reported. In addition, multiple syntheses, including parallel approaches, have been reported in publications and patents.

Synthesis

The biomimetic vitamin D3 analog synthesis that was recently disclosed, based on an earlier reported route for the commercial synthesis of alfacalcidol, will be discussed here.
An Oppenauer oxidation converted commercially available cholesterol 141 to enone 142 in 80% yield. A second oxidation event with DDQ provided dienone 143 in 75% yield. Treatment of 143 with sodium ethoxide in ethanol triggered migration of the enone double bond into the B-ring, giving olefin 144 in 53% yield. Stereospecific reduction of ketone 144 with sodium borohydride gave alcohol 145 in 53% yield, which was then immediately protected as the corresponding acetate with acetic anhydride to furnish 146. Next, further dehydrogenation of the B-ring was accomplished using radical bromination of the olefin within 146 through the use of NBS and catalytic AIBN, followed by elimination with collidine. A subsequent saponification step ultimately gave rise to the key diene 147. Next, in order to selectively epoxidize the A-ring olefin, a unique ??protection?ˉ strategy was employed using phenyl- 1,2,4-triazole-3,5-dione (PTAD). Diels¨CAlder reaction between diene 147 and PTAD produced cycloadduct 148 in 80% overall yield from acetate 146. Protection of the alcohol as the corresponding TBS ether preceeded a regio- and stereospecific epoxidation with m-CPBA to afford 1,2a-epoxide 150 in 78% yield. Diels¨CAlder adduct 150 was then subjected to thermal conditions to affect a retro-[ 4+2] reaction to give diene 151. Fluoride-mediated removal of the TBS group prepared 3b-alcohol 152 in 95% yield. Subsequent ring-opening reaction with 1,3-propane diol in the presence of potassium t-butoxide, provided 3-hydroxy propoxy ether 153 in 29% yield. Microbial oxidation of intermediate 153 was accomplished using an Amycolata autotrophica ATCC 33796 culture to obtain eldecalcitol derivative 154 in 64% yield. Subjection of 154 to 400 watt light followed by thermolysis provided eldecalcitol (XII) in 29% yield.

target

osteoporosis

2-(3-hydroxypropoxy)-1,25-dihydroxyvitamin D3 Preparation Products And Raw materials

Raw materials

Preparation Products

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View Lastest Price from 2-(3-hydroxypropoxy)-1,25-dihydroxyvitamin D3 manufacturers

ShenZhen H&D Pharmaceutical Technology Co., LTD

Product: Eldecalcitol 104121-92-8
Price: US $0.00-0.00/mg
Min. Order: 10mg
Purity: 0.98
Supply Ability: 10g
Release date: 2024-04-24

Hangzhou ICH Biofarm Co., Ltd

Product: Eldecalcitol 104121-92-8
Price: US $0.00-0.00/kg
Min. Order: 1kg
Purity: 98%
Supply Ability: 200
Release date: 2023-07-05

Shaanxi Dideu Medichem Co. Ltd

Product: Eldecalcitol 104121-92-8
Price: US $12.00/KG
Min. Order: 1KG
Purity: 99%
Supply Ability: 100 ton
Release date: 2020-11-21

104121-92-8, 2-(3-hydroxypropoxy)-1,25-dihydroxyvitamin D3Related Search:

2β-trans-eldecalcitol (4S,5R)-2,2-DIMETHYL-4-((R)-OXIRAN-2-YL)-5-VINYL-1,3-DIOXOLANE [(1R,3aR,4S,7aR)-1-[(2S)-1-iodopropan-2-yl]-7a-methyl-1,2,3,3a,4,5,6,7-octahydroinden-4-yl]oxy-tert-butyl-dimethylsilane 933779-95-4 1H-Indene-1-pentanol, 4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]octahydro-α,α,ε,7a-tetramethyl-, (εS,1R,3aR,4S,7aR)- (Z)-[2-{(3R,4R,5R)-3,5-bis(tert-butyldimethylsilanyloxy)-2-methylene-4-(3-(tert-butyldiphenylsilanyloxy)propoxy)cyclohexylidene}ethyl]diphenylphosphine oxide Adicarbitol intermediate 2 215257-72-0 Paricalcitol 1-(2-Hydroxy-1-methyl-ethyl)-7a-methyl-octahydro-inden-4-ol Eldecalcitol A-TBDPS (1R,7AR)-1-((S)-1-HYDROXYPROPAN-2-YL)-7A-METHYLHEXAHYDRO-1H-INDEN-4(2H)-ONE (1R,3aR,7aR)-7a-Methyl-1-((R)-6-Methylheptan-2-yl)hexahydro-1H-inden-4(2H)-one R=TMS 4H-Inden-4-one, 1-[1,5-dimethyl-5-[(triethylsilyl)oxy]hexyl]octahydro-7a-methyl-, [1R-[1α(R*),3aβ,7aα]]- Phosphine oxide, [(2Z)-2-[(3R,4R,5R)-3,5-bis[[(1,1-diMethylethyl)diMethylsilyl]oxy]-4-[3-[[(1,1-diMethylethyl)diMethylsilyl]oxy]propoxy]-2-Methylenecyclohexylidene]ethyl]diphenyl- (1R,3aR,7aR)-1-((R)-6-hydroxy-6-Methylheptan-2-yl)-7a-Methylhexahydro-1H-inden-4(2H)-one Technology transfer of edetolic alcohol and soft capsule

2-(3-hydroxypropoxy)-1,25-dihydroxyvitamin D3

Eldecalcitol

ED-71

(1R,Z)-5-((E)-2-((1R,7aR)-1-((R)-6-hydroxy-6-methylheptan-2-yl)-7a-methylhexahydro-1H-inden-4(2H)-ylidene)ethylidene)-2-(3-hydroxypropoxy)-4-methylenecyclohexane-1,3-diol

1alpha,25-dihydroxy-2beta-(3-hydroxypropoxy)vitamin D3

Eldecalcitol(ED-71)

2.beta.-(3-Hydroxypropoxy)-1.alpha.,25-dihydroxyvitaMin D3

(1S,2S,3S,5Z)-5-[(2E)-2-[(1R,3aS,7aR)-1-[(2R)-6-hydroxy-6-methylheptan-2-yl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-2-(3-hydroxypropoxy)-4-methylidenecyclohexane-1,3-diol

El calciditol

Eldecalcitol {2-(3-hydroxypropoxy)-1,25-dihydroxyvitamin D3}

1,3-Cyclohexanediol, 2-(3-hydroxypropoxy)-4-methylene-5-[(2E)-2-[(1R,3aS,7aR)-octahydro-1-[(1R)-5-hydroxy-1,5-dimethylhexyl]-7a-methyl-4H-inden-4-ylidene]ethylidene]-, (1R,2R,3R,5Z)-

(1R,2R,3R,5Z)-5-[(2E)-2-[(1R,3aS,7aR)-1-[(2R)-6-hydroxy-6-methylheptan-2-yl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-2-(3-hydroxypropoxy)-4-methylidenecyclohexane-1,3-diol

104121-92-8 2-(3-hydroxypropoxy)-1,25-dihydroxyvitamin D3

(1R,2R,3R,Z)-5-((E)-2-((1R,3aS,7aR)-1-((R)-6-Hydroxy-6-methylheptan-2-yl)-7a-methylhexahydro-1H-inden-4(2H)-ylidene)ethylidene)-2-(3-hydroxypropoxy)-4-methylenecyclohexane-1,3-diol

Eldecalcitol CRS

Aidit, calcitriol

Idecalcitol

104121-92-8

04121-92-8