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Cas Database

57333-96-7

57333-96-7

Identification

  • Product Name:Tacalcitol

  • CAS Number: 57333-96-7

  • EINECS:

  • Molecular Weight:416.645

  • Molecular Formula: C27H44O3

  • HS Code:

  • Mol File:57333-96-7.mol

Synonyms:1a,24R-Dihydroxyvitamin D3;Bonalfa;Curatoderm;PRI 2191;TV 02;9,10-Secocholesta-5,7,10(19)-triene-1,3,24-triol,(1a,3b,5Z,7E,24R)- (9CI);1a,24(R)-Dihydroxycholecalciferol;

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Safety information and MSDS view more

  • Pictogram(s):N,T+

  • Hazard Codes:N,T+

  • Signal Word:Danger

  • Hazard Statement:H300 Fatal if swallowed

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician. In case of skin contact Wash off with soap and plenty of water. Consult a physician. In case of eye contact Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician. If swallowed Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.

  • Fire-fighting measures: Suitable extinguishing media Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Wear self-contained breathing apparatus for firefighting if necessary.

  • Accidental release measures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Pick up and arrange disposal. Sweep up and shovel. Keep in suitable, closed containers for disposal.

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Store in cool place. Keep container tightly closed in a dry and well-ventilated place.

  • Exposure controls/personal protection:Occupational Exposure limit valuesBiological limit values Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Eye/face protection Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique(without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Respiratory protection Wear dust mask when handling large quantities. Thermal hazards

Supplier and reference price

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  • Manufacture/Brand:Usbiological
  • Product Description:Tacalcitol
  • Packaging:1mg
  • Price:$ 516
  • Delivery:In stock
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  • Manufacture/Brand:TRC
  • Product Description:Tacalcitol
  • Packaging:1mg
  • Price:$ 320
  • Delivery:In stock
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  • Manufacture/Brand:Medical Isotopes, Inc.
  • Product Description:Tacalcitol 99%
  • Packaging:5 mg
  • Price:$ 2200
  • Delivery:In stock
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  • Manufacture/Brand:Labseeker
  • Product Description:Tacalcitol 95
  • Packaging:50mg
  • Price:$ 2462
  • Delivery:In stock
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  • Manufacture/Brand:DC Chemicals
  • Product Description:Tacalcitol >99%
  • Packaging:250 mg
  • Price:$ 2500
  • Delivery:In stock
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  • Manufacture/Brand:DC Chemicals
  • Product Description:Tacalcitol >99%
  • Packaging:1 g
  • Price:$ 4500
  • Delivery:In stock
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  • Manufacture/Brand:CSNpharm
  • Product Description:Tacalcitol
  • Packaging:1mg
  • Price:$ 144
  • Delivery:In stock
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  • Manufacture/Brand:Crysdot
  • Product Description:Tacalcitol 98+%
  • Packaging:10mg
  • Price:$ 669
  • Delivery:In stock
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  • Manufacture/Brand:Crysdot
  • Product Description:Tacalcitol 98+%
  • Packaging:5mg
  • Price:$ 402
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  • Manufacture/Brand:Crysdot
  • Product Description:Tacalcitol 98+%
  • Packaging:50mg
  • Price:$ 2008
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Relevant articles and documentsAll total 7 Articles be found

Process Development of Tacalcitol

Lee, Seung Jong,Moon, Hyung Wook,Lee, Kee-Young,Oh, Chang Young,Kim, U Bin,Shin, Hyunik

, p. 982 - 987 (2021/03/15)

A highly convergent, gram-scale synthesis of vitamin D3 analogue tacalcitol 1 is disclosed, starting from L-valine and Inhoffen-Lythgoe diol. Key features of the synthesis include modified Julia olefination reaction of β-oxybenzothiazol-2-yl sulfone with C/D ring containing aldehyde to access decagrams of fully functionalized C/D ring synthon. The Horner-Wadsworth-Emmons (HWE) reaction between the C/D ring fragment and commercially available phosphonate completes the carbo-skeleton, which is elaborated into tacalcitol 1 in a gram-scale synthesis.

Process for Preparing Tacalcitol and Intermediate Therefor

-

, (2018/12/12)

The present invention relates to a process for preparing tacalcitol and an intermediate body used therefor. According to the preparation method of the present invention, tacalcitol can be effectively and economically prepared without a complex and long preparation process.COPYRIGHT KIPO 2018

Enantiomeric impurity PY2 of tacalcitol and preparation method and application thereof

-

, (2018/05/30)

The invention discloses an enantiomeric impurity PY2 of tacalcitol, i.e., (1 alpha, 3 beta, 5Z, 7E, 24S)-9,10-Secocholesta-5,7,10(19)-triene-1,3,24-triol, and a preparation method thereof, and belongsto the technical field of chemical pharmaceutical. The high-purity relevant impurity PY2 of the tacalcitol, which is disclosed by the invention, can be used as an impurity standard substance in the tacalcitol finished product detection analysis so as to promote accurate positioning and nature determination of the tacalcitol finished product detection analysis on the impurity and benefit reinforcement of control on the impurity, thereby improving quality of a tacalcitol finished product. The method provided by the invention has the advantages that the raw materials are cheap and easy to obtain, the operation is simple, the reproducibility is good in and the HPLC (High Performance Liquid Chromatography) purity is greater than or equal to 99.5%.

Modified Julia olefination and α aminoxylation reactions mediated convergent synthesis of 1α, 24 (R)-dihydroxyvitamin D3 (tacalcitol)

Martínez, Andrea,Santalla, Hugo,Garrido, Fátima,Gómez, Generosa,Fall, Yagamare

, p. 3568 - 3570 (2017/10/06)

A convergent synthesis of tacalcitol has been achieved starting from inexpensive and commercially available isovaleraldehyde and easily available Inhoffen-Lythgoe diol. Key steps include a proline catalyzed α aminoxylation and a Julia-Kocienski olefination.

A he cassie is mellow method for the preparation of

-

, (2016/10/09)

The invention discloses a method for preparing tacalcitol. The method comprises the following steps: with a compound I as a starting raw material, carrying out Wittig reaction, CBS catalytic asymmetric reduction, hydroxy protection, hydrogenation reduction, desilication ether protection and oxidation reaction to prepare a compound VIII, carrying out Wittig Horner reaction on the compound VIII and a known compound IX for coupling, and carrying out dehydroxylation protection to obtain the target compound, namely tacalcitol. With cheap raw materials as the starting point, the method disclosed by the invention is simple, convenient and safe, steps unfavorable to amplification, such as illumination reaction and sodium amalgam reduction reaction, are avoided, and industrial production is facilitated.

Process route upstream and downstream products

Process route

((1R,3S,Z)-5-((E)-2-((1R,7aR)-7a-methyl-1((2R,5R)-6-methyl-5-(triethylsilyloxy)heptan-2-yl)dihydro-1H-inden-4(2H,5H,6H,7H,7aH)-ylidene)ethylidene)-4-methylenecyclohexane-1,3-diyl)bis(oxy)bis(tert-butyldimethylsilane)

((1R,3S,Z)-5-((E)-2-((1R,7aR)-7a-methyl-1((2R,5R)-6-methyl-5-(triethylsilyloxy)heptan-2-yl)dihydro-1H-inden-4(2H,5H,6H,7H,7aH)-ylidene)ethylidene)-4-methylenecyclohexane-1,3-diyl)bis(oxy)bis(tert-butyldimethylsilane)

tacalcitol
57333-96-7

tacalcitol

Conditions
Conditions Yield
With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; Darkness;
98%
With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 40h; Darkness;
98%
(1R,3S)-5-[2-[(1R,3aS,7aR)-1-((1R,4R)-4-Methoxymethoxy-1,5-dimethyl-hexyl)-7a-methyl-octahydro-inden-(4E)-ylidene]-eth-(Z)-ylidene]-4-methylene-cyclohexane-1,3-diol

(1R,3S)-5-[2-[(1R,3aS,7aR)-1-((1R,4R)-4-Methoxymethoxy-1,5-dimethyl-hexyl)-7a-methyl-octahydro-inden-(4E)-ylidene]-eth-(Z)-ylidene]-4-methylene-cyclohexane-1,3-diol

tacalcitol
57333-96-7

tacalcitol

Conditions
Conditions Yield
With hydrogen fluoride; In water; acetonitrile; at 20 ℃; for 24h;
76%
With methanol; AG 50W-X4 resin; at 20 ℃;
33 mg
C<sub>39</sub>H<sub>72</sub>O<sub>3</sub>Si<sub>2</sub>

C39H72O3Si2

tacalcitol
57333-96-7

tacalcitol

Conditions
Conditions Yield
With (1S)-10-camphorsulfonic acid; In methanol; chloroform; at 20 ℃; for 2.5h;
65%
C39H72O3Si2; With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 50 - 55 ℃; for 2h;
With maleic anhydride; In ethyl acetate; at 30 - 35 ℃; for 24h;
300 mg
C<sub>41</sub>H<sub>74</sub>O<sub>4</sub>Si<sub>2</sub>

C41H74O4Si2

tacalcitol
57333-96-7

tacalcitol

Conditions
Conditions Yield
C41H74O4Si2; With potassium carbonate; In methanol; at 20 ℃; for 5h;
With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 2h; Reflux;
75%
C<sub>46</sub>H<sub>76</sub>O<sub>4</sub>Si<sub>2</sub>

C46H76O4Si2

tacalcitol
57333-96-7

tacalcitol

Conditions
Conditions Yield
C46H76O4Si2; With potassium carbonate; In methanol; at 20 ℃; for 5h;
With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 2h; Reflux;
75%
(8S,20S)-de-A,B-20-(hydroxymethyl)pregnan-8-ol
64190-52-9

(8S,20S)-de-A,B-20-(hydroxymethyl)pregnan-8-ol

tacalcitol
57333-96-7

tacalcitol

Conditions
Conditions Yield
Multi-step reaction with 14 steps
1.1: 93 percent / pyridine / 12 h / 0 °C
2.1: 91 percent / dimethylsulfoxide / 2 h / 90 °C
3.1: 98 percent / imidazole / dimethylformamide / 12 h / 80 °C
4.1: lithium diisopropylamide / tetrahydrofuran; hexane / 1 h / -78 - 0 °C
4.2: 91 percent / hexamethylphosphoramide / tetrahydrofuran; hexane / 7 h / -60 - 20 °C
5.1: 94 percent / tert-butanol; potassium; hexamethylphosphoramide / diethyl ether / 13 h / 0 - 20 °C
6.1: 93 percent / N,N-diisopropylethylamine / CH2Cl2 / 0 - 20 °C
7.1: 97 percent / tetrabutylammonium fluoride / tetrahydrofuran / 18 h / Heating
8.1: 96 percent / pyridinium dichromate; pyridinium p-toluenesulfonate / CH2Cl2 / 40 h / 0 °C
9.1: lithium diisopropylamide / hexane; tetrahydrofuran / 2 h / -78 - 20 °C
9.2: 76 percent / tetrahydrofuran; hexane / -78 - 20 °C
10.1: 92 percent / Et3N / bis-triphenylphosphine palladium dichloride / dimethylformamide / 2 h / 70 °C
11.1: 83 percent / hydrogen; quinoline / Lindlar catalyst / hexane / 0.5 h
12.1: 94 percent / 2,2,4-trimethyl-pentane / 4 h / Heating
13.1: tetrabutylammonium fluoride / tetrahydrofuran / 20 h / 20 °C
14.1: 33 mg / AG 50W-X4 resin; methanol / 20 °C
With pyridine; 1H-imidazole; quinoline; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; dipyridinium dichromate; AG 50W-X4 resin; tetrabutyl ammonium fluoride; hydrogen; potassium; pyridinium p-toluenesulfonate; triethylamine; N-ethyl-N,N-diisopropylamine; tert-butyl alcohol; lithium diisopropyl amide; bis-triphenylphosphine-palladium(II) chloride; Lindlar's catalyst; In tetrahydrofuran; 2,2,4-trimethylpentane; diethyl ether; hexane; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; 1.1: Tosylation / 2.1: Substitution / 3.1: silylation / 4.1: Metallation / 4.2: Addition / 5.1: decyanation / 6.1: Etherification / 7.1: desilylation / 8.1: Oxidation / 9.1: Metallation / 9.2: triflation / 10.1: Condensation / 11.1: Hydrogenation / 12.1: Isomerization / 13.1: desilylation / 14.1: methanolysis;
Multi-step reaction with 11 steps
1: 1H-imidazole; dmap / N,N-dimethyl-formamide / 96 h / 20 °C
2: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 20 °C
3: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 12 h / 0 - 20 °C
4: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 12 h / 0 - 20 °C
5: lithium hexamethyldisilazane / tetrahydrofuran / 15 h / -78 - 20 °C
6: tetrabutyl ammonium fluoride / tetrahydrofuran / 17 h / 65 °C
7: hydrogen; palladium 10% on activated carbon / methanol / 15 h
8: dipyridinium dichromate / dichloromethane / 20 °C
9: n-butyllithium / tetrahydrofuran / 18 h / -78 °C
10: tetrabutyl ammonium fluoride / tetrahydrofuran / 20 °C / Darkness
11: hydrogen fluoride / acetonitrile; water / 24 h / 20 °C
With 1H-imidazole; dmap; dipyridinium dichromate; n-butyllithium; di-isopropyl azodicarboxylate; palladium 10% on activated carbon; hydrogen fluoride; tetrabutyl ammonium fluoride; hydrogen; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;
Multi-step reaction with 10 steps
1.1: 1H-imidazole / N,N-dimethyl-formamide / 50 - 55 °C
2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / -5 - 5 °C
3.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; potassium bromide; sodium hypochlorite; sodium hydrogencarbonate / dichloromethane; water / 0.17 h / -5 - 5 °C
4.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -70 - -60 °C
4.2: -70 - 20 °C
5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 55 - 60 °C
6.1: pyridinium chlorochromate / dichloromethane / 20 °C
7.1: palladium 10% on activated carbon; hydrogen / tetrahydrofuran; methanol / 24 h / 2280.15 - 2660.18 Torr
8.1: 1H-imidazole / N,N-dimethyl-formamide / 2 h / 20 °C
9.1: n-butyllithium / tetrahydrofuran / 1 h / -70 - -60 °C
9.2: 1.5 h / -65 - -10 °C
10.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 20 °C / Darkness
With 1H-imidazole; sodium hypochlorite; n-butyllithium; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; palladium 10% on activated carbon; tetrabutyl ammonium fluoride; hydrogen; sodium hexamethyldisilazane; sodium hydrogencarbonate; pyridinium chlorochromate; potassium bromide; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide;
Multi-step reaction with 10 steps
1.1: 1H-imidazole; ammonium chloride / N,N-dimethyl-formamide / 50 - 55 °C / Inert atmosphere
2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 0 °C / Inert atmosphere
3.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene / dichloromethane / 4 h / 20 °C / Inert atmosphere
4.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -70 °C / Inert atmosphere
4.2: -70 - 20 °C / Inert atmosphere
5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 60 °C / Inert atmosphere
6.1: dipyridinium dichromate / dichloromethane / 20 °C
7.1: palladium 10% on activated carbon; hydrogen / tetrahydrofuran; methanol / 24 h / 2280.15 - 2660.18 Torr
8.1: 1H-imidazole / N,N-dimethyl-formamide / 2 h / 20 °C / Inert atmosphere
9.1: n-butyllithium / tetrahydrofuran / 1 h / -65 °C / Inert atmosphere
9.2: 1.5 h / -65 - -10 °C / Inert atmosphere
10.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 40 h / 20 °C / Darkness
With 1H-imidazole; dipyridinium dichromate; n-butyllithium; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; palladium 10% on activated carbon; tetrabutyl ammonium fluoride; hydrogen; sodium hexamethyldisilazane; ammonium chloride; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; 4.1: |Julia Olefin Synthesis / 4.2: |Julia Olefin Synthesis / 9.1: |Horner-Wadsworth-Emmons Olefination / 9.2: |Horner-Wadsworth-Emmons Olefination;
De-A,B-(24R)-24-[(methoxymethyl)oxy]-cholestan-8-one
188949-00-0

De-A,B-(24R)-24-[(methoxymethyl)oxy]-cholestan-8-one

tacalcitol
57333-96-7

tacalcitol

Conditions
Conditions Yield
Multi-step reaction with 6 steps
1.1: lithium diisopropylamide / hexane; tetrahydrofuran / 2 h / -78 - 20 °C
1.2: 76 percent / tetrahydrofuran; hexane / -78 - 20 °C
2.1: 92 percent / Et3N / bis-triphenylphosphine palladium dichloride / dimethylformamide / 2 h / 70 °C
3.1: 83 percent / hydrogen; quinoline / Lindlar catalyst / hexane / 0.5 h
4.1: 94 percent / 2,2,4-trimethyl-pentane / 4 h / Heating
5.1: tetrabutylammonium fluoride / tetrahydrofuran / 20 h / 20 °C
6.1: 33 mg / AG 50W-X4 resin; methanol / 20 °C
With quinoline; methanol; AG 50W-X4 resin; tetrabutyl ammonium fluoride; hydrogen; triethylamine; lithium diisopropyl amide; bis-triphenylphosphine-palladium(II) chloride; Lindlar's catalyst; In tetrahydrofuran; 2,2,4-trimethylpentane; hexane; N,N-dimethyl-formamide; 1.1: Metallation / 1.2: triflation / 2.1: Condensation / 3.1: Hydrogenation / 4.1: Isomerization / 5.1: desilylation / 6.1: methanolysis;
Multi-step reaction with 3 steps
1: n-butyllithium / tetrahydrofuran / 18 h / -78 °C
2: tetrabutyl ammonium fluoride / tetrahydrofuran / 20 °C / Darkness
3: hydrogen fluoride / acetonitrile; water / 24 h / 20 °C
With n-butyllithium; hydrogen fluoride; tetrabutyl ammonium fluoride; In tetrahydrofuran; water; acetonitrile;
De-A,B-(24R)-8β-hydroxy-cholestan-24-ol methoxymethyl ether
188948-99-4

De-A,B-(24R)-8β-hydroxy-cholestan-24-ol methoxymethyl ether

tacalcitol
57333-96-7

tacalcitol

Conditions
Conditions Yield
Multi-step reaction with 7 steps
1.1: 96 percent / pyridinium dichromate; pyridinium p-toluenesulfonate / CH2Cl2 / 40 h / 0 °C
2.1: lithium diisopropylamide / hexane; tetrahydrofuran / 2 h / -78 - 20 °C
2.2: 76 percent / tetrahydrofuran; hexane / -78 - 20 °C
3.1: 92 percent / Et3N / bis-triphenylphosphine palladium dichloride / dimethylformamide / 2 h / 70 °C
4.1: 83 percent / hydrogen; quinoline / Lindlar catalyst / hexane / 0.5 h
5.1: 94 percent / 2,2,4-trimethyl-pentane / 4 h / Heating
6.1: tetrabutylammonium fluoride / tetrahydrofuran / 20 h / 20 °C
7.1: 33 mg / AG 50W-X4 resin; methanol / 20 °C
With quinoline; methanol; dipyridinium dichromate; AG 50W-X4 resin; tetrabutyl ammonium fluoride; hydrogen; pyridinium p-toluenesulfonate; triethylamine; lithium diisopropyl amide; bis-triphenylphosphine-palladium(II) chloride; Lindlar's catalyst; In tetrahydrofuran; 2,2,4-trimethylpentane; hexane; dichloromethane; N,N-dimethyl-formamide; 1.1: Oxidation / 2.1: Metallation / 2.2: triflation / 3.1: Condensation / 4.1: Hydrogenation / 5.1: Isomerization / 6.1: desilylation / 7.1: methanolysis;
Multi-step reaction with 4 steps
1: dipyridinium dichromate / dichloromethane / 20 °C
2: n-butyllithium / tetrahydrofuran / 18 h / -78 °C
3: tetrabutyl ammonium fluoride / tetrahydrofuran / 20 °C / Darkness
4: hydrogen fluoride / acetonitrile; water / 24 h / 20 °C
With dipyridinium dichromate; n-butyllithium; hydrogen fluoride; tetrabutyl ammonium fluoride; In tetrahydrofuran; dichloromethane; water; acetonitrile;
(S)-2-((3R,3aR,7S,7aR)-octahydro-7-hydroxy-3a-methyl-1H-inden-3-yl)propyl 4-methylbenzenesulfonate
66774-80-9,111924-49-3

(S)-2-((3R,3aR,7S,7aR)-octahydro-7-hydroxy-3a-methyl-1H-inden-3-yl)propyl 4-methylbenzenesulfonate

tacalcitol
57333-96-7

tacalcitol

Conditions
Conditions Yield
Multi-step reaction with 13 steps
1.1: 91 percent / dimethylsulfoxide / 2 h / 90 °C
2.1: 98 percent / imidazole / dimethylformamide / 12 h / 80 °C
3.1: lithium diisopropylamide / tetrahydrofuran; hexane / 1 h / -78 - 0 °C
3.2: 91 percent / hexamethylphosphoramide / tetrahydrofuran; hexane / 7 h / -60 - 20 °C
4.1: 94 percent / tert-butanol; potassium; hexamethylphosphoramide / diethyl ether / 13 h / 0 - 20 °C
5.1: 93 percent / N,N-diisopropylethylamine / CH2Cl2 / 0 - 20 °C
6.1: 97 percent / tetrabutylammonium fluoride / tetrahydrofuran / 18 h / Heating
7.1: 96 percent / pyridinium dichromate; pyridinium p-toluenesulfonate / CH2Cl2 / 40 h / 0 °C
8.1: lithium diisopropylamide / hexane; tetrahydrofuran / 2 h / -78 - 20 °C
8.2: 76 percent / tetrahydrofuran; hexane / -78 - 20 °C
9.1: 92 percent / Et3N / bis-triphenylphosphine palladium dichloride / dimethylformamide / 2 h / 70 °C
10.1: 83 percent / hydrogen; quinoline / Lindlar catalyst / hexane / 0.5 h
11.1: 94 percent / 2,2,4-trimethyl-pentane / 4 h / Heating
12.1: tetrabutylammonium fluoride / tetrahydrofuran / 20 h / 20 °C
13.1: 33 mg / AG 50W-X4 resin; methanol / 20 °C
With 1H-imidazole; quinoline; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; dipyridinium dichromate; AG 50W-X4 resin; tetrabutyl ammonium fluoride; hydrogen; potassium; pyridinium p-toluenesulfonate; triethylamine; N-ethyl-N,N-diisopropylamine; tert-butyl alcohol; lithium diisopropyl amide; bis-triphenylphosphine-palladium(II) chloride; Lindlar's catalyst; In tetrahydrofuran; 2,2,4-trimethylpentane; diethyl ether; hexane; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; 1.1: Substitution / 2.1: silylation / 3.1: Metallation / 3.2: Addition / 4.1: decyanation / 5.1: Etherification / 6.1: desilylation / 7.1: Oxidation / 8.1: Metallation / 8.2: triflation / 9.1: Condensation / 10.1: Hydrogenation / 11.1: Isomerization / 12.1: desilylation / 13.1: methanolysis;
<1R-<1β(R*),3aα,4β,7aβ>>-octahydro-4-hydroxy-β,7a-dimethyl-1H-indene-1-propanenitrile
93489-60-2

<1R-<1β(R*),3aα,4β,7aβ>>-octahydro-4-hydroxy-β,7a-dimethyl-1H-indene-1-propanenitrile

tacalcitol
57333-96-7

tacalcitol

Conditions
Conditions Yield
Multi-step reaction with 12 steps
1.1: 98 percent / imidazole / dimethylformamide / 12 h / 80 °C
2.1: lithium diisopropylamide / tetrahydrofuran; hexane / 1 h / -78 - 0 °C
2.2: 91 percent / hexamethylphosphoramide / tetrahydrofuran; hexane / 7 h / -60 - 20 °C
3.1: 94 percent / tert-butanol; potassium; hexamethylphosphoramide / diethyl ether / 13 h / 0 - 20 °C
4.1: 93 percent / N,N-diisopropylethylamine / CH2Cl2 / 0 - 20 °C
5.1: 97 percent / tetrabutylammonium fluoride / tetrahydrofuran / 18 h / Heating
6.1: 96 percent / pyridinium dichromate; pyridinium p-toluenesulfonate / CH2Cl2 / 40 h / 0 °C
7.1: lithium diisopropylamide / hexane; tetrahydrofuran / 2 h / -78 - 20 °C
7.2: 76 percent / tetrahydrofuran; hexane / -78 - 20 °C
8.1: 92 percent / Et3N / bis-triphenylphosphine palladium dichloride / dimethylformamide / 2 h / 70 °C
9.1: 83 percent / hydrogen; quinoline / Lindlar catalyst / hexane / 0.5 h
10.1: 94 percent / 2,2,4-trimethyl-pentane / 4 h / Heating
11.1: tetrabutylammonium fluoride / tetrahydrofuran / 20 h / 20 °C
12.1: 33 mg / AG 50W-X4 resin; methanol / 20 °C
With 1H-imidazole; quinoline; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; dipyridinium dichromate; AG 50W-X4 resin; tetrabutyl ammonium fluoride; hydrogen; potassium; pyridinium p-toluenesulfonate; triethylamine; N-ethyl-N,N-diisopropylamine; tert-butyl alcohol; lithium diisopropyl amide; bis-triphenylphosphine-palladium(II) chloride; Lindlar's catalyst; In tetrahydrofuran; 2,2,4-trimethylpentane; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; 1.1: silylation / 2.1: Metallation / 2.2: Addition / 3.1: decyanation / 4.1: Etherification / 5.1: desilylation / 6.1: Oxidation / 7.1: Metallation / 7.2: triflation / 8.1: Condensation / 9.1: Hydrogenation / 10.1: Isomerization / 11.1: desilylation / 12.1: methanolysis;

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