Welcome to LookChem.com Sign In|Join Free

CAS

  • or

57333-96-7

Post Buying Request

57333-96-7 Suppliers

Recommended suppliersmore

  • Product
  • FOB Price
  • Min.Order
  • Supply Ability
  • Supplier
  • Contact Supplier

57333-96-7 Usage

Description

Tacalcitol, the second vitamin D analog developed as a topical antipsoriatic, was introduced for keratosis, psoriasis, ichthyosis, pityriasis rubra pilaris and palmoplantar pustulosis and keratoderma. It shows improvement in appearance of skin lesions for psoriasis patients without significant side effects. In patients with psoriasis vulgaris, it effectively inhibits keratinocyte growth. Some in vitro studies have shown that tacalcitol inhibits interleukin-1-α-induced granulocyte macrophage colony-stimulating-factor mRNA expression of the human dermal microvascular endothelial cells, which may be involved in mediation of angioproliferation in skin inflammation.

Originator

Teijin (Japan)

Brand name

Bonalfa

Safety Profile

A poison by ingestion, subcutaneous, and intravenous routes. When heated to decomposition it emits acrid smoke and irritating vapors,

Check Digit Verification of cas no

The CAS Registry Mumber 57333-96-7 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 5,7,3,3 and 3 respectively; the second part has 2 digits, 9 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 57333-96:
(7*5)+(6*7)+(5*3)+(4*3)+(3*3)+(2*9)+(1*6)=137
137 % 10 = 7
So 57333-96-7 is a valid CAS Registry Number.
InChI:InChI=1/C27H44O3/c1-17(2)25(29)13-8-18(3)23-11-12-24-20(7-6-14-27(23,24)5)9-10-21-15-22(28)16-26(30)19(21)4/h9-10,17-18,22-26,28-30H,4,6-8,11-16H2,1-3,5H3/b20-9+,21-10-/t18-,22-,23-,24+,25-,26+,27-/m1/s1

57333-96-7 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
  • Price
  • Detail
  • Sigma

  • (SMB00579)  Tacalcitol  ≥99% (HPLC)

  • 57333-96-7

  • SMB00579-1MG

  • 2,541.24CNY

  • Detail

57333-96-7SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 19, 2017

Revision Date: Aug 19, 2017

1.Identification

1.1 GHS Product identifier

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

1.2 Other means of identification

Product number -
Other names Curatoderm

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:57333-96-7 SDS

57333-96-7Synthetic 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
ConditionsYield
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
ConditionsYield
With hydrogen fluoride In water; acetonitrile at 20℃; for 24h;76%
With methanol; AG 50W-X4 resin at 20℃; methanolysis;33 mg
C41H74O4Si2

C41H74O4Si2

tacalcitol
57333-96-7

tacalcitol

Conditions
ConditionsYield
Stage #1: C41H74O4Si2 With potassium carbonate In methanol at 20℃; for 5h;
Stage #2: With tetrabutyl ammonium fluoride In tetrahydrofuran for 2h; Reflux;
75%
C46H76O4Si2

C46H76O4Si2

tacalcitol
57333-96-7

tacalcitol

Conditions
ConditionsYield
Stage #1: C46H76O4Si2 With potassium carbonate In methanol at 20℃; for 5h;
Stage #2: With tetrabutyl ammonium fluoride In tetrahydrofuran for 2h; Reflux;
75%
C39H72O3Si2

C39H72O3Si2

tacalcitol
57333-96-7

tacalcitol

Conditions
ConditionsYield
With (1S)-10-camphorsulfonic acid In methanol; chloroform at 20℃; for 2.5h;65%
Stage #1: C39H72O3Si2 With tetrabutyl ammonium fluoride In tetrahydrofuran at 50 - 55℃; for 2h;
Stage #2: With maleic anhydride In ethyl acetate at 30 - 35℃; for 24h;
300 mg
1α,3β,24(R)-trihydroxycholesta-5,7-diene
57701-47-0

1α,3β,24(R)-trihydroxycholesta-5,7-diene

tacalcitol
57333-96-7

tacalcitol

Conditions
ConditionsYield
In diethyl ether Irradiation;
(S)-2-((3R,3aR,7S,7aR)-octahydro-7-hydroxy-3a-methyl-1H-inden-3-yl)propyl 4-methylbenzenesulfonate
66774-80-9

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

tacalcitol
57333-96-7

tacalcitol

Conditions
ConditionsYield
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
View Scheme
(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
ConditionsYield
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
View Scheme
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
View Scheme
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
View Scheme
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
View Scheme
<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
ConditionsYield
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
View Scheme
De-A,B-(24R)-8β-[(tert-butyldimethylsilyl)oxy]-cholestan-24-ol
145223-31-0

De-A,B-(24R)-8β-[(tert-butyldimethylsilyl)oxy]-cholestan-24-ol

tacalcitol
57333-96-7

tacalcitol

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1.1: 93 percent / N,N-diisopropylethylamine / CH2Cl2 / 0 - 20 °C
2.1: 97 percent / tetrabutylammonium fluoride / tetrahydrofuran / 18 h / Heating
3.1: 96 percent / pyridinium dichromate; pyridinium p-toluenesulfonate / CH2Cl2 / 40 h / 0 °C
4.1: lithium diisopropylamide / hexane; tetrahydrofuran / 2 h / -78 - 20 °C
4.2: 76 percent / tetrahydrofuran; hexane / -78 - 20 °C
5.1: 92 percent / Et3N / bis-triphenylphosphine palladium dichloride / dimethylformamide / 2 h / 70 °C
6.1: 83 percent / hydrogen; quinoline / Lindlar catalyst / hexane / 0.5 h
7.1: 94 percent / 2,2,4-trimethyl-pentane / 4 h / Heating
8.1: tetrabutylammonium fluoride / tetrahydrofuran / 20 h / 20 °C
9.1: 33 mg / AG 50W-X4 resin; methanol / 20 °C
View Scheme
(R)-3-((1R,3aR,4S,7aR)-4-((tert-butyldimethylsilyl)oxy)-7a-methyloctahydro-1H-inden-1-yl)butanenitrile
145223-29-6

(R)-3-((1R,3aR,4S,7aR)-4-((tert-butyldimethylsilyl)oxy)-7a-methyloctahydro-1H-inden-1-yl)butanenitrile

tacalcitol
57333-96-7

tacalcitol

Conditions
ConditionsYield
Multi-step reaction with 11 steps
1.1: lithium diisopropylamide / tetrahydrofuran; hexane / 1 h / -78 - 0 °C
1.2: 91 percent / hexamethylphosphoramide / tetrahydrofuran; hexane / 7 h / -60 - 20 °C
2.1: 94 percent / tert-butanol; potassium; hexamethylphosphoramide / diethyl ether / 13 h / 0 - 20 °C
3.1: 93 percent / N,N-diisopropylethylamine / CH2Cl2 / 0 - 20 °C
4.1: 97 percent / tetrabutylammonium fluoride / tetrahydrofuran / 18 h / Heating
5.1: 96 percent / pyridinium dichromate; pyridinium p-toluenesulfonate / CH2Cl2 / 40 h / 0 °C
6.1: lithium diisopropylamide / hexane; tetrahydrofuran / 2 h / -78 - 20 °C
6.2: 76 percent / tetrahydrofuran; hexane / -78 - 20 °C
7.1: 92 percent / Et3N / bis-triphenylphosphine palladium dichloride / dimethylformamide / 2 h / 70 °C
8.1: 83 percent / hydrogen; quinoline / Lindlar catalyst / hexane / 0.5 h
9.1: 94 percent / 2,2,4-trimethyl-pentane / 4 h / Heating
10.1: tetrabutylammonium fluoride / tetrahydrofuran / 20 h / 20 °C
11.1: 33 mg / AG 50W-X4 resin; methanol / 20 °C
View Scheme
De-A,B-(24R,22ξ)-8β-[(tert-butyldimethylsilyl)oxy]-24-hydroxy-cholestane-22-carbonitrile
145223-30-9

De-A,B-(24R,22ξ)-8β-[(tert-butyldimethylsilyl)oxy]-24-hydroxy-cholestane-22-carbonitrile

tacalcitol
57333-96-7

tacalcitol

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1.1: 94 percent / tert-butanol; potassium; hexamethylphosphoramide / diethyl ether / 13 h / 0 - 20 °C
2.1: 93 percent / N,N-diisopropylethylamine / CH2Cl2 / 0 - 20 °C
3.1: 97 percent / tetrabutylammonium fluoride / tetrahydrofuran / 18 h / Heating
4.1: 96 percent / pyridinium dichromate; pyridinium p-toluenesulfonate / CH2Cl2 / 40 h / 0 °C
5.1: lithium diisopropylamide / hexane; tetrahydrofuran / 2 h / -78 - 20 °C
5.2: 76 percent / tetrahydrofuran; hexane / -78 - 20 °C
6.1: 92 percent / Et3N / bis-triphenylphosphine palladium dichloride / dimethylformamide / 2 h / 70 °C
7.1: 83 percent / hydrogen; quinoline / Lindlar catalyst / hexane / 0.5 h
8.1: 94 percent / 2,2,4-trimethyl-pentane / 4 h / Heating
9.1: tetrabutylammonium fluoride / tetrahydrofuran / 20 h / 20 °C
10.1: 33 mg / AG 50W-X4 resin; methanol / 20 °C
View Scheme
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
ConditionsYield
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
View Scheme
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
View Scheme
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
ConditionsYield
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
View Scheme
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
View Scheme
De-A,B-(24R)-24-[(methoxymethyl)oxy]-cholest-8-en-8-yl trifluoromethanesulfonate
188948-96-1

De-A,B-(24R)-24-[(methoxymethyl)oxy]-cholest-8-en-8-yl trifluoromethanesulfonate

tacalcitol
57333-96-7

tacalcitol

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 92 percent / Et3N / bis-triphenylphosphine palladium dichloride / dimethylformamide / 2 h / 70 °C
2: 83 percent / hydrogen; quinoline / Lindlar catalyst / hexane / 0.5 h
3: 94 percent / 2,2,4-trimethyl-pentane / 4 h / Heating
4: tetrabutylammonium fluoride / tetrahydrofuran / 20 h / 20 °C
5: 33 mg / AG 50W-X4 resin; methanol / 20 °C
View Scheme
De-A,B-(24R)-8β-[(tert-butyldimethylsilyl)oxy]-cholestan-24-ol methoxymethyl ether
188948-98-3

De-A,B-(24R)-8β-[(tert-butyldimethylsilyl)oxy]-cholestan-24-ol methoxymethyl ether

tacalcitol
57333-96-7

tacalcitol

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1.1: 97 percent / tetrabutylammonium fluoride / tetrahydrofuran / 18 h / Heating
2.1: 96 percent / pyridinium dichromate; pyridinium p-toluenesulfonate / CH2Cl2 / 40 h / 0 °C
3.1: lithium diisopropylamide / hexane; tetrahydrofuran / 2 h / -78 - 20 °C
3.2: 76 percent / tetrahydrofuran; hexane / -78 - 20 °C
4.1: 92 percent / Et3N / bis-triphenylphosphine palladium dichloride / dimethylformamide / 2 h / 70 °C
5.1: 83 percent / hydrogen; quinoline / Lindlar catalyst / hexane / 0.5 h
6.1: 94 percent / 2,2,4-trimethyl-pentane / 4 h / Heating
7.1: tetrabutylammonium fluoride / tetrahydrofuran / 20 h / 20 °C
8.1: 33 mg / AG 50W-X4 resin; methanol / 20 °C
View Scheme
(24R)-1α-[(tert-butyldimethylsilyl)oxy]-6,7-didehydro-24-[(methoxymethyl)oxy]-previtamin D3 tert-butyldimethylsilyl ether
188948-95-0

(24R)-1α-[(tert-butyldimethylsilyl)oxy]-6,7-didehydro-24-[(methoxymethyl)oxy]-previtamin D3 tert-butyldimethylsilyl ether

tacalcitol
57333-96-7

tacalcitol

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 83 percent / hydrogen; quinoline / Lindlar catalyst / hexane / 0.5 h
2: 94 percent / 2,2,4-trimethyl-pentane / 4 h / Heating
3: tetrabutylammonium fluoride / tetrahydrofuran / 20 h / 20 °C
4: 33 mg / AG 50W-X4 resin; methanol / 20 °C
View Scheme
1α-[(tert-butyldimethylsilyl)oxy]-24R-[(methoxymethyl)oxy]-previtamin D3 tert-butyldimethylsilyl ether
188949-01-1

1α-[(tert-butyldimethylsilyl)oxy]-24R-[(methoxymethyl)oxy]-previtamin D3 tert-butyldimethylsilyl ether

tacalcitol
57333-96-7

tacalcitol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 94 percent / 2,2,4-trimethyl-pentane / 4 h / Heating
2: tetrabutylammonium fluoride / tetrahydrofuran / 20 h / 20 °C
3: 33 mg / AG 50W-X4 resin; methanol / 20 °C
View Scheme
1α-[(tert-butyldimethylsilyl)oxy]-24R-[(methoxymethyl)oxy]-vitamin D3 tert-butyldimethylsilyl ether
188949-02-2

1α-[(tert-butyldimethylsilyl)oxy]-24R-[(methoxymethyl)oxy]-vitamin D3 tert-butyldimethylsilyl ether

tacalcitol
57333-96-7

tacalcitol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: tetrabutylammonium fluoride / tetrahydrofuran / 20 h / 20 °C
2: 33 mg / AG 50W-X4 resin; methanol / 20 °C
View Scheme
Multi-step reaction with 2 steps
1: tetrabutyl ammonium fluoride / tetrahydrofuran / 20 °C / Darkness
2: hydrogen fluoride / acetonitrile; water / 24 h / 20 °C
View Scheme
1α, 3β, 24-trihydroxycholest-5-ene
59780-19-7

1α, 3β, 24-trihydroxycholest-5-ene

tacalcitol
57333-96-7

tacalcitol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: Py
3: diethyl ether / Irradiation
View Scheme
1α, 2α-epoxy-24-keto-cholesta-4,6-dien-3-one
57701-42-5

1α, 2α-epoxy-24-keto-cholesta-4,6-dien-3-one

tacalcitol
57333-96-7

tacalcitol

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: Li, NH4Cl, liq. NH3
2: Py
4: diethyl ether / Irradiation
View Scheme
1α-Hydroxy-3β,24(R)-dibenzoyloxy-cholest-5-ene
57333-97-8

1α-Hydroxy-3β,24(R)-dibenzoyloxy-cholest-5-ene

tacalcitol
57333-96-7

tacalcitol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
2: diethyl ether / Irradiation
View Scheme
C24H46O2Si

C24H46O2Si

tacalcitol
57333-96-7

tacalcitol

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: dichloromethane / 4 h / 0 - 20 °C / Inert atmosphere
2.1: palladium on activated charcoal; hydrogen / methanol / 760.05 Torr
3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 10 h / Reflux
4.1: pyridinium dichromate; aluminum oxide / dichloromethane / 20 h / 20 °C
5.1: n-butyllithium / tetrahydrofuran / 0.5 h / -60 °C / Inert atmosphere
5.2: 2 h / 20 °C
6.1: potassium carbonate / methanol / 5 h / 20 °C
6.2: 2 h / Reflux
View Scheme
C34H50O2Si

C34H50O2Si

tacalcitol
57333-96-7

tacalcitol

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: pyridine / dichloromethane / 5 h / 0 - 20 °C / Inert atmosphere
2.1: palladium on activated charcoal; hydrogen / methanol / 760.05 Torr
3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 10 h / Reflux
4.1: pyridinium dichromate / dichloromethane / 20 h / 20 °C / Inert atmosphere
5.1: n-butyllithium / tetrahydrofuran / 0.5 h / -60 °C / Inert atmosphere
5.2: 2 h / 20 °C
6.1: potassium carbonate / methanol / 5 h / 20 °C
6.2: 2 h / Reflux
View Scheme
C26H48O3Si

C26H48O3Si

tacalcitol
57333-96-7

tacalcitol

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: palladium on activated charcoal; hydrogen / methanol / 760.05 Torr
2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 10 h / Reflux
3.1: pyridinium dichromate; aluminum oxide / dichloromethane / 20 h / 20 °C
4.1: n-butyllithium / tetrahydrofuran / 0.5 h / -60 °C / Inert atmosphere
4.2: 2 h / 20 °C
5.1: potassium carbonate / methanol / 5 h / 20 °C
5.2: 2 h / Reflux
View Scheme
C41H54O3Si

C41H54O3Si

tacalcitol
57333-96-7

tacalcitol

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: palladium on activated charcoal; hydrogen / methanol / 760.05 Torr
2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 10 h / Reflux
3.1: pyridinium dichromate / dichloromethane / 20 h / 20 °C / Inert atmosphere
4.1: n-butyllithium / tetrahydrofuran / 0.5 h / -60 °C / Inert atmosphere
4.2: 2 h / 20 °C
5.1: potassium carbonate / methanol / 5 h / 20 °C
5.2: 2 h / Reflux
View Scheme
C26H50O3Si

C26H50O3Si

tacalcitol
57333-96-7

tacalcitol

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 10 h / Reflux
2.1: pyridinium dichromate; aluminum oxide / dichloromethane / 20 h / 20 °C
3.1: n-butyllithium / tetrahydrofuran / 0.5 h / -60 °C / Inert atmosphere
3.2: 2 h / 20 °C
4.1: potassium carbonate / methanol / 5 h / 20 °C
4.2: 2 h / Reflux
View Scheme
C41H56O3Si

C41H56O3Si

tacalcitol
57333-96-7

tacalcitol

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 10 h / Reflux
2.1: pyridinium dichromate / dichloromethane / 20 h / 20 °C / Inert atmosphere
3.1: n-butyllithium / tetrahydrofuran / 0.5 h / -60 °C / Inert atmosphere
3.2: 2 h / 20 °C
4.1: potassium carbonate / methanol / 5 h / 20 °C
4.2: 2 h / Reflux
View Scheme
C20H36O3

C20H36O3

tacalcitol
57333-96-7

tacalcitol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: pyridinium dichromate; aluminum oxide / dichloromethane / 20 h / 20 °C
2.1: n-butyllithium / tetrahydrofuran / 0.5 h / -60 °C / Inert atmosphere
2.2: 2 h / 20 °C
3.1: potassium carbonate / methanol / 5 h / 20 °C
3.2: 2 h / Reflux
View Scheme
C25H38O3

C25H38O3

tacalcitol
57333-96-7

tacalcitol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: pyridinium dichromate / dichloromethane / 20 h / 20 °C / Inert atmosphere
2.1: n-butyllithium / tetrahydrofuran / 0.5 h / -60 °C / Inert atmosphere
2.2: 2 h / 20 °C
3.1: potassium carbonate / methanol / 5 h / 20 °C
3.2: 2 h / Reflux
View Scheme
tacalcitol
57333-96-7

tacalcitol

1α,24(R)-dihydroxy-6,19-dihydro-6,19-epidioxyvitamin D3

1α,24(R)-dihydroxy-6,19-dihydro-6,19-epidioxyvitamin D3

Conditions
ConditionsYield
With oxygen; rose bengal In ethanol for 1h; Irradiation; Yield given;

57333-96-7Downstream Products

57333-96-7Relevant articles and documents

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.

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%.

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.

Post a RFQ

Enter 15 to 2000 letters.Word count: 0 letters

Attach files(File Format: Jpeg, Jpg, Gif, Png, PDF, PPT, Zip, Rar,Word or Excel Maximum File Size: 3MB)

1

What can I do for you?
Get Best Price

Get Best Price for 57333-96-7