Product Name

  • Name

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

  • EINECS 686-849-3
  • CAS No. 104121-92-8
  • Article Data8
  • CAS DataBase
  • Density 1.105 g/cm3
  • Solubility
  • Melting Point 126-128 °C
  • Formula C30H50O5
  • Boiling Point 655.656 °C at 760 mmHg
  • Molecular Weight 490.724
  • Flash Point 350.328 °C
  • Transport Information
  • Appearance
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 104121-92-8 (2-(3-hydroxypropoxy)-1,25-dihydroxyvitamin D3)
  • Hazard Symbols
  • Synonyms ED 71;2-(3-Hydroxypropoxy)-1,25-dihydroxyvitamin D3;2-(3-Hydroxypropoxy)calcitriol;9,10-Secocholesta-5,7,10(19)-triene-1,3,25-triol, 2-(3-hydroxypropoxy)-, (1alpha,2beta,3beta,5Z,7E)-;
  • PSA 90.15000
  • LogP 5.08220

Synthetic route

(1β,2α,3α,5Z,7E)-1,3-bis[(1,1-dimethylethyl)dimethylsilyloxy]-2-[3-[(1,1-dimethylethyl)dimethylsilyloxy]propoxy]-25-trimethylsilyloxy-9,10-secocholesta-5,7,10(19)-triene
342645-84-5

(1β,2α,3α,5Z,7E)-1,3-bis[(1,1-dimethylethyl)dimethylsilyloxy]-2-[3-[(1,1-dimethylethyl)dimethylsilyloxy]propoxy]-25-trimethylsilyloxy-9,10-secocholesta-5,7,10(19)-triene

Eldecalcitol
104121-92-8

Eldecalcitol

Conditions
ConditionsYield
With pyridine; hydrogen fluoride In tetrahydrofuran at 20℃;96%
C54H106O5Si4

C54H106O5Si4

Eldecalcitol
104121-92-8

Eldecalcitol

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride In tetrahydrofuran at 25℃;89%
((1R,2R,3R,Z)-2-(3-(tert-butyldiphenylsilyloxy)propoxy)-5-((E)-2-((1R,3aS,7aR)-7a-methyl-1-((R)-6-methyl-6-(trimethylsilyloxy)heptan-2-yl)dihydro-1H-indene-4(2H,5H,6H,7H,7aH)-ylidene)ethylidene)-4-methylene cyclohexane-1,3-diyl)bis(oxy)bis(tert-butyldimethylsilane)

((1R,2R,3R,Z)-2-(3-(tert-butyldiphenylsilyloxy)propoxy)-5-((E)-2-((1R,3aS,7aR)-7a-methyl-1-((R)-6-methyl-6-(trimethylsilyloxy)heptan-2-yl)dihydro-1H-indene-4(2H,5H,6H,7H,7aH)-ylidene)ethylidene)-4-methylene cyclohexane-1,3-diyl)bis(oxy)bis(tert-butyldimethylsilane)

Eldecalcitol
104121-92-8

Eldecalcitol

Conditions
ConditionsYield
With toluene-4-sulfonic acid In methanol; dichloromethane at 20℃; for 5h; Inert atmosphere;80%
C38H66O9

C38H66O9

Eldecalcitol
104121-92-8

Eldecalcitol

Conditions
ConditionsYield
With methanol at 20℃; for 66h; Inert atmosphere; stereoselective reaction;68%
(R)-6-{(1R,3aS,7aR)-4-[2-[(3R,4R,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-4-[3-(tert-butyl-dimethyl-silanyloxy)-propoxy]-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-2-methyl-heptan-2-ol

(R)-6-{(1R,3aS,7aR)-4-[2-[(3R,4R,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-4-[3-(tert-butyl-dimethyl-silanyloxy)-propoxy]-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-2-methyl-heptan-2-ol

Eldecalcitol
104121-92-8

Eldecalcitol

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃; for 96h;61%
(5Z,7E)-(1R,2R,3R)-1,3-bis(tert-butyldimethylsilyloxy)-2-(3-tert-butyldimethylsilyloxypropoxy)-25-triethylsilyloxy-9,10-secocholesta-5,7,10(19)-triene
933779-95-4

(5Z,7E)-(1R,2R,3R)-1,3-bis(tert-butyldimethylsilyloxy)-2-(3-tert-butyldimethylsilyloxypropoxy)-25-triethylsilyloxy-9,10-secocholesta-5,7,10(19)-triene

Eldecalcitol
104121-92-8

Eldecalcitol

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride In tetrahydrofuran; toluene at 105℃; for 2h;60%
(5R,6R)-6-((R)-1-(methoxymethoxy)allyl)-5-(prop-2-yn-1-yl)-2,4,7,11,13-pentaoxatetradecane

(5R,6R)-6-((R)-1-(methoxymethoxy)allyl)-5-(prop-2-yn-1-yl)-2,4,7,11,13-pentaoxatetradecane

C21H37BrO2

C21H37BrO2

Eldecalcitol
104121-92-8

Eldecalcitol

Conditions
ConditionsYield
Stage #1: (5R,6R)-6-((R)-1-(methoxymethoxy)allyl)-5-(prop-2-yn-1-yl)-2,4,7,11,13-pentaoxatetradecane; C21H37BrO2 With tetrakis(triphenylphosphine) palladium(0); triethylamine In toluene at 110℃; for 2h;
Stage #2: With camphor-10-sulfonic acid In methanol at 20℃; for 72h;		36%
25-[(triethylsilyl)oxy]de-A,B-cholestan-8-one
144848-24-8

25-[(triethylsilyl)oxy]de-A,B-cholestan-8-one

[3R-(1Z,3β,4α,5α)]-[2-[3,5-bis[(1,1-dimethylethyl)dimethylsilyloxy]-4-[3-[(1,1-dimethylethyl)dimethylsilyloxy]propoxy]-2-methylenecyclohexylidene]ethyl]diphenylphosphine oxide
200636-54-0

[3R-(1Z,3β,4α,5α)]-[2-[3,5-bis[(1,1-dimethylethyl)dimethylsilyloxy]-4-[3-[(1,1-dimethylethyl)dimethylsilyloxy]propoxy]-2-methylenecyclohexylidene]ethyl]diphenylphosphine oxide

Eldecalcitol
104121-92-8

Eldecalcitol

Conditions
ConditionsYield
Multistep reaction;
methyl 4,6-O-benzylidene-3-O-(3-hydroxypropyl)-α-D-altropyranoside
299410-93-8

methyl 4,6-O-benzylidene-3-O-(3-hydroxypropyl)-α-D-altropyranoside

Eldecalcitol
104121-92-8

Eldecalcitol

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1.1: 2.1 g / Et3N; DMAP / CH2Cl2 / 3 h / 20 °C
2.1: 91 percent / BaCO3; NBS / CCl4 / Heating
3.1: 86 percent / Zn; NaBH3CN / propan-1-ol; H2O / 95 °C
4.1: pyridine / 20 °C
5.1: 1.4 g / LiHMDS / tetrahydrofuran / 1 h / -78 - 0 °C
6.1: n-BuLi / tetrahydrofuran; hexane / -78 °C
6.2: BF3*OEt2 / tetrahydrofuran; hexane / -78 - 20 °C
6.3: 90 percent / K2CO3 / methanol / 20 °C
7.1: 100 percent / 2,6-lutidine / CH2Cl2 / 0 °C
8.1: 52 percent / Et3N; Pd(PPh3)4 / toluene / Heating
9.1: 61 percent / TBAF / tetrahydrofuran / 96 h / 20 °C
View Scheme
methyl 4,6-O-benzylidene-3-O-[3-{(tert-butyldimethylsilyl)oxy}propyl]-α-D-altropyranoside
299410-95-0

methyl 4,6-O-benzylidene-3-O-[3-{(tert-butyldimethylsilyl)oxy}propyl]-α-D-altropyranoside

Eldecalcitol
104121-92-8

Eldecalcitol

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1.1: 91 percent / BaCO3; NBS / CCl4 / Heating
2.1: 86 percent / Zn; NaBH3CN / propan-1-ol; H2O / 95 °C
3.1: pyridine / 20 °C
4.1: 1.4 g / LiHMDS / tetrahydrofuran / 1 h / -78 - 0 °C
5.1: n-BuLi / tetrahydrofuran; hexane / -78 °C
5.2: BF3*OEt2 / tetrahydrofuran; hexane / -78 - 20 °C
5.3: 90 percent / K2CO3 / methanol / 20 °C
6.1: 100 percent / 2,6-lutidine / CH2Cl2 / 0 °C
7.1: 52 percent / Et3N; Pd(PPh3)4 / toluene / Heating
8.1: 61 percent / TBAF / tetrahydrofuran / 96 h / 20 °C
View Scheme
methyl 4-O-benzoyl-6-bromo-3-O-[3-{(tert-butyldimethylsilyl)oxy}propyl]-6-deoxy-α-D-altropyranoside
299410-97-2

methyl 4-O-benzoyl-6-bromo-3-O-[3-{(tert-butyldimethylsilyl)oxy}propyl]-6-deoxy-α-D-altropyranoside

Eldecalcitol
104121-92-8

Eldecalcitol

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: 86 percent / Zn; NaBH3CN / propan-1-ol; H2O / 95 °C
2.1: pyridine / 20 °C
3.1: 1.4 g / LiHMDS / tetrahydrofuran / 1 h / -78 - 0 °C
4.1: n-BuLi / tetrahydrofuran; hexane / -78 °C
4.2: BF3*OEt2 / tetrahydrofuran; hexane / -78 - 20 °C
4.3: 90 percent / K2CO3 / methanol / 20 °C
5.1: 100 percent / 2,6-lutidine / CH2Cl2 / 0 °C
6.1: 52 percent / Et3N; Pd(PPh3)4 / toluene / Heating
7.1: 61 percent / TBAF / tetrahydrofuran / 96 h / 20 °C
View Scheme
(3R,4S,5R)-3,5-bis(tert-butyldimethylsilyloxy)-4-[3-(tert-butyldimethylsilyloxy)propoxy]oct-1-en-7-yne
299411-15-7

(3R,4S,5R)-3,5-bis(tert-butyldimethylsilyloxy)-4-[3-(tert-butyldimethylsilyloxy)propoxy]oct-1-en-7-yne

Eldecalcitol
104121-92-8

Eldecalcitol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 52 percent / Et3N; Pd(PPh3)4 / toluene / Heating
2: 61 percent / TBAF / tetrahydrofuran / 96 h / 20 °C
View Scheme
methyl 2,3-anhydro-4,6-O-benzilidene-α-D-mannopyranoside
3150-15-0, 3150-16-1, 3257-59-8, 14187-71-4, 15384-57-3, 19465-13-5, 32976-15-1, 52885-37-7, 53270-02-3, 53270-03-4, 65391-11-9, 65391-12-0, 66537-92-6, 67226-04-4, 71184-14-0, 86420-78-2, 86420-79-3, 91177-51-4, 91177-52-5, 117708-93-7, 120408-72-2, 2880-96-8

methyl 2,3-anhydro-4,6-O-benzilidene-α-D-mannopyranoside

Eldecalcitol
104121-92-8

Eldecalcitol

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1.1: KOt-Bu / 110 °C
2.1: 2.1 g / Et3N; DMAP / CH2Cl2 / 3 h / 20 °C
3.1: 91 percent / BaCO3; NBS / CCl4 / Heating
4.1: 86 percent / Zn; NaBH3CN / propan-1-ol; H2O / 95 °C
5.1: pyridine / 20 °C
6.1: 1.4 g / LiHMDS / tetrahydrofuran / 1 h / -78 - 0 °C
7.1: n-BuLi / tetrahydrofuran; hexane / -78 °C
7.2: BF3*OEt2 / tetrahydrofuran; hexane / -78 - 20 °C
7.3: 90 percent / K2CO3 / methanol / 20 °C
8.1: 100 percent / 2,6-lutidine / CH2Cl2 / 0 °C
9.1: 52 percent / Et3N; Pd(PPh3)4 / toluene / Heating
10.1: 61 percent / TBAF / tetrahydrofuran / 96 h / 20 °C
View Scheme
(3R,4S,5R)-4-[3-(tert-butyldimethylsilyloxy)propoxy]oct-1-en-7-yne-3,5-diol
794516-13-5

(3R,4S,5R)-4-[3-(tert-butyldimethylsilyloxy)propoxy]oct-1-en-7-yne-3,5-diol

Eldecalcitol
104121-92-8

Eldecalcitol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 100 percent / 2,6-lutidine / CH2Cl2 / 0 °C
2: 52 percent / Et3N; Pd(PPh3)4 / toluene / Heating
3: 61 percent / TBAF / tetrahydrofuran / 96 h / 20 °C
View Scheme
(3R,4R,5R)-3-benzoyloxy-4-[3-(tert-butyldimethylsilyloxy)propoxy]-5,6-epoxyhex-1-ene
794516-11-3

(3R,4R,5R)-3-benzoyloxy-4-[3-(tert-butyldimethylsilyloxy)propoxy]-5,6-epoxyhex-1-ene

Eldecalcitol
104121-92-8

Eldecalcitol

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: n-BuLi / tetrahydrofuran; hexane / -78 °C
1.2: BF3*OEt2 / tetrahydrofuran; hexane / -78 - 20 °C
1.3: 90 percent / K2CO3 / methanol / 20 °C
2.1: 100 percent / 2,6-lutidine / CH2Cl2 / 0 °C
3.1: 52 percent / Et3N; Pd(PPh3)4 / toluene / Heating
4.1: 61 percent / TBAF / tetrahydrofuran / 96 h / 20 °C
View Scheme
(2R,3S,4R)-4-benzoyloxy-3-[3-(tert-butyldimethylsilyloxy)propoxy]hex-5-ene-1,2-diol
794516-09-9

(2R,3S,4R)-4-benzoyloxy-3-[3-(tert-butyldimethylsilyloxy)propoxy]hex-5-ene-1,2-diol

Eldecalcitol
104121-92-8

Eldecalcitol

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: pyridine / 20 °C
2.1: 1.4 g / LiHMDS / tetrahydrofuran / 1 h / -78 - 0 °C
3.1: n-BuLi / tetrahydrofuran; hexane / -78 °C
3.2: BF3*OEt2 / tetrahydrofuran; hexane / -78 - 20 °C
3.3: 90 percent / K2CO3 / methanol / 20 °C
4.1: 100 percent / 2,6-lutidine / CH2Cl2 / 0 °C
5.1: 52 percent / Et3N; Pd(PPh3)4 / toluene / Heating
6.1: 61 percent / TBAF / tetrahydrofuran / 96 h / 20 °C
View Scheme
Benzoic acid (1R,2S,3R)-2-[3-(tert-butyl-dimethyl-silanyloxy)-propoxy]-3-hydroxy-4-(2,4,6-trimethyl-benzenesulfonyloxy)-1-vinyl-butyl ester

Benzoic acid (1R,2S,3R)-2-[3-(tert-butyl-dimethyl-silanyloxy)-propoxy]-3-hydroxy-4-(2,4,6-trimethyl-benzenesulfonyloxy)-1-vinyl-butyl ester

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: 1.4 g / LiHMDS / tetrahydrofuran / 1 h / -78 - 0 °C
2.1: n-BuLi / tetrahydrofuran; hexane / -78 °C
2.2: BF3*OEt2 / tetrahydrofuran; hexane / -78 - 20 °C
2.3: 90 percent / K2CO3 / methanol / 20 °C
3.1: 100 percent / 2,6-lutidine / CH2Cl2 / 0 °C
4.1: 52 percent / Et3N; Pd(PPh3)4 / toluene / Heating
5.1: 61 percent / TBAF / tetrahydrofuran / 96 h / 20 °C
View Scheme

Eldecalcitol

Eldecalcitol

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: 57 percent / NCS; Me2S / CH2Cl2 / 0.67 h
2.1: 92 percent / imidazole / dimethylformamide / 0.25 h / 20 °C
3.1: n-BuLi / hexane; tetrahydrofuran / 0.33 h / -50 °C
4.1: 86 mg / aq. H2O2 / CHCl3 / 0.02 h
5.1: 66 percent / n-butyllithium / tetrahydrofuran; toluene / 0.5 h / -50 °C
6.1: Mg / tetrahydrofuran / 0.5 h / 20 °C
6.2: 89 percent / CuBr*Me2S / tetrahydrofuran / 0.5 h / -10 °C
7.1: 96 percent / HF/pyridine / tetrahydrofuran / 20 °C
View Scheme
(1α,2β,3β,5Z,7E,20S)-1,3-bis[(1,1-dimethylethyl)dimethyl-silyloxy]-2-[3-[(1,1-dimethylethyl)dimethylsilyloxy]propoxy]-9,10-secopregna-5,7,10(19)-triene-20-methyl 4-methylbenzenesulfonate
342645-07-2

(1α,2β,3β,5Z,7E,20S)-1,3-bis[(1,1-dimethylethyl)dimethyl-silyloxy]-2-[3-[(1,1-dimethylethyl)dimethylsilyloxy]propoxy]-9,10-secopregna-5,7,10(19)-triene-20-methyl 4-methylbenzenesulfonate

Eldecalcitol
104121-92-8

Eldecalcitol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: Mg / tetrahydrofuran / 0.5 h / 20 °C
1.2: 89 percent / CuBr*Me2S / tetrahydrofuran / 0.5 h / -10 °C
2.1: 96 percent / HF/pyridine / tetrahydrofuran / 20 °C
View Scheme
(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

Eldecalcitol
104121-92-8

Eldecalcitol

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: 97 percent / pyridinium p-toluenesulfonate; pyridinium dichromate / CH2Cl2 / 6 h / 20 °C
2.1: 66 percent / n-butyllithium / tetrahydrofuran; toluene / 0.5 h / -50 °C
3.1: Mg / tetrahydrofuran / 0.5 h / 20 °C
3.2: 89 percent / CuBr*Me2S / tetrahydrofuran / 0.5 h / -10 °C
4.1: 96 percent / HF/pyridine / tetrahydrofuran / 20 °C
View Scheme
Multi-step reaction with 4 steps
1.1: magnesium / tetrahydrofuran / 20 °C / Inert atmosphere
1.2: 18 h / -20 - 0 °C / Inert atmosphere
2.1: tetrabutylammomium bromide; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; oxone / dichloromethane / 6 h / 20 °C / Inert atmosphere
3.1: n-butyllithium / tetrahydrofuran; hexane / 0.17 h / -78 °C / Inert atmosphere
3.2: 4 h / -78 °C / Inert atmosphere
4.1: methanol / 66 h / 20 °C / Inert atmosphere
View Scheme
[3R-(1Z,3β,4α,5α)]-2-[3,5-bis[(1,1-dimethylethyl)dimethylsilyloxy]-4-[3-[(1,1-dimethylethyl)dimethylsilyloxy]propoxy]-2-methylenecyclohexylidene]-1-chloroethane
200636-50-6

[3R-(1Z,3β,4α,5α)]-2-[3,5-bis[(1,1-dimethylethyl)dimethylsilyloxy]-4-[3-[(1,1-dimethylethyl)dimethylsilyloxy]propoxy]-2-methylenecyclohexylidene]-1-chloroethane

Eldecalcitol
104121-92-8

Eldecalcitol

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: n-BuLi / hexane; tetrahydrofuran / 0.33 h / -50 °C
2.1: 86 mg / aq. H2O2 / CHCl3 / 0.02 h
3.1: 66 percent / n-butyllithium / tetrahydrofuran; toluene / 0.5 h / -50 °C
4.1: Mg / tetrahydrofuran / 0.5 h / 20 °C
4.2: 89 percent / CuBr*Me2S / tetrahydrofuran / 0.5 h / -10 °C
5.1: 96 percent / HF/pyridine / tetrahydrofuran / 20 °C
View Scheme
Multi-step reaction with 3 steps
2: H2O2
View Scheme
[3R-(1Z,3β,4α,5α)]-[2-[3,5-bis[(1,1-dimethylethyl)dimethylsilyloxy]-4-[3-[(1,1-dimethylethyl)dimethylsilyloxy]propoxy]-2-methylenecyclohexylidene]ethyl]diphenylphosphine oxide
200636-54-0

[3R-(1Z,3β,4α,5α)]-[2-[3,5-bis[(1,1-dimethylethyl)dimethylsilyloxy]-4-[3-[(1,1-dimethylethyl)dimethylsilyloxy]propoxy]-2-methylenecyclohexylidene]ethyl]diphenylphosphine oxide

Eldecalcitol
104121-92-8

Eldecalcitol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: 66 percent / n-butyllithium / tetrahydrofuran; toluene / 0.5 h / -50 °C
2.1: Mg / tetrahydrofuran / 0.5 h / 20 °C
2.2: 89 percent / CuBr*Me2S / tetrahydrofuran / 0.5 h / -10 °C
3.1: 96 percent / HF/pyridine / tetrahydrofuran / 20 °C
View Scheme
{2-[(3R,4R,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-4-[3-(tert-butyl-dimethyl-silanyloxy)-propoxy]-2-methylene-cyclohex-(Z)-ylidene]-ethyl}-diphenyl-phosphane

{2-[(3R,4R,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-4-[3-(tert-butyl-dimethyl-silanyloxy)-propoxy]-2-methylene-cyclohex-(Z)-ylidene]-ethyl}-diphenyl-phosphane

Eldecalcitol
104121-92-8

Eldecalcitol

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: 86 mg / aq. H2O2 / CHCl3 / 0.02 h
2.1: 66 percent / n-butyllithium / tetrahydrofuran; toluene / 0.5 h / -50 °C
3.1: Mg / tetrahydrofuran / 0.5 h / 20 °C
3.2: 89 percent / CuBr*Me2S / tetrahydrofuran / 0.5 h / -10 °C
4.1: 96 percent / HF/pyridine / tetrahydrofuran / 20 °C
View Scheme
Multi-step reaction with 2 steps
1: H2O2
View Scheme
[3R-(1Z,3β,4α,5α)]-2-[5-(1,1-dimethylethyl)dimethylsilyloxy-3,4-isopropylidenedioxy-2-methylenecyclohexylidene]ethanol
244278-87-3

[3R-(1Z,3β,4α,5α)]-2-[5-(1,1-dimethylethyl)dimethylsilyloxy-3,4-isopropylidenedioxy-2-methylenecyclohexylidene]ethanol

Eldecalcitol
104121-92-8

Eldecalcitol

Conditions
ConditionsYield
Multi-step reaction with 12 steps
1.1: 83 percent / pyridine; DMAP / CH2Cl2 / 1 h / 0 °C
2.1: 82 percent / CSA; (+)-10-camphorsulfonic acid / methanol / 3 h / 20 °C
3.1: 96 percent / imidazole / dimethylformamide / 3 h / 0 °C
4.1: 88 percent / Me4NOH; aq. NaOH / toluene / 72 h / 20 °C
5.1: 91 percent / LiAlH4 / tetrahydrofuran / 0.25 h / 0 °C
6.1: 57 percent / NCS; Me2S / CH2Cl2 / 0.67 h
7.1: 92 percent / imidazole / dimethylformamide / 0.25 h / 20 °C
8.1: n-BuLi / hexane; tetrahydrofuran / 0.33 h / -50 °C
9.1: 86 mg / aq. H2O2 / CHCl3 / 0.02 h
10.1: 66 percent / n-butyllithium / tetrahydrofuran; toluene / 0.5 h / -50 °C
11.1: Mg / tetrahydrofuran / 0.5 h / 20 °C
11.2: 89 percent / CuBr*Me2S / tetrahydrofuran / 0.5 h / -10 °C
12.1: 96 percent / HF/pyridine / tetrahydrofuran / 20 °C
View Scheme
Multi-step reaction with 14 steps
1.1: pyridine; dmap / dichloromethane / Inert atmosphere
2.1: water; trifluoroacetic acid / dichloromethane / 1 h / -10 °C / Inert atmosphere
3.1: 1H-imidazole / dichloromethane / 11 h / 0 °C / Inert atmosphere
4.1: pyridinium p-toluenesulfonate / dichloromethane / 36 h / 20 °C / Inert atmosphere
5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 5 h / 70 °C / Inert atmosphere
6.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 6 h / Reflux; Inert atmosphere
7.1: acetic acid; water / tetrahydrofuran / 14 h / 40 °C / Inert atmosphere
8.1: water; tetramethyl ammoniumhydroxide; sodium hydroxide / toluene / 20 h / 20 °C / Inert atmosphere
9.1: lithium aluminium tetrahydride / tetrahydrofuran / 0 °C / Inert atmosphere
10.1: N-chloro-succinimide; dimethylsulfide / dichloromethane / 0.5 h / 0 °C / Inert atmosphere
11.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 3 h / 20 °C / Inert atmosphere
12.1: lithium hexamethyldisilazane / tetrahydrofuran; dichloromethane / 3 h / -78 - 20 °C / Inert atmosphere
12.2: 13 h / 20 °C / Inert atmosphere
13.1: n-butyllithium / tetrahydrofuran; hexane / 0.17 h / -78 °C / Inert atmosphere
13.2: 4 h / -78 °C / Inert atmosphere
14.1: methanol / 66 h / 20 °C / Inert atmosphere
View Scheme
[3R-(1Z,3β,4α,5α)]-2-[3,4,5-trihydroxy-2-methylenecyclohexylidene]ethyl trimethylacetate
377091-68-4

[3R-(1Z,3β,4α,5α)]-2-[3,4,5-trihydroxy-2-methylenecyclohexylidene]ethyl trimethylacetate

Eldecalcitol
104121-92-8

Eldecalcitol

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1.1: 96 percent / imidazole / dimethylformamide / 3 h / 0 °C
2.1: 88 percent / Me4NOH; aq. NaOH / toluene / 72 h / 20 °C
3.1: 91 percent / LiAlH4 / tetrahydrofuran / 0.25 h / 0 °C
4.1: 57 percent / NCS; Me2S / CH2Cl2 / 0.67 h
5.1: 92 percent / imidazole / dimethylformamide / 0.25 h / 20 °C
6.1: n-BuLi / hexane; tetrahydrofuran / 0.33 h / -50 °C
7.1: 86 mg / aq. H2O2 / CHCl3 / 0.02 h
8.1: 66 percent / n-butyllithium / tetrahydrofuran; toluene / 0.5 h / -50 °C
9.1: Mg / tetrahydrofuran / 0.5 h / 20 °C
9.2: 89 percent / CuBr*Me2S / tetrahydrofuran / 0.5 h / -10 °C
10.1: 96 percent / HF/pyridine / tetrahydrofuran / 20 °C
View Scheme
[3R-(1Z,3β,4α,5α)]-2-[5-(1,1-dimethylethyl)dimethylsilyloxy-3,4-isopropylidenedioxy-2-methylenecyclohexylidene]ethyl trimethylacetate
342644-83-1

[3R-(1Z,3β,4α,5α)]-2-[5-(1,1-dimethylethyl)dimethylsilyloxy-3,4-isopropylidenedioxy-2-methylenecyclohexylidene]ethyl trimethylacetate

Eldecalcitol
104121-92-8

Eldecalcitol

Conditions
ConditionsYield
Multi-step reaction with 11 steps
1.1: 82 percent / CSA; (+)-10-camphorsulfonic acid / methanol / 3 h / 20 °C
2.1: 96 percent / imidazole / dimethylformamide / 3 h / 0 °C
3.1: 88 percent / Me4NOH; aq. NaOH / toluene / 72 h / 20 °C
4.1: 91 percent / LiAlH4 / tetrahydrofuran / 0.25 h / 0 °C
5.1: 57 percent / NCS; Me2S / CH2Cl2 / 0.67 h
6.1: 92 percent / imidazole / dimethylformamide / 0.25 h / 20 °C
7.1: n-BuLi / hexane; tetrahydrofuran / 0.33 h / -50 °C
8.1: 86 mg / aq. H2O2 / CHCl3 / 0.02 h
9.1: 66 percent / n-butyllithium / tetrahydrofuran; toluene / 0.5 h / -50 °C
10.1: Mg / tetrahydrofuran / 0.5 h / 20 °C
10.2: 89 percent / CuBr*Me2S / tetrahydrofuran / 0.5 h / -10 °C
11.1: 96 percent / HF/pyridine / tetrahydrofuran / 20 °C
View Scheme
Multi-step reaction with 13 steps
1.1: water; trifluoroacetic acid / dichloromethane / 1 h / -10 °C / Inert atmosphere
2.1: 1H-imidazole / dichloromethane / 11 h / 0 °C / Inert atmosphere
3.1: pyridinium p-toluenesulfonate / dichloromethane / 36 h / 20 °C / Inert atmosphere
4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 5 h / 70 °C / Inert atmosphere
5.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 6 h / Reflux; Inert atmosphere
6.1: acetic acid; water / tetrahydrofuran / 14 h / 40 °C / Inert atmosphere
7.1: water; tetramethyl ammoniumhydroxide; sodium hydroxide / toluene / 20 h / 20 °C / Inert atmosphere
8.1: lithium aluminium tetrahydride / tetrahydrofuran / 0 °C / Inert atmosphere
9.1: N-chloro-succinimide; dimethylsulfide / dichloromethane / 0.5 h / 0 °C / Inert atmosphere
10.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 3 h / 20 °C / Inert atmosphere
11.1: lithium hexamethyldisilazane / tetrahydrofuran; dichloromethane / 3 h / -78 - 20 °C / Inert atmosphere
11.2: 13 h / 20 °C / Inert atmosphere
12.1: n-butyllithium / tetrahydrofuran; hexane / 0.17 h / -78 °C / Inert atmosphere
12.2: 4 h / -78 °C / Inert atmosphere
13.1: methanol / 66 h / 20 °C / Inert atmosphere
View Scheme
(1β,2α,3α,5Z,7E)-1,3-bis[(1,1-dimethylethyl)dimethylsilyloxy]-2-[3-[(1,1-dimethylethyl)dimethylsilyloxy]propoxy]-25-trimethylsilyloxy-9,10-secocholesta-5,7,10(19)-triene
342645-84-5

(1β,2α,3α,5Z,7E)-1,3-bis[(1,1-dimethylethyl)dimethylsilyloxy]-2-[3-[(1,1-dimethylethyl)dimethylsilyloxy]propoxy]-25-trimethylsilyloxy-9,10-secocholesta-5,7,10(19)-triene

Eldecalcitol
104121-92-8

Eldecalcitol

Conditions
ConditionsYield
With pyridine; hydrogen fluoride In tetrahydrofuran at 20℃;96%
C54H106O5Si4

C54H106O5Si4

Eldecalcitol
104121-92-8

Eldecalcitol

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride In tetrahydrofuran at 25℃;89%
((1R,2R,3R,Z)-2-(3-(tert-butyldiphenylsilyloxy)propoxy)-5-((E)-2-((1R,3aS,7aR)-7a-methyl-1-((R)-6-methyl-6-(trimethylsilyloxy)heptan-2-yl)dihydro-1H-indene-4(2H,5H,6H,7H,7aH)-ylidene)ethylidene)-4-methylene cyclohexane-1,3-diyl)bis(oxy)bis(tert-butyldimethylsilane)

((1R,2R,3R,Z)-2-(3-(tert-butyldiphenylsilyloxy)propoxy)-5-((E)-2-((1R,3aS,7aR)-7a-methyl-1-((R)-6-methyl-6-(trimethylsilyloxy)heptan-2-yl)dihydro-1H-indene-4(2H,5H,6H,7H,7aH)-ylidene)ethylidene)-4-methylene cyclohexane-1,3-diyl)bis(oxy)bis(tert-butyldimethylsilane)

Eldecalcitol
104121-92-8

Eldecalcitol

Conditions
ConditionsYield
With toluene-4-sulfonic acid In methanol; dichloromethane at 20℃; for 5h; Inert atmosphere;80%
C38H66O9

C38H66O9

Eldecalcitol
104121-92-8

Eldecalcitol

Conditions
ConditionsYield
With methanol at 20℃; for 66h; Inert atmosphere; stereoselective reaction;68%
(R)-6-{(1R,3aS,7aR)-4-[2-[(3R,4R,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-4-[3-(tert-butyl-dimethyl-silanyloxy)-propoxy]-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-2-methyl-heptan-2-ol

(R)-6-{(1R,3aS,7aR)-4-[2-[(3R,4R,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-4-[3-(tert-butyl-dimethyl-silanyloxy)-propoxy]-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-2-methyl-heptan-2-ol

Eldecalcitol
104121-92-8

Eldecalcitol

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃; for 96h;61%
(5Z,7E)-(1R,2R,3R)-1,3-bis(tert-butyldimethylsilyloxy)-2-(3-tert-butyldimethylsilyloxypropoxy)-25-triethylsilyloxy-9,10-secocholesta-5,7,10(19)-triene
933779-95-4

(5Z,7E)-(1R,2R,3R)-1,3-bis(tert-butyldimethylsilyloxy)-2-(3-tert-butyldimethylsilyloxypropoxy)-25-triethylsilyloxy-9,10-secocholesta-5,7,10(19)-triene

Eldecalcitol
104121-92-8

Eldecalcitol

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride In tetrahydrofuran; toluene at 105℃; for 2h;60%
(5R,6R)-6-((R)-1-(methoxymethoxy)allyl)-5-(prop-2-yn-1-yl)-2,4,7,11,13-pentaoxatetradecane

(5R,6R)-6-((R)-1-(methoxymethoxy)allyl)-5-(prop-2-yn-1-yl)-2,4,7,11,13-pentaoxatetradecane

C21H37BrO2

C21H37BrO2

Eldecalcitol
104121-92-8

Eldecalcitol

Conditions
ConditionsYield
Stage #1: (5R,6R)-6-((R)-1-(methoxymethoxy)allyl)-5-(prop-2-yn-1-yl)-2,4,7,11,13-pentaoxatetradecane; C21H37BrO2 With tetrakis(triphenylphosphine) palladium(0); triethylamine In toluene at 110℃; for 2h;
Stage #2: With camphor-10-sulfonic acid In methanol at 20℃; for 72h;		36%
25-[(triethylsilyl)oxy]de-A,B-cholestan-8-one
144848-24-8

25-[(triethylsilyl)oxy]de-A,B-cholestan-8-one

[3R-(1Z,3β,4α,5α)]-[2-[3,5-bis[(1,1-dimethylethyl)dimethylsilyloxy]-4-[3-[(1,1-dimethylethyl)dimethylsilyloxy]propoxy]-2-methylenecyclohexylidene]ethyl]diphenylphosphine oxide
200636-54-0

[3R-(1Z,3β,4α,5α)]-[2-[3,5-bis[(1,1-dimethylethyl)dimethylsilyloxy]-4-[3-[(1,1-dimethylethyl)dimethylsilyloxy]propoxy]-2-methylenecyclohexylidene]ethyl]diphenylphosphine oxide

Eldecalcitol
104121-92-8

Eldecalcitol

Conditions
ConditionsYield
Multistep reaction;
methyl 4,6-O-benzylidene-3-O-(3-hydroxypropyl)-α-D-altropyranoside
299410-93-8

methyl 4,6-O-benzylidene-3-O-(3-hydroxypropyl)-α-D-altropyranoside

Eldecalcitol
104121-92-8

Eldecalcitol

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1.1: 2.1 g / Et3N; DMAP / CH2Cl2 / 3 h / 20 °C
2.1: 91 percent / BaCO3; NBS / CCl4 / Heating
3.1: 86 percent / Zn; NaBH3CN / propan-1-ol; H2O / 95 °C
4.1: pyridine / 20 °C
5.1: 1.4 g / LiHMDS / tetrahydrofuran / 1 h / -78 - 0 °C
6.1: n-BuLi / tetrahydrofuran; hexane / -78 °C
6.2: BF3*OEt2 / tetrahydrofuran; hexane / -78 - 20 °C
6.3: 90 percent / K2CO3 / methanol / 20 °C
7.1: 100 percent / 2,6-lutidine / CH2Cl2 / 0 °C
8.1: 52 percent / Et3N; Pd(PPh3)4 / toluene / Heating
9.1: 61 percent / TBAF / tetrahydrofuran / 96 h / 20 °C
View Scheme
methyl 4,6-O-benzylidene-3-O-[3-{(tert-butyldimethylsilyl)oxy}propyl]-α-D-altropyranoside
299410-95-0

methyl 4,6-O-benzylidene-3-O-[3-{(tert-butyldimethylsilyl)oxy}propyl]-α-D-altropyranoside

Eldecalcitol
104121-92-8

Eldecalcitol

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1.1: 91 percent / BaCO3; NBS / CCl4 / Heating
2.1: 86 percent / Zn; NaBH3CN / propan-1-ol; H2O / 95 °C
3.1: pyridine / 20 °C
4.1: 1.4 g / LiHMDS / tetrahydrofuran / 1 h / -78 - 0 °C
5.1: n-BuLi / tetrahydrofuran; hexane / -78 °C
5.2: BF3*OEt2 / tetrahydrofuran; hexane / -78 - 20 °C
5.3: 90 percent / K2CO3 / methanol / 20 °C
6.1: 100 percent / 2,6-lutidine / CH2Cl2 / 0 °C
7.1: 52 percent / Et3N; Pd(PPh3)4 / toluene / Heating
8.1: 61 percent / TBAF / tetrahydrofuran / 96 h / 20 °C
View Scheme
methyl 4-O-benzoyl-6-bromo-3-O-[3-{(tert-butyldimethylsilyl)oxy}propyl]-6-deoxy-α-D-altropyranoside
299410-97-2

methyl 4-O-benzoyl-6-bromo-3-O-[3-{(tert-butyldimethylsilyl)oxy}propyl]-6-deoxy-α-D-altropyranoside

Eldecalcitol
104121-92-8

Eldecalcitol

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: 86 percent / Zn; NaBH3CN / propan-1-ol; H2O / 95 °C
2.1: pyridine / 20 °C
3.1: 1.4 g / LiHMDS / tetrahydrofuran / 1 h / -78 - 0 °C
4.1: n-BuLi / tetrahydrofuran; hexane / -78 °C
4.2: BF3*OEt2 / tetrahydrofuran; hexane / -78 - 20 °C
4.3: 90 percent / K2CO3 / methanol / 20 °C
5.1: 100 percent / 2,6-lutidine / CH2Cl2 / 0 °C
6.1: 52 percent / Et3N; Pd(PPh3)4 / toluene / Heating
7.1: 61 percent / TBAF / tetrahydrofuran / 96 h / 20 °C
View Scheme
(3R,4S,5R)-3,5-bis(tert-butyldimethylsilyloxy)-4-[3-(tert-butyldimethylsilyloxy)propoxy]oct-1-en-7-yne
299411-15-7

(3R,4S,5R)-3,5-bis(tert-butyldimethylsilyloxy)-4-[3-(tert-butyldimethylsilyloxy)propoxy]oct-1-en-7-yne

Eldecalcitol
104121-92-8

Eldecalcitol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 52 percent / Et3N; Pd(PPh3)4 / toluene / Heating
2: 61 percent / TBAF / tetrahydrofuran / 96 h / 20 °C
View Scheme
methyl 2,3-anhydro-4,6-O-benzilidene-α-D-mannopyranoside
3150-15-0, 3150-16-1, 3257-59-8, 14187-71-4, 15384-57-3, 19465-13-5, 32976-15-1, 52885-37-7, 53270-02-3, 53270-03-4, 65391-11-9, 65391-12-0, 66537-92-6, 67226-04-4, 71184-14-0, 86420-78-2, 86420-79-3, 91177-51-4, 91177-52-5, 117708-93-7, 120408-72-2, 2880-96-8

methyl 2,3-anhydro-4,6-O-benzilidene-α-D-mannopyranoside

Eldecalcitol
104121-92-8

Eldecalcitol

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1.1: KOt-Bu / 110 °C
2.1: 2.1 g / Et3N; DMAP / CH2Cl2 / 3 h / 20 °C
3.1: 91 percent / BaCO3; NBS / CCl4 / Heating
4.1: 86 percent / Zn; NaBH3CN / propan-1-ol; H2O / 95 °C
5.1: pyridine / 20 °C
6.1: 1.4 g / LiHMDS / tetrahydrofuran / 1 h / -78 - 0 °C
7.1: n-BuLi / tetrahydrofuran; hexane / -78 °C
7.2: BF3*OEt2 / tetrahydrofuran; hexane / -78 - 20 °C
7.3: 90 percent / K2CO3 / methanol / 20 °C
8.1: 100 percent / 2,6-lutidine / CH2Cl2 / 0 °C
9.1: 52 percent / Et3N; Pd(PPh3)4 / toluene / Heating
10.1: 61 percent / TBAF / tetrahydrofuran / 96 h / 20 °C
View Scheme
(3R,4S,5R)-4-[3-(tert-butyldimethylsilyloxy)propoxy]oct-1-en-7-yne-3,5-diol
794516-13-5

(3R,4S,5R)-4-[3-(tert-butyldimethylsilyloxy)propoxy]oct-1-en-7-yne-3,5-diol

Eldecalcitol
104121-92-8

Eldecalcitol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 100 percent / 2,6-lutidine / CH2Cl2 / 0 °C
2: 52 percent / Et3N; Pd(PPh3)4 / toluene / Heating
3: 61 percent / TBAF / tetrahydrofuran / 96 h / 20 °C
View Scheme
(3R,4R,5R)-3-benzoyloxy-4-[3-(tert-butyldimethylsilyloxy)propoxy]-5,6-epoxyhex-1-ene
794516-11-3

(3R,4R,5R)-3-benzoyloxy-4-[3-(tert-butyldimethylsilyloxy)propoxy]-5,6-epoxyhex-1-ene

Eldecalcitol
104121-92-8

Eldecalcitol

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: n-BuLi / tetrahydrofuran; hexane / -78 °C
1.2: BF3*OEt2 / tetrahydrofuran; hexane / -78 - 20 °C
1.3: 90 percent / K2CO3 / methanol / 20 °C
2.1: 100 percent / 2,6-lutidine / CH2Cl2 / 0 °C
3.1: 52 percent / Et3N; Pd(PPh3)4 / toluene / Heating
4.1: 61 percent / TBAF / tetrahydrofuran / 96 h / 20 °C
View Scheme
(2R,3S,4R)-4-benzoyloxy-3-[3-(tert-butyldimethylsilyloxy)propoxy]hex-5-ene-1,2-diol
794516-09-9

(2R,3S,4R)-4-benzoyloxy-3-[3-(tert-butyldimethylsilyloxy)propoxy]hex-5-ene-1,2-diol

Eldecalcitol
104121-92-8

Eldecalcitol

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: pyridine / 20 °C
2.1: 1.4 g / LiHMDS / tetrahydrofuran / 1 h / -78 - 0 °C
3.1: n-BuLi / tetrahydrofuran; hexane / -78 °C
3.2: BF3*OEt2 / tetrahydrofuran; hexane / -78 - 20 °C
3.3: 90 percent / K2CO3 / methanol / 20 °C
4.1: 100 percent / 2,6-lutidine / CH2Cl2 / 0 °C
5.1: 52 percent / Et3N; Pd(PPh3)4 / toluene / Heating
6.1: 61 percent / TBAF / tetrahydrofuran / 96 h / 20 °C
View Scheme
Benzoic acid (1R,2S,3R)-2-[3-(tert-butyl-dimethyl-silanyloxy)-propoxy]-3-hydroxy-4-(2,4,6-trimethyl-benzenesulfonyloxy)-1-vinyl-butyl ester

Benzoic acid (1R,2S,3R)-2-[3-(tert-butyl-dimethyl-silanyloxy)-propoxy]-3-hydroxy-4-(2,4,6-trimethyl-benzenesulfonyloxy)-1-vinyl-butyl ester

Eldecalcitol
104121-92-8

Eldecalcitol

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: 1.4 g / LiHMDS / tetrahydrofuran / 1 h / -78 - 0 °C
2.1: n-BuLi / tetrahydrofuran; hexane / -78 °C
2.2: BF3*OEt2 / tetrahydrofuran; hexane / -78 - 20 °C
2.3: 90 percent / K2CO3 / methanol / 20 °C
3.1: 100 percent / 2,6-lutidine / CH2Cl2 / 0 °C
4.1: 52 percent / Et3N; Pd(PPh3)4 / toluene / Heating
5.1: 61 percent / TBAF / tetrahydrofuran / 96 h / 20 °C
View Scheme
[3R-(1Z,3β,4α,5α)]-2-[3,5-bis[(1,1-dimethylethyl)dimethylsilyloxy]-4-(3-hydroxypropoxy)-2-methylenecyclohexylidene]ethanol
342644-91-1

[3R-(1Z,3β,4α,5α)]-2-[3,5-bis[(1,1-dimethylethyl)dimethylsilyloxy]-4-(3-hydroxypropoxy)-2-methylenecyclohexylidene]ethanol

Eldecalcitol
104121-92-8

Eldecalcitol

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: 57 percent / NCS; Me2S / CH2Cl2 / 0.67 h
2.1: 92 percent / imidazole / dimethylformamide / 0.25 h / 20 °C
3.1: n-BuLi / hexane; tetrahydrofuran / 0.33 h / -50 °C
4.1: 86 mg / aq. H2O2 / CHCl3 / 0.02 h
5.1: 66 percent / n-butyllithium / tetrahydrofuran; toluene / 0.5 h / -50 °C
6.1: Mg / tetrahydrofuran / 0.5 h / 20 °C
6.2: 89 percent / CuBr*Me2S / tetrahydrofuran / 0.5 h / -10 °C
7.1: 96 percent / HF/pyridine / tetrahydrofuran / 20 °C
View Scheme
(1α,2β,3β,5Z,7E,20S)-1,3-bis[(1,1-dimethylethyl)dimethyl-silyloxy]-2-[3-[(1,1-dimethylethyl)dimethylsilyloxy]propoxy]-9,10-secopregna-5,7,10(19)-triene-20-methyl 4-methylbenzenesulfonate
342645-07-2

(1α,2β,3β,5Z,7E,20S)-1,3-bis[(1,1-dimethylethyl)dimethyl-silyloxy]-2-[3-[(1,1-dimethylethyl)dimethylsilyloxy]propoxy]-9,10-secopregna-5,7,10(19)-triene-20-methyl 4-methylbenzenesulfonate

Eldecalcitol
104121-92-8

Eldecalcitol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: Mg / tetrahydrofuran / 0.5 h / 20 °C
1.2: 89 percent / CuBr*Me2S / tetrahydrofuran / 0.5 h / -10 °C
2.1: 96 percent / HF/pyridine / tetrahydrofuran / 20 °C
View Scheme
(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

Eldecalcitol
104121-92-8

Eldecalcitol

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: 97 percent / pyridinium p-toluenesulfonate; pyridinium dichromate / CH2Cl2 / 6 h / 20 °C
2.1: 66 percent / n-butyllithium / tetrahydrofuran; toluene / 0.5 h / -50 °C
3.1: Mg / tetrahydrofuran / 0.5 h / 20 °C
3.2: 89 percent / CuBr*Me2S / tetrahydrofuran / 0.5 h / -10 °C
4.1: 96 percent / HF/pyridine / tetrahydrofuran / 20 °C
View Scheme
Multi-step reaction with 4 steps
1.1: magnesium / tetrahydrofuran / 20 °C / Inert atmosphere
1.2: 18 h / -20 - 0 °C / Inert atmosphere
2.1: tetrabutylammomium bromide; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; oxone / dichloromethane / 6 h / 20 °C / Inert atmosphere
3.1: n-butyllithium / tetrahydrofuran; hexane / 0.17 h / -78 °C / Inert atmosphere
3.2: 4 h / -78 °C / Inert atmosphere
4.1: methanol / 66 h / 20 °C / Inert atmosphere
View Scheme
[3R-(1Z,3β,4α,5α)]-2-[3,5-bis[(1,1-dimethylethyl)dimethylsilyloxy]-4-[3-[(1,1-dimethylethyl)dimethylsilyloxy]propoxy]-2-methylenecyclohexylidene]-1-chloroethane
200636-50-6

[3R-(1Z,3β,4α,5α)]-2-[3,5-bis[(1,1-dimethylethyl)dimethylsilyloxy]-4-[3-[(1,1-dimethylethyl)dimethylsilyloxy]propoxy]-2-methylenecyclohexylidene]-1-chloroethane

Eldecalcitol
104121-92-8

Eldecalcitol

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: n-BuLi / hexane; tetrahydrofuran / 0.33 h / -50 °C
2.1: 86 mg / aq. H2O2 / CHCl3 / 0.02 h
3.1: 66 percent / n-butyllithium / tetrahydrofuran; toluene / 0.5 h / -50 °C
4.1: Mg / tetrahydrofuran / 0.5 h / 20 °C
4.2: 89 percent / CuBr*Me2S / tetrahydrofuran / 0.5 h / -10 °C
5.1: 96 percent / HF/pyridine / tetrahydrofuran / 20 °C
View Scheme
Multi-step reaction with 3 steps
2: H2O2
View Scheme
[3R-(1Z,3β,4α,5α)]-[2-[3,5-bis[(1,1-dimethylethyl)dimethylsilyloxy]-4-[3-[(1,1-dimethylethyl)dimethylsilyloxy]propoxy]-2-methylenecyclohexylidene]ethyl]diphenylphosphine oxide
200636-54-0

[3R-(1Z,3β,4α,5α)]-[2-[3,5-bis[(1,1-dimethylethyl)dimethylsilyloxy]-4-[3-[(1,1-dimethylethyl)dimethylsilyloxy]propoxy]-2-methylenecyclohexylidene]ethyl]diphenylphosphine oxide

Eldecalcitol
104121-92-8

Eldecalcitol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: 66 percent / n-butyllithium / tetrahydrofuran; toluene / 0.5 h / -50 °C
2.1: Mg / tetrahydrofuran / 0.5 h / 20 °C
2.2: 89 percent / CuBr*Me2S / tetrahydrofuran / 0.5 h / -10 °C
3.1: 96 percent / HF/pyridine / tetrahydrofuran / 20 °C
View Scheme
{2-[(3R,4R,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-4-[3-(tert-butyl-dimethyl-silanyloxy)-propoxy]-2-methylene-cyclohex-(Z)-ylidene]-ethyl}-diphenyl-phosphane

{2-[(3R,4R,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-4-[3-(tert-butyl-dimethyl-silanyloxy)-propoxy]-2-methylene-cyclohex-(Z)-ylidene]-ethyl}-diphenyl-phosphane

Eldecalcitol
104121-92-8

Eldecalcitol

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: 86 mg / aq. H2O2 / CHCl3 / 0.02 h
2.1: 66 percent / n-butyllithium / tetrahydrofuran; toluene / 0.5 h / -50 °C
3.1: Mg / tetrahydrofuran / 0.5 h / 20 °C
3.2: 89 percent / CuBr*Me2S / tetrahydrofuran / 0.5 h / -10 °C
4.1: 96 percent / HF/pyridine / tetrahydrofuran / 20 °C
View Scheme
Multi-step reaction with 2 steps
1: H2O2
View Scheme
[3R-(1Z,3β,4α,5α)]-2-[5-(1,1-dimethylethyl)dimethylsilyloxy-3,4-isopropylidenedioxy-2-methylenecyclohexylidene]ethanol
244278-87-3

[3R-(1Z,3β,4α,5α)]-2-[5-(1,1-dimethylethyl)dimethylsilyloxy-3,4-isopropylidenedioxy-2-methylenecyclohexylidene]ethanol

Eldecalcitol
104121-92-8

Eldecalcitol

Conditions
ConditionsYield
Multi-step reaction with 12 steps
1.1: 83 percent / pyridine; DMAP / CH2Cl2 / 1 h / 0 °C
2.1: 82 percent / CSA; (+)-10-camphorsulfonic acid / methanol / 3 h / 20 °C
3.1: 96 percent / imidazole / dimethylformamide / 3 h / 0 °C
4.1: 88 percent / Me4NOH; aq. NaOH / toluene / 72 h / 20 °C
5.1: 91 percent / LiAlH4 / tetrahydrofuran / 0.25 h / 0 °C
6.1: 57 percent / NCS; Me2S / CH2Cl2 / 0.67 h
7.1: 92 percent / imidazole / dimethylformamide / 0.25 h / 20 °C
8.1: n-BuLi / hexane; tetrahydrofuran / 0.33 h / -50 °C
9.1: 86 mg / aq. H2O2 / CHCl3 / 0.02 h
10.1: 66 percent / n-butyllithium / tetrahydrofuran; toluene / 0.5 h / -50 °C
11.1: Mg / tetrahydrofuran / 0.5 h / 20 °C
11.2: 89 percent / CuBr*Me2S / tetrahydrofuran / 0.5 h / -10 °C
12.1: 96 percent / HF/pyridine / tetrahydrofuran / 20 °C
View Scheme
Multi-step reaction with 14 steps
1.1: pyridine; dmap / dichloromethane / Inert atmosphere
2.1: water; trifluoroacetic acid / dichloromethane / 1 h / -10 °C / Inert atmosphere
3.1: 1H-imidazole / dichloromethane / 11 h / 0 °C / Inert atmosphere
4.1: pyridinium p-toluenesulfonate / dichloromethane / 36 h / 20 °C / Inert atmosphere
5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 5 h / 70 °C / Inert atmosphere
6.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 6 h / Reflux; Inert atmosphere
7.1: acetic acid; water / tetrahydrofuran / 14 h / 40 °C / Inert atmosphere
8.1: water; tetramethyl ammoniumhydroxide; sodium hydroxide / toluene / 20 h / 20 °C / Inert atmosphere
9.1: lithium aluminium tetrahydride / tetrahydrofuran / 0 °C / Inert atmosphere
10.1: N-chloro-succinimide; dimethylsulfide / dichloromethane / 0.5 h / 0 °C / Inert atmosphere
11.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 3 h / 20 °C / Inert atmosphere
12.1: lithium hexamethyldisilazane / tetrahydrofuran; dichloromethane / 3 h / -78 - 20 °C / Inert atmosphere
12.2: 13 h / 20 °C / Inert atmosphere
13.1: n-butyllithium / tetrahydrofuran; hexane / 0.17 h / -78 °C / Inert atmosphere
13.2: 4 h / -78 °C / Inert atmosphere
14.1: methanol / 66 h / 20 °C / Inert atmosphere
View Scheme
[3R-(1Z,3β,4α,5α)]-2-[3,4,5-trihydroxy-2-methylenecyclohexylidene]ethyl trimethylacetate
377091-68-4

[3R-(1Z,3β,4α,5α)]-2-[3,4,5-trihydroxy-2-methylenecyclohexylidene]ethyl trimethylacetate

Eldecalcitol
104121-92-8

Eldecalcitol

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1.1: 96 percent / imidazole / dimethylformamide / 3 h / 0 °C
2.1: 88 percent / Me4NOH; aq. NaOH / toluene / 72 h / 20 °C
3.1: 91 percent / LiAlH4 / tetrahydrofuran / 0.25 h / 0 °C
4.1: 57 percent / NCS; Me2S / CH2Cl2 / 0.67 h
5.1: 92 percent / imidazole / dimethylformamide / 0.25 h / 20 °C
6.1: n-BuLi / hexane; tetrahydrofuran / 0.33 h / -50 °C
7.1: 86 mg / aq. H2O2 / CHCl3 / 0.02 h
8.1: 66 percent / n-butyllithium / tetrahydrofuran; toluene / 0.5 h / -50 °C
9.1: Mg / tetrahydrofuran / 0.5 h / 20 °C
9.2: 89 percent / CuBr*Me2S / tetrahydrofuran / 0.5 h / -10 °C
10.1: 96 percent / HF/pyridine / tetrahydrofuran / 20 °C
View Scheme
[3R-(1Z,3β,4α,5α)]-2-[5-(1,1-dimethylethyl)dimethylsilyloxy-3,4-isopropylidenedioxy-2-methylenecyclohexylidene]ethyl trimethylacetate
342644-83-1

[3R-(1Z,3β,4α,5α)]-2-[5-(1,1-dimethylethyl)dimethylsilyloxy-3,4-isopropylidenedioxy-2-methylenecyclohexylidene]ethyl trimethylacetate

Eldecalcitol
104121-92-8

Eldecalcitol

Conditions
ConditionsYield
Multi-step reaction with 11 steps
1.1: 82 percent / CSA; (+)-10-camphorsulfonic acid / methanol / 3 h / 20 °C
2.1: 96 percent / imidazole / dimethylformamide / 3 h / 0 °C
3.1: 88 percent / Me4NOH; aq. NaOH / toluene / 72 h / 20 °C
4.1: 91 percent / LiAlH4 / tetrahydrofuran / 0.25 h / 0 °C
5.1: 57 percent / NCS; Me2S / CH2Cl2 / 0.67 h
6.1: 92 percent / imidazole / dimethylformamide / 0.25 h / 20 °C
7.1: n-BuLi / hexane; tetrahydrofuran / 0.33 h / -50 °C
8.1: 86 mg / aq. H2O2 / CHCl3 / 0.02 h
9.1: 66 percent / n-butyllithium / tetrahydrofuran; toluene / 0.5 h / -50 °C
10.1: Mg / tetrahydrofuran / 0.5 h / 20 °C
10.2: 89 percent / CuBr*Me2S / tetrahydrofuran / 0.5 h / -10 °C
11.1: 96 percent / HF/pyridine / tetrahydrofuran / 20 °C
View Scheme
Multi-step reaction with 13 steps
1.1: water; trifluoroacetic acid / dichloromethane / 1 h / -10 °C / Inert atmosphere
2.1: 1H-imidazole / dichloromethane / 11 h / 0 °C / Inert atmosphere
3.1: pyridinium p-toluenesulfonate / dichloromethane / 36 h / 20 °C / Inert atmosphere
4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 5 h / 70 °C / Inert atmosphere
5.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 6 h / Reflux; Inert atmosphere
6.1: acetic acid; water / tetrahydrofuran / 14 h / 40 °C / Inert atmosphere
7.1: water; tetramethyl ammoniumhydroxide; sodium hydroxide / toluene / 20 h / 20 °C / Inert atmosphere
8.1: lithium aluminium tetrahydride / tetrahydrofuran / 0 °C / Inert atmosphere
9.1: N-chloro-succinimide; dimethylsulfide / dichloromethane / 0.5 h / 0 °C / Inert atmosphere
10.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 3 h / 20 °C / Inert atmosphere
11.1: lithium hexamethyldisilazane / tetrahydrofuran; dichloromethane / 3 h / -78 - 20 °C / Inert atmosphere
11.2: 13 h / 20 °C / Inert atmosphere
12.1: n-butyllithium / tetrahydrofuran; hexane / 0.17 h / -78 °C / Inert atmosphere
12.2: 4 h / -78 °C / Inert atmosphere
13.1: methanol / 66 h / 20 °C / Inert atmosphere
View Scheme
[3R-(1Z,3β,4α,5α)]-2-[3,5-bis[(1,1-dimethylethyl)dimethylsilyloxy]-4-hydroxy-2-methylenecyclohexylidene]ethyl trimethylacetate
342644-90-0

[3R-(1Z,3β,4α,5α)]-2-[3,5-bis[(1,1-dimethylethyl)dimethylsilyloxy]-4-hydroxy-2-methylenecyclohexylidene]ethyl trimethylacetate

Eldecalcitol
104121-92-8

Eldecalcitol

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1.1: 88 percent / Me4NOH; aq. NaOH / toluene / 72 h / 20 °C
2.1: 91 percent / LiAlH4 / tetrahydrofuran / 0.25 h / 0 °C
3.1: 57 percent / NCS; Me2S / CH2Cl2 / 0.67 h
4.1: 92 percent / imidazole / dimethylformamide / 0.25 h / 20 °C
5.1: n-BuLi / hexane; tetrahydrofuran / 0.33 h / -50 °C
6.1: 86 mg / aq. H2O2 / CHCl3 / 0.02 h
7.1: 66 percent / n-butyllithium / tetrahydrofuran; toluene / 0.5 h / -50 °C
8.1: Mg / tetrahydrofuran / 0.5 h / 20 °C
8.2: 89 percent / CuBr*Me2S / tetrahydrofuran / 0.5 h / -10 °C
9.1: 96 percent / HF/pyridine / tetrahydrofuran / 20 °C
View Scheme
Multi-step reaction with 11 steps
1.1: pyridinium p-toluenesulfonate / dichloromethane / 36 h / 20 °C / Inert atmosphere
2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 5 h / 70 °C / Inert atmosphere
3.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 6 h / Reflux; Inert atmosphere
4.1: acetic acid; water / tetrahydrofuran / 14 h / 40 °C / Inert atmosphere
5.1: water; tetramethyl ammoniumhydroxide; sodium hydroxide / toluene / 20 h / 20 °C / Inert atmosphere
6.1: lithium aluminium tetrahydride / tetrahydrofuran / 0 °C / Inert atmosphere
7.1: N-chloro-succinimide; dimethylsulfide / dichloromethane / 0.5 h / 0 °C / Inert atmosphere
8.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 3 h / 20 °C / Inert atmosphere
9.1: lithium hexamethyldisilazane / tetrahydrofuran; dichloromethane / 3 h / -78 - 20 °C / Inert atmosphere
9.2: 13 h / 20 °C / Inert atmosphere
10.1: n-butyllithium / tetrahydrofuran; hexane / 0.17 h / -78 °C / Inert atmosphere
10.2: 4 h / -78 °C / Inert atmosphere
11.1: methanol / 66 h / 20 °C / Inert atmosphere
View Scheme
[3R-(1Z,3β,4α,5α)]-2-[3,5-bis[(1,1-dimethylethyl)dimethylsilyloxy]-4-(3-hydroxypropoxy)-2-methylenecyclohexylidene]-1-chloroethane
342645-82-3

[3R-(1Z,3β,4α,5α)]-2-[3,5-bis[(1,1-dimethylethyl)dimethylsilyloxy]-4-(3-hydroxypropoxy)-2-methylenecyclohexylidene]-1-chloroethane

Eldecalcitol
104121-92-8

Eldecalcitol

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: 92 percent / imidazole / dimethylformamide / 0.25 h / 20 °C
2.1: n-BuLi / hexane; tetrahydrofuran / 0.33 h / -50 °C
3.1: 86 mg / aq. H2O2 / CHCl3 / 0.02 h
4.1: 66 percent / n-butyllithium / tetrahydrofuran; toluene / 0.5 h / -50 °C
5.1: Mg / tetrahydrofuran / 0.5 h / 20 °C
5.2: 89 percent / CuBr*Me2S / tetrahydrofuran / 0.5 h / -10 °C
6.1: 96 percent / HF/pyridine / tetrahydrofuran / 20 °C
View Scheme
[3R-(1Z,3β,4α,5α)]-2-[3,5-bis[(1,1-dimethylethyl)dimethylsilyloxy]-4-[2-(ethoxycarbonyl)ethoxy]-2-methylenecyclohexylidene]ethyl trimethylacetate
342645-81-2

[3R-(1Z,3β,4α,5α)]-2-[3,5-bis[(1,1-dimethylethyl)dimethylsilyloxy]-4-[2-(ethoxycarbonyl)ethoxy]-2-methylenecyclohexylidene]ethyl trimethylacetate

Eldecalcitol
104121-92-8

Eldecalcitol

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1.1: 91 percent / LiAlH4 / tetrahydrofuran / 0.25 h / 0 °C
2.1: 57 percent / NCS; Me2S / CH2Cl2 / 0.67 h
3.1: 92 percent / imidazole / dimethylformamide / 0.25 h / 20 °C
4.1: n-BuLi / hexane; tetrahydrofuran / 0.33 h / -50 °C
5.1: 86 mg / aq. H2O2 / CHCl3 / 0.02 h
6.1: 66 percent / n-butyllithium / tetrahydrofuran; toluene / 0.5 h / -50 °C
7.1: Mg / tetrahydrofuran / 0.5 h / 20 °C
7.2: 89 percent / CuBr*Me2S / tetrahydrofuran / 0.5 h / -10 °C
8.1: 96 percent / HF/pyridine / tetrahydrofuran / 20 °C
View Scheme
(S)-2-[(1R,3aR,7aR)-octahydro-7a-methyl-4-oxo-4H-inden-1-yl]propyl 4-methylbenzenesulfonate
342645-83-4

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

Eldecalcitol
104121-92-8

Eldecalcitol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: 66 percent / n-butyllithium / tetrahydrofuran; toluene / 0.5 h / -50 °C
2.1: Mg / tetrahydrofuran / 0.5 h / 20 °C
2.2: 89 percent / CuBr*Me2S / tetrahydrofuran / 0.5 h / -10 °C
3.1: 96 percent / HF/pyridine / tetrahydrofuran / 20 °C
View Scheme

Eldecalcitol Specification

The Eldecalcitol, with the CAS registry number 104121-92-8, is also known as 2-(3-Hydroxypropoxy)-1,25-dihydroxyvitamin D3. This chemical's molecular formula is C30H50O5 and molecular weight is 490.71. What's more, its systematic name is 4-(3-Chloropropyl)morpholin-4-ium chloride.

Physical properties of Eldecalcitol are: (1)ACD/LogP: 5.053; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): 5.05; (4)ACD/LogD (pH 7.4): 5.05; (5)ACD/BCF (pH 5.5): 4076.47; (6)ACD/BCF (pH 7.4): 4076.47; (7)ACD/KOC (pH 5.5): 13360.88; (8)ACD/KOC (pH 7.4): 13360.86; (9)#H bond acceptors: 5; (10)#H bond donors: 4; (11)#Freely Rotating Bonds: 14; (12)Polar Surface Area: 90.15 Å2; (13)Index of Refraction: 1.55; (14)Molar Refractivity: 141.502 cm3; (15)Molar Volume: 444.066 cm3; (16)Polarizability: 56.096×10-24cm3; (17)Surface Tension: 47.4 dyne/cm; (18)Density: 1.105 g/cm3; (19)Flash Point: 350.328 °C; (20)Enthalpy of Vaporization: 110.553 kJ/mol; (21)Boiling Point: 655.656 °C at 760 mmHg; (22)Vapour Pressure: 0 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES: O[C@H]1CC(\C(=C)[C@H](O)[C@H]1OCCCO)=C\C=C2/CCC[C@]3([C@H]2CC[C@@H]3[C@H](C)CCCC(O)(C)C)C
(2)Std. InChI: InChI=1S/C30H50O5/c1-20(9-6-15-29(3,4)34)24-13-14-25-22(10-7-16-30(24,25)5)11-12-23-19-26(32)28(27(33)21(23)2)35-18-8-17-31/h11-12,20,24-28,31-34H,2,6-10,13-19H2,1,3-5H3/b22-11+,23-12-/t20-,24-,25+,26+,27+,28+,30-/m1/s1
(3)Std. InChIKey: FZEXGDDBXLBRTD-SJSKTVLPSA-N  

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