1α-Hydroxy-25-oxo-27-norvitamin D₃

Base Information

• Chemical Name: 1α-Hydroxy-25-oxo-27-norvitamin D₃
• CAS No.: 77531-53-4
• Molecular Formula: C₂₆H₄₀O₃
• Molecular Weight: 400.602
• Mol file: 77531-53-4.mol

Synonyms:1α-Hydroxy-25-oxo-27-norvitamin D₃

Chemical Property of 1α-Hydroxy-25-oxo-27-norvitamin D₃

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1α-Hydroxy-25-oxo-27-norvitamin D₃

There total 16 articles about 1α-Hydroxy-25-oxo-27-norvitamin D₃ which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

(1R,5R)-2-Methyl-5-(1-methylethenyl)-2-cyclohexen-1-methanol (4895-08-3) → 1α-Hydroxy-25-oxo-27-norvitamin D3 (77531-53-4)

Guidance literature:

Multi-step reaction with 11 steps

1: 86 percent / tert-butylhydroperoxide, / vanadyl acetyl acetonate / benzene; toluene / 3 h / Ambient temperature

2: 88 percent / OsO₄, KIO₄ / tetrahydrofuran; H₂O / 15 h / Ambient temperature

3: 89 percent / m-CPBA / CHCl₃; H₂O / 25 h / pH 7.8

4: 1.) oxalyl chloride, Me₂SO 2.)Et₃N / 1.) CH₂Cl₂, 15 min, -60 deg C 2.) 0-10 deg C, 5 h

5: 95 percent / dimethylaminopyridine, pyridine / 6 h / 25 °C

6: 1.) zinc dust, Ph₃P 2.) pyridine / 1.) CH₂Cl₂, 15 min, r.t. 2.) CH₂Cl₂, 30 min r.t.

7: n-butyllithium / tetrahydrofuran; hexane / -78 to 20 deg C

9: 91 percent / Et₃N / bis-triphenylphosphine palladium dichloride / dimethylformamide / 1.5 h / 75 °C

10: 95 percent / H₂ / Lindlar's catalyst, quinoline / hexane / 0.75 h

11: 2.) AG 50W-X₄ resin / 1.) iso-octane, 4 h, reflux 2.) methanol, CH₂Cl₂, 24 h, r.t.

With pyridine; tert.-butylhydroperoxide; dmap; osmium(VIII) oxide; n-butyllithium; potassium metaperiodate; oxalyl dichloride; AG 50W-X₄ resin; hydrogen; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; zinc; quinoline; bis-triphenylphosphine-palladium(II) chloride; Lindlar's catalyst; bis(acetylacetonate)oxovanadium; In tetrahydrofuran; hexane; chloroform; water; N,N-dimethyl-formamide; toluene; benzene;

DOI:10.1016/S0040-4020(01)86410-3

Reference yield:

(1R,2S,4R,6S)-2-Hydroxymethyl-1-methyl-4-(1-methylethenyl)-7-oxybicyclo<4.1.0>heptane (113375-47-6) → 1α-Hydroxy-25-oxo-27-norvitamin D3 (77531-53-4)

Guidance literature:

Multi-step reaction with 10 steps

1: 88 percent / OsO₄, KIO₄ / tetrahydrofuran; H₂O / 15 h / Ambient temperature

2: 89 percent / m-CPBA / CHCl₃; H₂O / 25 h / pH 7.8

3: 1.) oxalyl chloride, Me₂SO 2.)Et₃N / 1.) CH₂Cl₂, 15 min, -60 deg C 2.) 0-10 deg C, 5 h

4: 95 percent / dimethylaminopyridine, pyridine / 6 h / 25 °C

5: 1.) zinc dust, Ph₃P 2.) pyridine / 1.) CH₂Cl₂, 15 min, r.t. 2.) CH₂Cl₂, 30 min r.t.

6: n-butyllithium / tetrahydrofuran; hexane / -78 to 20 deg C

8: 91 percent / Et₃N / bis-triphenylphosphine palladium dichloride / dimethylformamide / 1.5 h / 75 °C

9: 95 percent / H₂ / Lindlar's catalyst, quinoline / hexane / 0.75 h

10: 2.) AG 50W-X₄ resin / 1.) iso-octane, 4 h, reflux 2.) methanol, CH₂Cl₂, 24 h, r.t.

With pyridine; dmap; osmium(VIII) oxide; n-butyllithium; potassium metaperiodate; oxalyl dichloride; AG 50W-X₄ resin; hydrogen; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; zinc; quinoline; bis-triphenylphosphine-palladium(II) chloride; Lindlar's catalyst; In tetrahydrofuran; hexane; chloroform; water; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(01)86410-3

Reference yield:

(S)-p-mentha-6,8-dien-2-one (2244-16-8,6485-40-1) → 1α-Hydroxy-25-oxo-27-norvitamin D3 (77531-53-4)

Guidance literature:

Multi-step reaction with 12 steps

2: 86 percent / tert-butylhydroperoxide, / vanadyl acetyl acetonate / benzene; toluene / 3 h / Ambient temperature

3: 88 percent / OsO₄, KIO₄ / tetrahydrofuran; H₂O / 15 h / Ambient temperature

4: 89 percent / m-CPBA / CHCl₃; H₂O / 25 h / pH 7.8

5: 1.) oxalyl chloride, Me₂SO 2.)Et₃N / 1.) CH₂Cl₂, 15 min, -60 deg C 2.) 0-10 deg C, 5 h

6: 95 percent / dimethylaminopyridine, pyridine / 6 h / 25 °C

7: 1.) zinc dust, Ph₃P 2.) pyridine / 1.) CH₂Cl₂, 15 min, r.t. 2.) CH₂Cl₂, 30 min r.t.

8: n-butyllithium / tetrahydrofuran; hexane / -78 to 20 deg C

10: 91 percent / Et₃N / bis-triphenylphosphine palladium dichloride / dimethylformamide / 1.5 h / 75 °C

11: 95 percent / H₂ / Lindlar's catalyst, quinoline / hexane / 0.75 h

12: 2.) AG 50W-X₄ resin / 1.) iso-octane, 4 h, reflux 2.) methanol, CH₂Cl₂, 24 h, r.t.

With pyridine; tert.-butylhydroperoxide; dmap; osmium(VIII) oxide; n-butyllithium; potassium metaperiodate; oxalyl dichloride; AG 50W-X₄ resin; hydrogen; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; zinc; quinoline; bis-triphenylphosphine-palladium(II) chloride; Lindlar's catalyst; bis(acetylacetonate)oxovanadium; In tetrahydrofuran; hexane; chloroform; water; N,N-dimethyl-formamide; toluene; benzene;

DOI:10.1016/S0040-4020(01)86410-3

upstream raw materials:

1α-tert-Butyldimethylsilyloxy-25,25-(ethylenedioxy)-27-norprevitamin D₃ tert-butyldimethylsilyl ether

(S)-p-mentha-6,8-dien-2-one

(3S,5R)-3,5-Bis[(tert-butyldimethylsilyl)oxy]-2-methylcyclohex-1-en-1-carboxaldehyde

(1R,5R)-2-Methyl-5-(1-methylethenyl)-2-cyclohexen-1-methanol

Downstream raw materials:

calcitriol

Refernces