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

Base Information

• Chemical Name: 1α-tert-Butyldimethylsilyloxy-25,25-(ethylenedioxy)-27-norprevitamin D₃ tert-butyldimethylsilyl ether
• CAS No.: 134328-86-2
• Molecular Formula: C₄₀H₇₂O₄Si₂
• Molecular Weight: 673.18
• Mol file: 134328-86-2.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 16 articles about 1α-tert-Butyldimethylsilyloxy-25,25-(ethylenedioxy)-27-norprevitamin D₃ tert-butyldimethylsilyl ether 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: 95.0%

1α-tert-Butyldimethylsilyloxy-6,7-dehydro-25,25-(ethylenedioxy)-27-norprevitamin D3 tert-butyldimethylsilyl ether (116572-09-9) → 1α-tert-Butyldimethylsilyloxy-25,25-(ethylenedioxy)-27-norprevitamin D3 tert-butyldimethylsilyl ether (134328-86-2)

Guidance literature:

With hydrogen; quinoline; Lindlar's catalyst; In hexane; for 0.75h;

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

Reference yield:

(1R,5R)-2-Methyl-5-(1-methylethenyl)-2-cyclohexen-1-methanol (4895-08-3) → 1α-tert-Butyldimethylsilyloxy-25,25-(ethylenedioxy)-27-norprevitamin D3 tert-butyldimethylsilyl ether (134328-86-2)

Guidance literature:

Multi-step reaction with 10 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

With pyridine; tert.-butylhydroperoxide; dmap; osmium(VIII) oxide; n-butyllithium; potassium metaperiodate; oxalyl dichloride; 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-tert-Butyldimethylsilyloxy-25,25-(ethylenedioxy)-27-norprevitamin D3 tert-butyldimethylsilyl ether (134328-86-2)

Guidance literature:

Multi-step reaction with 9 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

With pyridine; dmap; osmium(VIII) oxide; n-butyllithium; potassium metaperiodate; oxalyl dichloride; 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

upstream raw materials:

1α-tert-Butyldimethylsilyloxy-6,7-dehydro-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:

1α-Hydroxy-25-oxo-27-norvitamin D₃

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

calcitriol

Refernces