1α-[(tert-butyldimethylsilyl)oxy]-25-[(methoxymethyl)oxy]previtamin D₂ tert-butyldimethylsilyl ether

Base Information

• Chemical Name: 1α-[(tert-butyldimethylsilyl)oxy]-25-[(methoxymethyl)oxy]previtamin D₂ tert-butyldimethylsilyl ether
• CAS No.: 145354-39-8
• Molecular Formula: C₄₂H₇₆O₄Si₂
• Molecular Weight: 701.234
• Mol file: 145354-39-8.mol

Synonyms:1α-[(tert-butyldimethylsilyl)oxy]-25-[(methoxymethyl)oxy]previtamin D₂ tert-butyldimethylsilyl ether

Chemical Property of 1α-[(tert-butyldimethylsilyl)oxy]-25-[(methoxymethyl)oxy]previtamin D₂ tert-butyldimethylsilyl ether

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1α-[(tert-butyldimethylsilyl)oxy]-25-[(methoxymethyl)oxy]previtamin D₂ tert-butyldimethylsilyl ether

There total 18 articles about 1α-[(tert-butyldimethylsilyl)oxy]-25-[(methoxymethyl)oxy]previtamin D₂ 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:

Benzoic acid (1R,3aR,4S,7aR)-7a-methyl-1-((S)-1-methyl-2-oxo-ethyl)-octahydro-inden-4-yl ester (66774-71-8) → 1α-[(tert-butyldimethylsilyl)oxy]-25-[(methoxymethyl)oxy]previtamin D2 tert-butyldimethylsilyl ether (145354-39-8)

Guidance literature:

Multi-step reaction with 9 steps

1: 1) 2,6-di-tert-butylpyridine, 2a) TMSTf, 2b) Et₃N, MeOH / 1) CH₂Cl₂, -78 deg C, 5 min, 2a) -78 deg C, 2 h, 2b) -78 deg C, 5 min then to RT

2: TiCl₄ / CH₂Cl₂ / 12 h / -78 °C

3: 92 percent / DMAP, i-Pr₂NEt / CH₂Cl₂ / 18 h / 0 °C

4: 91 percent / LDA / tetrahydrofuran / 0.5 h / -78 °C

6: 1) LDA / 1) -78 deg C

7: 94 percent / Et₃N / (Ph₃P)2PdCl₂ / 75 °C

8: H₂, Lindlar catalyst, quinoline / hexane

9: 2,2,4-trimethyl-pentane / Heating

With quinoline; methanol; dmap; Lindlar's catalyst; 2,6-di-tert-butyl-pyridine; TMSTf; hydrogen; titanium tetrachloride; triethylamine; N-ethyl-N,N-diisopropylamine; lithium diisopropyl amide; bis-triphenylphosphine-palladium(II) chloride; In tetrahydrofuran; 2,2,4-trimethylpentane; hexane; dichloromethane;

DOI:10.1021/jo00053a024

Reference yield:

(24R,22E)-des-A,B-8β-(benzoyloxy)ergost-22-ene (68702-86-3) → 1α-[(tert-butyldimethylsilyl)oxy]-25-[(methoxymethyl)oxy]previtamin D2 tert-butyldimethylsilyl ether (145354-39-8)

Guidance literature:

Multi-step reaction with 10 steps

1: 95 percent / pyridine, ozone / methanol; CH₂Cl₂ / 0.42 h / -78 °C

2: 1) 2,6-di-tert-butylpyridine, 2a) TMSTf, 2b) Et₃N, MeOH / 1) CH₂Cl₂, -78 deg C, 5 min, 2a) -78 deg C, 2 h, 2b) -78 deg C, 5 min then to RT

3: TiCl₄ / CH₂Cl₂ / 12 h / -78 °C

4: 92 percent / DMAP, i-Pr₂NEt / CH₂Cl₂ / 18 h / 0 °C

5: 91 percent / LDA / tetrahydrofuran / 0.5 h / -78 °C

7: 1) LDA / 1) -78 deg C

8: 94 percent / Et₃N / (Ph₃P)2PdCl₂ / 75 °C

9: H₂, Lindlar catalyst, quinoline / hexane

10: 2,2,4-trimethyl-pentane / Heating

With pyridine; quinoline; methanol; dmap; Lindlar's catalyst; 2,6-di-tert-butyl-pyridine; TMSTf; hydrogen; titanium tetrachloride; ozone; triethylamine; N-ethyl-N,N-diisopropylamine; lithium diisopropyl amide; bis-triphenylphosphine-palladium(II) chloride; In tetrahydrofuran; methanol; 2,2,4-trimethylpentane; hexane; dichloromethane;

DOI:10.1021/jo00053a024

Reference yield:

(1R,3aR,4S,7aR)-7a-methyl-1-<(2E)-(1R,4R)-1,4,5-trimethyl-hex-2-enyl>-octahydro-1H-inden-4-ol (55812-82-3,63730-57-4,63730-58-5,102281-42-5) → 1α-[(tert-butyldimethylsilyl)oxy]-25-[(methoxymethyl)oxy]previtamin D2 tert-butyldimethylsilyl ether (145354-39-8)

Guidance literature:

Multi-step reaction with 11 steps

1: 95 percent / DMAP, pyridine / 14 h / refrigerator

2: 95 percent / pyridine, ozone / methanol; CH₂Cl₂ / 0.42 h / -78 °C

3: 1) 2,6-di-tert-butylpyridine, 2a) TMSTf, 2b) Et₃N, MeOH / 1) CH₂Cl₂, -78 deg C, 5 min, 2a) -78 deg C, 2 h, 2b) -78 deg C, 5 min then to RT

4: TiCl₄ / CH₂Cl₂ / 12 h / -78 °C

5: 92 percent / DMAP, i-Pr₂NEt / CH₂Cl₂ / 18 h / 0 °C

6: 91 percent / LDA / tetrahydrofuran / 0.5 h / -78 °C

8: 1) LDA / 1) -78 deg C

9: 94 percent / Et₃N / (Ph₃P)2PdCl₂ / 75 °C

10: H₂, Lindlar catalyst, quinoline / hexane

11: 2,2,4-trimethyl-pentane / Heating

With pyridine; quinoline; methanol; dmap; Lindlar's catalyst; 2,6-di-tert-butyl-pyridine; TMSTf; hydrogen; titanium tetrachloride; ozone; triethylamine; N-ethyl-N,N-diisopropylamine; lithium diisopropyl amide; bis-triphenylphosphine-palladium(II) chloride; In tetrahydrofuran; methanol; 2,2,4-trimethylpentane; hexane; dichloromethane;

DOI:10.1021/jo00053a024

upstream raw materials:

(S)-2-[(1R,3aR,4S,7aR)-octahydro-4-[(1,1-dimethylethyl)dimethylsilyloxy]-7a-methyl-1H-inden-1-yl]propanal

Phosphoric acid diethyl ester (E)-(S)-1-[(S)-1-((1R,3aR,4S,7aR)-4-hydroxy-7a-methyl-octahydro-inden-1-yl)-ethyl]-4-methoxymethoxy-4-methyl-pent-2-enyl ester

Phosphoric acid diethyl ester (E)-(S)-4-methoxymethoxy-4-methyl-1-[(S)-1-((1R,3aR,7aR)-7a-methyl-4-oxo-octahydro-inden-1-yl)-ethyl]-pent-2-enyl ester

Phosphoric acid (E)-(S)-1-{(S)-1-[(1R,3aR,4S,7aR)-4-(tert-butyl-dimethyl-silanyloxy)-7a-methyl-octahydro-inden-1-yl]-ethyl}-4-methoxymethoxy-4-methyl-pent-2-enyl ester diethyl ester

Downstream raw materials:

ercalcitriol

Refernces

• 1、 Granja,Castedo,Mourino. "Studies on the opening of dioxanone and acetal templates and application to the synthesis of 1α,25-dihydroxyvitamin D2". . p. 124 - 131. Retrieved 2007/10/02.