(2S,3R,4S)-4-Benzyloxy-2-methyl-1-triisopropylsilanyloxy-hept-6-en-3-ol

Base Information

• Chemical Name: (2S,3R,4S)-4-Benzyloxy-2-methyl-1-triisopropylsilanyloxy-hept-6-en-3-ol
• CAS No.: 865540-24-5
• Molecular Formula: C₂₄H₄₂O₃Si
• Molecular Weight: 406.681
• Mol file: 865540-24-5.mol

Synonyms:(2S,3R,4S)-4-Benzyloxy-2-methyl-1-triisopropylsilanyloxy-hept-6-en-3-ol

Chemical Property of (2S,3R,4S)-4-Benzyloxy-2-methyl-1-triisopropylsilanyloxy-hept-6-en-3-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R,4S)-4-Benzyloxy-2-methyl-1-triisopropylsilanyloxy-hept-6-en-3-ol

There total 4 articles about (2S,3R,4S)-4-Benzyloxy-2-methyl-1-triisopropylsilanyloxy-hept-6-en-3-ol 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: 96.0%

(2S,3R,4S)-4-Benzyloxy-2-methyl-hept-6-ene-1,3-diol (865540-44-9) + triisopropylsilyl chloride (13154-24-0) → (2S,3R,4S)-4-Benzyloxy-2-methyl-1-triisopropylsilanyloxy-hept-6-en-3-ol (865540-24-5)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 70 ℃; for 20h;

DOI:10.1021/ol051543m

Reference yield:

(2R,3R,4S)-4-Benzyloxy-1-((R)-4-benzyl-2-thioxo-oxazolidin-3-yl)-3-hydroxy-2-methyl-hept-6-en-1-one (865540-23-4) → (2S,3R,4S)-4-Benzyloxy-2-methyl-1-triisopropylsilanyloxy-hept-6-en-3-ol (865540-24-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 91 percent / lithium borohydride / methanol; diethyl ether; tetrahydrofuran / 1 h / 0 °C

2: 96 percent / imidazole / dimethylformamide / 20 h / 70 °C

With 1H-imidazole; lithium borohydride; In tetrahydrofuran; methanol; diethyl ether; N,N-dimethyl-formamide;

DOI:10.1021/ol051543m

Reference yield:

(S)-(-)-2-Benzyloxypent-4-enal (87604-58-8) → (2S,3R,4S)-4-Benzyloxy-2-methyl-1-triisopropylsilanyloxy-hept-6-en-3-ol (865540-24-5)

Guidance literature:

Multi-step reaction with 3 steps

1.1: TiCl₄; (-)-sparteine / CH₂Cl₂ / 0.33 h / 0 °C

1.2: 92 percent / N-methylpyrrolidinone / CH₂Cl₂ / -78 - 0 °C

2.1: 91 percent / lithium borohydride / methanol; diethyl ether; tetrahydrofuran / 1 h / 0 °C

3.1: 96 percent / imidazole / dimethylformamide / 20 h / 70 °C

With 1H-imidazole; lithium borohydride; titanium tetrachloride; (-)-sparteine; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ol051543m

upstream raw materials:

(2S,3R,4S)-4-Benzyloxy-2-methyl-hept-6-ene-1,3-diol

triisopropylsilyl chloride

(2R,3R,4S)-4-Benzyloxy-1-((R)-4-benzyl-2-thioxo-oxazolidin-3-yl)-3-hydroxy-2-methyl-hept-6-en-1-one

(S)-(-)-2-Benzyloxypent-4-enal

Downstream raw materials:

1-[3-hydroxy-7-(4-methoxy-benzyloxy)-3,5-dimethyl-8-triisopropylsilanyloxymethyl-oxocan-2-yl]-7-(4-methoxy-benzyloxy)-6-[2-(4-methoxy-benzyloxy)-1-(4-methoxy-benzyloxymethyl)-pent-4-enyloxy]-5-methyl-deca-1,9-dien-3-one

C₆₈H₉₈O₁₂Si

{(4S,5R,6S)-6-(4-Methoxy-benzyloxy)-5-[(1S,2R)-2-(4-methoxy-benzyloxy)-1-(4-methoxy-benzyloxymethyl)-pent-4-enyloxy]-4-methyl-2-oxo-non-8-enyl}-phosphonic acid dimethyl ester

(3S,4R,5S)-5-(4-Methoxy-benzyloxy)-4-[(1S,2R)-2-(4-methoxy-benzyloxy)-1-(4-methoxy-benzyloxymethyl)-pent-4-enyloxy]-3-methyl-oct-7-enoic acid methyl ester