(R)-6-[(1E,7Z)-(3R,4R,6R)-8-(Benzyl-dimethyl-silanyl)-6-(tert-butyl-dimethyl-silanyloxy)-4-hydroxy-3-methyl-3-triethylsilanyloxy-octa-1,7-dienyl]-5,6-dihydro-pyran-2-one

Base Information

• Chemical Name: (R)-6-[(1E,7Z)-(3R,4R,6R)-8-(Benzyl-dimethyl-silanyl)-6-(tert-butyl-dimethyl-silanyloxy)-4-hydroxy-3-methyl-3-triethylsilanyloxy-octa-1,7-dienyl]-5,6-dihydro-pyran-2-one
• CAS No.: 850146-96-2
• Molecular Formula: C₃₅H₆₀O₅Si₃
• Molecular Weight: 645.115
• Mol file: 850146-96-2.mol

Synonyms:(R)-6-[(1E,7Z)-(3R,4R,6R)-8-(Benzyl-dimethyl-silanyl)-6-(tert-butyl-dimethyl-silanyloxy)-4-hydroxy-3-methyl-3-triethylsilanyloxy-octa-1,7-dienyl]-5,6-dihydro-pyran-2-one

Chemical Property of (R)-6-[(1E,7Z)-(3R,4R,6R)-8-(Benzyl-dimethyl-silanyl)-6-(tert-butyl-dimethyl-silanyloxy)-4-hydroxy-3-methyl-3-triethylsilanyloxy-octa-1,7-dienyl]-5,6-dihydro-pyran-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-6-[(1E,7Z)-(3R,4R,6R)-8-(Benzyl-dimethyl-silanyl)-6-(tert-butyl-dimethyl-silanyloxy)-4-hydroxy-3-methyl-3-triethylsilanyloxy-octa-1,7-dienyl]-5,6-dihydro-pyran-2-one

There total 16 articles about (R)-6-[(1E,7Z)-(3R,4R,6R)-8-(Benzyl-dimethyl-silanyl)-6-(tert-butyl-dimethyl-silanyloxy)-4-hydroxy-3-methyl-3-triethylsilanyloxy-octa-1,7-dienyl]-5,6-dihydro-pyran-2-one 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: 53.0%

(R)-6-((E,3R,4R,5R)-8-(benzyldimethylsilyl)-3-trimethylsiloxy-4-hydroxy-6-tert-butyldimethylsiloxybut-3-methyloct-1-en-7-ynyl)-5,6-dihydropyran-2-one (850146-95-1) → (R)-6-[(E)-(3R,4R,6R)-8-(Benzyl-dimethyl-silanyl)-6-(tert-butyl-dimethyl-silanyloxy)-4-hydroxy-3-methyl-3-triethylsilanyloxy-oct-1-enyl]-5,6-dihydro-pyran-2-one + (R)-6-[(1E,7Z)-(3R,4R,6R)-8-(Benzyl-dimethyl-silanyl)-6-(tert-butyl-dimethyl-silanyloxy)-4-hydroxy-3-methyl-3-triethylsilanyloxy-octa-1,7-dienyl]-5,6-dihydro-pyran-2-one (850146-96-2)

Guidance literature:

With trisylhydrazine; sodium hydrogencarbonate; In methanol; at 20 ℃; for 12h;

DOI:10.1021/ja042435i

Reference yield:

4-(benzyldimethylsilyl)but-3-yn-2-one (850146-87-1) → (R)-6-[(1E,7Z)-(3R,4R,6R)-8-(Benzyl-dimethyl-silanyl)-6-(tert-butyl-dimethyl-silanyloxy)-4-hydroxy-3-methyl-3-triethylsilanyloxy-octa-1,7-dienyl]-5,6-dihydro-pyran-2-one (850146-96-2)

Guidance literature:

Multi-step reaction with 12 steps

1.1: 58 percent / (S,S)-2,6{[2-(Ph₂(OH)C)pyrrolidin-1-yl]CH₂}2-4MePhOH; Et₂Zn; molecular sieves 4 Angstroem / tetrahydrofuran; hexane / 21 h / 20 °C

2.1: 88 percent / chiral Ru catalyst / propan-2-ol / 17.5 h / 20 °C

3.1: imidazole / dimethylformamide / 21 h / 20 °C

4.1: 8.52 g / CSA / acetone / 0.67 h / 20 °C

5.1: 97 percent / i-Pr₂NEt; n-Bu₄I / dimethylformamide / 22 h / 40 °C

6.1: allylmagnesium bromide / tetrahydrofuran / 0.33 h / 20 °C

6.2: 75 percent / isopropylmagnesium chloride; s-BuLi / tetrahydrofuran; cyclohexane / 3 h / -78 °C

7.1: 91 percent / aq. HF / acetonitrile; methanol / 4 h / 0 °C

8.1: 99 percent / Pr₂NEt / CH₂Cl₂ / 2 h / 0 °C

9.1: 99 percent / i-Pr₂NEt / CH₂Cl₂ / 0.25 h / 0 °C

10.1: 93 percent / first generation Grubbs catalyst / CH₂Cl₂ / 18 h / Heating

11.1: 94 percent / DDQ; water / CH₂Cl₂ / 4 h / 20 °C

12.1: 53 percent / 2,4,6-tri(iPr)C₆H₂SO₂NHNH₂; NaHCO₃ / methanol / 12 h / 20 °C

With 1H-imidazole; Grubbs catalyst first generation; dipropylethylamine; 4 A molecular sieve; chiral Ru catalyst; trisylhydrazine; camphor-10-sulfonic acid; hydrogen fluoride; water; diethylzinc; sodium hydrogencarbonate; N-ethyl-N,N-diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; ((2S,2'S)-((2-hydroxy-5-methyl-1,3-phenylene)bis(methylene))bis(pyrrolidine-1,2-diyl))bis(diphenylmethanol); allylmagnesium bromide; In tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide; isopropyl alcohol; acetone; acetonitrile;

DOI:10.1021/ja042435i

Reference yield:

(R)-1-(Benzyl-dimethyl-silanyl)-6,6-diethoxy-5-hydroxy-hept-1-yn-3-one (850146-88-2) → (R)-6-[(1E,7Z)-(3R,4R,6R)-8-(Benzyl-dimethyl-silanyl)-6-(tert-butyl-dimethyl-silanyloxy)-4-hydroxy-3-methyl-3-triethylsilanyloxy-octa-1,7-dienyl]-5,6-dihydro-pyran-2-one (850146-96-2)

Guidance literature:

Multi-step reaction with 11 steps

1.1: 88 percent / chiral Ru catalyst / propan-2-ol / 17.5 h / 20 °C

2.1: imidazole / dimethylformamide / 21 h / 20 °C

3.1: 8.52 g / CSA / acetone / 0.67 h / 20 °C

4.1: 97 percent / i-Pr₂NEt; n-Bu₄I / dimethylformamide / 22 h / 40 °C

5.1: allylmagnesium bromide / tetrahydrofuran / 0.33 h / 20 °C

5.2: 75 percent / isopropylmagnesium chloride; s-BuLi / tetrahydrofuran; cyclohexane / 3 h / -78 °C

6.1: 91 percent / aq. HF / acetonitrile; methanol / 4 h / 0 °C

7.1: 99 percent / Pr₂NEt / CH₂Cl₂ / 2 h / 0 °C

8.1: 99 percent / i-Pr₂NEt / CH₂Cl₂ / 0.25 h / 0 °C

9.1: 93 percent / first generation Grubbs catalyst / CH₂Cl₂ / 18 h / Heating

10.1: 94 percent / DDQ; water / CH₂Cl₂ / 4 h / 20 °C

11.1: 53 percent / 2,4,6-tri(iPr)C₆H₂SO₂NHNH₂; NaHCO₃ / methanol / 12 h / 20 °C

With 1H-imidazole; Grubbs catalyst first generation; dipropylethylamine; chiral Ru catalyst; trisylhydrazine; camphor-10-sulfonic acid; hydrogen fluoride; water; sodium hydrogencarbonate; N-ethyl-N,N-diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; allylmagnesium bromide; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; isopropyl alcohol; acetone; acetonitrile;

DOI:10.1021/ja042435i

upstream raw materials:

(R)-6-((E,3R,4R,5R)-8-(benzyldimethylsilyl)-3-trimethylsiloxy-4-hydroxy-6-tert-butyldimethylsiloxybut-3-methyloct-1-en-7-ynyl)-5,6-dihydropyran-2-one

4-(benzyldimethylsilyl)but-3-yn-2-one

(R)-1-(Benzyl-dimethyl-silanyl)-6,6-diethoxy-5-hydroxy-hept-1-yn-3-one

(3R,5R)-1-(Benzyl-dimethyl-silanyl)-6,6-diethoxy-hept-1-yne-3,5-diol

Downstream raw materials:

dephosphofostriecin B