(2S,6R,8S)-6-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-propyl]-2-hydroxy-2,8-dimethyl-3-oxo-decanoic acid benzyl ester

Base Information

• Chemical Name: (2S,6R,8S)-6-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-propyl]-2-hydroxy-2,8-dimethyl-3-oxo-decanoic acid benzyl ester
• CAS No.: 506449-82-7
• Molecular Formula: C₂₈H₄₈O₅Si
• Molecular Weight: 492.772
• Mol file: 506449-82-7.mol

Synonyms:(2S,6R,8S)-6-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-propyl]-2-hydroxy-2,8-dimethyl-3-oxo-decanoic acid benzyl ester

Chemical Property of (2S,6R,8S)-6-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-propyl]-2-hydroxy-2,8-dimethyl-3-oxo-decanoic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,6R,8S)-6-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-propyl]-2-hydroxy-2,8-dimethyl-3-oxo-decanoic acid benzyl ester

There total 14 articles about (2S,6R,8S)-6-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-propyl]-2-hydroxy-2,8-dimethyl-3-oxo-decanoic acid benzyl ester 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: 83.0%

(2S,3R,6R,8S)-6-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-propyl]-2,3-dihydroxy-2,8-dimethyl-decanoic acid benzyl ester (506449-81-6) → (2S,6R,8S)-6-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-propyl]-2-hydroxy-2,8-dimethyl-3-oxo-decanoic acid benzyl ester (506449-82-7)

Guidance literature:

With pyridine-SO₃ complex; dimethyl sulfoxide; triethylamine; In dimethyl sulfoxide; at 10 - 20 ℃; for 24h;

DOI:10.1016/S0040-4039(02)02324-9

Reference yield:

(E)-2-penten-1-ol (1576-96-1) → (2S,6R,8S)-6-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-propyl]-2-hydroxy-2,8-dimethyl-3-oxo-decanoic acid benzyl ester (506449-82-7)

Guidance literature:

Multi-step reaction with 13 steps

1: 80 percent / TBHP; D-DIPT; Ti(OiPr)4 / CH₂Cl₂ / 10 h / -20 °C

2: 63 percent / CuCl / diethyl ether / 24 h / -78 °C

3: pyridine / 4 h / 0 °C

4: imidazole / dimethylformamide / 24 h / 0 - 20 °C

5: LiBH₄ / diethyl ether / 24 h / 0 - 20 °C

6: 99 percent / NaH / tetrahydrofuran / 17 h / -78 - 20 °C

7: H₂ / Pd/C / ethyl acetate / 36 h / 20 °C

8: DIBAL-H / CH₂Cl₂ / 6 h / -78 - 20 °C

9: NaH / tetrahydrofuran / 27 h / -78 - 20 °C

10: AD-mix-β; MeSO2NH2 / 2-methyl-propan-2-ol; H2O / 66 h / 0 °C

11: 83 percent / SO_3.Py; DMSO; Et₃N / dimethylsulfoxide / 24 h / 10 - 20 °C

With 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; lithium borohydride; pyridine-SO₃ complex; methanesulfonamide; AD-mix-β; hydrogen; sodium hydride; diisobutylaluminium hydride; D-(-)-diisopropyl tartrate; dimethyl sulfoxide; triethylamine; copper(l) chloride; palladium on activated charcoal; In tetrahydrofuran; pyridine; diethyl ether; dichloromethane; water; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide; tert-butyl alcohol; 1: Sharpless asymmetric epoxidation / 6: Swern oxidation / 7: Horner-Emmons olefination / 10: Swern oxidation / 13: Parikh-Doering oxidation;

DOI:10.1016/S0040-4039(02)02324-9

Reference yield:

pent-2-yn-1-ol (6261-22-9) → (2S,6R,8S)-6-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-propyl]-2-hydroxy-2,8-dimethyl-3-oxo-decanoic acid benzyl ester (506449-82-7)

Guidance literature:

Multi-step reaction with 14 steps

1: 81 percent / LiAlH₄ / diethyl ether / 3 h / 0 °C / Heating

2: 80 percent / TBHP; D-DIPT; Ti(OiPr)4 / CH₂Cl₂ / 10 h / -20 °C

3: 63 percent / CuCl / diethyl ether / 24 h / -78 °C

4: pyridine / 4 h / 0 °C

5: imidazole / dimethylformamide / 24 h / 0 - 20 °C

6: LiBH₄ / diethyl ether / 24 h / 0 - 20 °C

7: 99 percent / NaH / tetrahydrofuran / 17 h / -78 - 20 °C

8: H₂ / Pd/C / ethyl acetate / 36 h / 20 °C

9: DIBAL-H / CH₂Cl₂ / 6 h / -78 - 20 °C

10: NaH / tetrahydrofuran / 27 h / -78 - 20 °C

11: AD-mix-β; MeSO2NH2 / 2-methyl-propan-2-ol; H2O / 66 h / 0 °C

12: 83 percent / SO_3.Py; DMSO; Et₃N / dimethylsulfoxide / 24 h / 10 - 20 °C

With 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; lithium aluminium tetrahydride; lithium borohydride; pyridine-SO₃ complex; methanesulfonamide; AD-mix-β; hydrogen; sodium hydride; diisobutylaluminium hydride; D-(-)-diisopropyl tartrate; dimethyl sulfoxide; triethylamine; copper(l) chloride; palladium on activated charcoal; In tetrahydrofuran; pyridine; diethyl ether; dichloromethane; water; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide; tert-butyl alcohol; 2: Sharpless asymmetric epoxidation / 7: Swern oxidation / 8: Horner-Emmons olefination / 11: Swern oxidation / 14: Parikh-Doering oxidation;

DOI:10.1016/S0040-4039(02)02324-9

upstream raw materials:

(2S,3R,6R,8S)-6-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-propyl]-2,3-dihydroxy-2,8-dimethyl-decanoic acid benzyl ester

(E)-2-penten-1-ol

pent-2-yn-1-ol

(2R,3R)-3-(ethyloxiran-2-yl)methanol