Decanoic acid, 6-[(1R)-1-[[(1,1-dimethylethyl)dimethylsilyl]oxy]propyl]-2,3-dihydroxy-2,8- dimethyl-, phenylmethyl ester, (2S,3R,6R,8S)-

Base Information

• Chemical Name: Decanoic acid, 6-[(1R)-1-[[(1,1-dimethylethyl)dimethylsilyl]oxy]propyl]-2,3-dihydroxy-2,8- dimethyl-, phenylmethyl ester, (2S,3R,6R,8S)-
• CAS No.: 506449-81-6
• Molecular Formula: C28H50O5Si
• Molecular Weight: 494.788
• Mol file: 506449-81-6.mol

Synonyms:

Chemical Property of Decanoic acid, 6-[(1R)-1-[[(1,1-dimethylethyl)dimethylsilyl]oxy]propyl]-2,3-dihydroxy-2,8- dimethyl-, phenylmethyl ester, (2S,3R,6R,8S)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Decanoic acid, 6-[(1R)-1-[[(1,1-dimethylethyl)dimethylsilyl]oxy]propyl]-2,3-dihydroxy-2,8- dimethyl-, phenylmethyl ester, (2S,3R,6R,8S)-

There total 13 articles about Decanoic acid, 6-[(1R)-1-[[(1,1-dimethylethyl)dimethylsilyl]oxy]propyl]-2,3-dihydroxy-2,8- dimethyl-, phenylmethyl ester, (2S,3R,6R,8S)- 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:

(E)-2-penten-1-ol (1576-96-1) → (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)

Guidance literature:

Multi-step reaction with 12 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

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

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

Reference yield:

pent-2-yn-1-ol (6261-22-9) → (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)

Guidance literature:

Multi-step reaction with 13 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

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

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

Reference yield:

(2R,3R)-3-(ethyloxiran-2-yl)methanol (94424-88-1) → (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)

Guidance literature:

Multi-step reaction with 11 steps

1: 63 percent / CuCl / diethyl ether / 24 h / -78 °C

2: pyridine / 4 h / 0 °C

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

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

5: 99 percent / NaH / tetrahydrofuran / 17 h / -78 - 20 °C

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

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

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

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

With 1H-imidazole; lithium borohydride; methanesulfonamide; AD-mix-β; hydrogen; sodium hydride; diisobutylaluminium hydride; copper(l) chloride; palladium on activated charcoal; In tetrahydrofuran; pyridine; diethyl ether; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; tert-butyl alcohol; 5: Swern oxidation / 6: Horner-Emmons olefination / 9: Swern oxidation;

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

upstream raw materials:

(E)-(6R,8S)-6-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-propyl]-2,8-dimethyl-dec-2-enoic acid benzyl ester

(E)-2-penten-1-ol

pent-2-yn-1-ol

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

Downstream raw materials:

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