4(R),5(S)-bis[(tert-butyldimethylsilyl)oxy]-N-[1(S)-(cyclohexylmethyl)-2(R),3(S)-dihydroxy-5-methylhexyl]-2(R)-(cyclopropylmethyl)-6-phenylhexanamide

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Chemical Name:4(R),5(S)-bis[(tert-butyldimethylsilyl)oxy]-N-[1(S)-(cyclohexylmethyl)-2(R),3(S)-dihydroxy-5-methylhexyl]-2(R)-(cyclopropylmethyl)-6-phenylhexanamide
CAS No.:155417-41-7
Molecular Formula:C₄₂H₇₇NO₅Si₂
Molecular Weight:732.248
Hs Code.:

Synonyms:4(R),5(S)-bis[(tert-butyldimethylsilyl)oxy]-N-[1(S)-(cyclohexylmethyl)-2(R),3(S)-dihydroxy-5-methylhexyl]-2(R)-(cyclopropylmethyl)-6-phenylhexanamide

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Chemical Property of 4(R),5(S)-bis[(tert-butyldimethylsilyl)oxy]-N-[1(S)-(cyclohexylmethyl)-2(R),3(S)-dihydroxy-5-methylhexyl]-2(R)-(cyclopropylmethyl)-6-phenylhexanamide

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Technology Process of 4(R),5(S)-bis[(tert-butyldimethylsilyl)oxy]-N-[1(S)-(cyclohexylmethyl)-2(R),3(S)-dihydroxy-5-methylhexyl]-2(R)-(cyclopropylmethyl)-6-phenylhexanamide

There total 10 articles about 4(R),5(S)-bis[(tert-butyldimethylsilyl)oxy]-N-[1(S)-(cyclohexylmethyl)-2(R),3(S)-dihydroxy-5-methylhexyl]-2(R)-(cyclopropylmethyl)-6-phenylhexanamide 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: 67.0%

: 122621-77-6
(2S,3R,4S)-2-amino-1-cyclohexyl-3,4-dihydroxy-6-methylheptane

: 220589-04-8
(2R,4R,5S)-4,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-cyclopropylmethyl-6-phenyl-hexanoic acid

: 155417-41-7
4(R),5(S)-bis[(tert-butyldimethylsilyl)oxy]-N-[1(S)-(cyclohexylmethyl)-2(R),3(S)-dihydroxy-5-methylhexyl]-2(R)-(cyclopropylmethyl)-6-phenylhexanamide

Guidance literature:: With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20 ℃; for 1h;
DOI:10.1016/S0968-0896(98)80011-4

Reference yield:

: 6052-66-0,112370-40-8,123877-73-6
1-phenyl-3-buten-2-ol

: 155417-41-7
4(R),5(S)-bis[(tert-butyldimethylsilyl)oxy]-N-[1(S)-(cyclohexylmethyl)-2(R),3(S)-dihydroxy-5-methylhexyl]-2(R)-(cyclopropylmethyl)-6-phenylhexanamide

Guidance literature:: Multi-step reaction with 8 steps

1.1: 1,5-hexadiene; SOBr₂ / 1,2-dichloro-ethane / 1.5 h / 0 °C

2.1: n-BuLi; i-Pr₂NH / hexane; tetrahydrofuran / 1 h / -78 °C

2.2: 56 percent / DMPU / hexane; tetrahydrofuran / 2.75 h / -78 - 0 °C

3.1: 92 percent / H₂O₂; LiOH*H₂O / tetrahydrofuran; H₂O / 19 h / 0 - 25 °C

4.1: 80 percent / MCPBA / CH₂Cl₂ / 15.25 h / 0 - 25 °C

5.1: 44 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 - 25 °C

6.1: LiOH*H₂O / tetrahydrofuran; H₂O / 25 °C

6.2: 2,6-lutidine / CH₂Cl₂; dimethylformamide / 0 - 25 °C

7.1: K₂CO₃ / methanol; tetrahydrofuran; H₂O / 20 °C

8.1: 67 percent / i-Pr₂NEt; BOP*PF₆ / dimethylformamide / 1 h / 20 °C

With 2,6-dimethylpyridine; lithium hydroxide; sulfurous dibromide; n-butyllithium; 1,5-Hexadien; dihydrogen peroxide; potassium carbonate; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; diisopropylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; methanol; hexane; dichloromethane; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide; 1.1: Substitution / 2.1: Metallation / 2.2: Alkylation / 3.1: Hydrolysis / 4.1: Oxidation / 5.1: silylation / 6.1: Hydrolysis / 6.2: silylation / 7.1: Hydrolysis / 8.1: Acylation;
DOI:10.1016/S0968-0896(98)80011-4

Reference yield:

: 40734-75-6
(E)-(4-bromobut-2-en-1-yl)benzene

: 155417-41-7
4(R),5(S)-bis[(tert-butyldimethylsilyl)oxy]-N-[1(S)-(cyclohexylmethyl)-2(R),3(S)-dihydroxy-5-methylhexyl]-2(R)-(cyclopropylmethyl)-6-phenylhexanamide

Guidance literature:: Multi-step reaction with 7 steps

1.1: n-BuLi; i-Pr₂NH / hexane; tetrahydrofuran / 1 h / -78 °C

1.2: 56 percent / DMPU / hexane; tetrahydrofuran / 2.75 h / -78 - 0 °C

2.1: 92 percent / H₂O₂; LiOH*H₂O / tetrahydrofuran; H₂O / 19 h / 0 - 25 °C

3.1: 80 percent / MCPBA / CH₂Cl₂ / 15.25 h / 0 - 25 °C

4.1: 44 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 - 25 °C

5.1: LiOH*H₂O / tetrahydrofuran; H₂O / 25 °C

5.2: 2,6-lutidine / CH₂Cl₂; dimethylformamide / 0 - 25 °C

6.1: K₂CO₃ / methanol; tetrahydrofuran; H₂O / 20 °C

7.1: 67 percent / i-Pr₂NEt; BOP*PF₆ / dimethylformamide / 1 h / 20 °C

With 2,6-dimethylpyridine; lithium hydroxide; n-butyllithium; dihydrogen peroxide; potassium carbonate; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; diisopropylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; methanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; 1.1: Metallation / 1.2: Alkylation / 2.1: Hydrolysis / 3.1: Oxidation / 4.1: silylation / 5.1: Hydrolysis / 5.2: silylation / 6.1: Hydrolysis / 7.1: Acylation;
DOI:10.1016/S0968-0896(98)80011-4