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

Base Information

• Chemical Name: 4(S),5(S)-bis[(tert-butyldimethylsilyl)oxy]-N-[1(S)-(cyclohexylmethyl)-2(R),3(S)-dihydroxy-5-methylhexyl]-6-phenyl-2(S)-(2-thienylmethyl)hexanamide
• CAS No.: 220588-85-2
• Molecular Formula: C₄₃H₇₅NO₅SSi₂
• Molecular Weight: 774.309
• Mol file: 220588-85-2.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 14 articles about 4(S),5(S)-bis[(tert-butyldimethylsilyl)oxy]-N-[1(S)-(cyclohexylmethyl)-2(R),3(S)-dihydroxy-5-methylhexyl]-6-phenyl-2(S)-(2-thienylmethyl)hexanamide 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:

L-3-phenyllactic acid (20312-36-1) → 4(S),5(S)-bis[(tert-butyldimethylsilyl)oxy]-N-[1(S)-(cyclohexylmethyl)-2(R),3(S)-dihydroxy-5-methylhexyl]-6-phenyl-2(S)-(2-thienylmethyl)hexanamide (220588-85-2)

Guidance literature:

Multi-step reaction with 13 steps

1.1: NaH / tetrahydrofuran / 168 h

2.1: 16.3 g / LiAlH₄ / tetrahydrofuran / 60 h

3.1: dimethyl sulfoxide; oxalyl chloride; Et₃N / CH₂Cl₂ / 0.83 h / -78 °C

4.1: 4.82 g / diethyl ether / 1.25 h / -78 °C

5.1: O₃ / methanol / -78 °C

5.2: Me₂S / methanol / 4 h / -78 - 25 °C

6.1: 390 mg / Jones' reagent / acetone / 0.25 h / 0 - 20 °C

7.1: 84 percent / H₂ / Pd(OH)2/C / ethanol / 48 h

8.1: 87 percent / 2,6-lutidine / CH₂Cl₂ / 0.75 h / 0 - 25 °C

9.1: LDA / tetrahydrofuran; hexane / 0.5 h / -78 °C

9.2: 44 percent / HMPA / tetrahydrofuran; hexane / 3 h / -78 - -50 °C

10.1: aq. NaOH / tetrahydrofuran; methanol / 3.2 h / 0 °C

11.1: 2,6-lutidine / dimethylformamide / 15 h / 0 - 25 °C

12.1: 649 mg / K₂CO₃ / methanol; tetrahydrofuran; H₂O / 2.5 h / 25 °C

13.1: 582 mg / i-Pr₂NEt; BOP*PF₆ / CH₂Cl₂ / 3 h / 20 °C

With 2,6-dimethylpyridine; sodium hydroxide; lithium aluminium tetrahydride; jones' reagent; oxalyl dichloride; hydrogen; sodium hydride; potassium carbonate; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; ozone; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; lithium diisopropyl amide; palladium dihydroxide; In tetrahydrofuran; methanol; diethyl ether; ethanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetone; 1.1: Alkylation / 2.1: Reduction / 3.1: Swern oxidation / 4.1: Grignard reaction / 5.1: ozonation / 5.2: Reduction / 6.1: Oxidation / 7.1: Hydrogenolysis / 8.1: silylation / 9.1: Metallation / 9.2: Alkylation / 10.1: Hydrolysis / 11.1: silylation / 12.1: Hydrolysis / 13.1: Acylation;

DOI:10.1016/S0968-0896(98)80011-4

Reference yield:

(2S)-2-benzyloxy-3-phenylpropanal (118535-75-4) → 4(S),5(S)-bis[(tert-butyldimethylsilyl)oxy]-N-[1(S)-(cyclohexylmethyl)-2(R),3(S)-dihydroxy-5-methylhexyl]-6-phenyl-2(S)-(2-thienylmethyl)hexanamide (220588-85-2)

Guidance literature:

Multi-step reaction with 10 steps

1.1: 4.82 g / diethyl ether / 1.25 h / -78 °C

2.1: O₃ / methanol / -78 °C

2.2: Me₂S / methanol / 4 h / -78 - 25 °C

3.1: 390 mg / Jones' reagent / acetone / 0.25 h / 0 - 20 °C

4.1: 84 percent / H₂ / Pd(OH)2/C / ethanol / 48 h

5.1: 87 percent / 2,6-lutidine / CH₂Cl₂ / 0.75 h / 0 - 25 °C

6.1: LDA / tetrahydrofuran; hexane / 0.5 h / -78 °C

6.2: 44 percent / HMPA / tetrahydrofuran; hexane / 3 h / -78 - -50 °C

7.1: aq. NaOH / tetrahydrofuran; methanol / 3.2 h / 0 °C

8.1: 2,6-lutidine / dimethylformamide / 15 h / 0 - 25 °C

9.1: 649 mg / K₂CO₃ / methanol; tetrahydrofuran; H₂O / 2.5 h / 25 °C

10.1: 582 mg / i-Pr₂NEt; BOP*PF₆ / CH₂Cl₂ / 3 h / 20 °C

With 2,6-dimethylpyridine; sodium hydroxide; jones' reagent; hydrogen; potassium carbonate; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; ozone; N-ethyl-N,N-diisopropylamine; lithium diisopropyl amide; palladium dihydroxide; In tetrahydrofuran; methanol; diethyl ether; ethanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetone; 1.1: Grignard reaction / 2.1: ozonation / 2.2: Reduction / 3.1: Oxidation / 4.1: Hydrogenolysis / 5.1: silylation / 6.1: Metallation / 6.2: Alkylation / 7.1: Hydrolysis / 8.1: silylation / 9.1: Hydrolysis / 10.1: Acylation;

DOI:10.1016/S0968-0896(98)80011-4

Reference yield:

(S)-2-(benzyloxy)-1-hydroxy-3-phenylpropane (123394-79-6) → 4(S),5(S)-bis[(tert-butyldimethylsilyl)oxy]-N-[1(S)-(cyclohexylmethyl)-2(R),3(S)-dihydroxy-5-methylhexyl]-6-phenyl-2(S)-(2-thienylmethyl)hexanamide (220588-85-2)

Guidance literature:

Multi-step reaction with 11 steps

1.1: dimethyl sulfoxide; oxalyl chloride; Et₃N / CH₂Cl₂ / 0.83 h / -78 °C

2.1: 4.82 g / diethyl ether / 1.25 h / -78 °C

3.1: O₃ / methanol / -78 °C

3.2: Me₂S / methanol / 4 h / -78 - 25 °C

4.1: 390 mg / Jones' reagent / acetone / 0.25 h / 0 - 20 °C

5.1: 84 percent / H₂ / Pd(OH)2/C / ethanol / 48 h

6.1: 87 percent / 2,6-lutidine / CH₂Cl₂ / 0.75 h / 0 - 25 °C

7.1: LDA / tetrahydrofuran; hexane / 0.5 h / -78 °C

7.2: 44 percent / HMPA / tetrahydrofuran; hexane / 3 h / -78 - -50 °C

8.1: aq. NaOH / tetrahydrofuran; methanol / 3.2 h / 0 °C

9.1: 2,6-lutidine / dimethylformamide / 15 h / 0 - 25 °C

10.1: 649 mg / K₂CO₃ / methanol; tetrahydrofuran; H₂O / 2.5 h / 25 °C

11.1: 582 mg / i-Pr₂NEt; BOP*PF₆ / CH₂Cl₂ / 3 h / 20 °C

With 2,6-dimethylpyridine; sodium hydroxide; jones' reagent; oxalyl dichloride; hydrogen; potassium carbonate; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; ozone; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; lithium diisopropyl amide; palladium dihydroxide; In tetrahydrofuran; methanol; diethyl ether; ethanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetone; 1.1: Swern oxidation / 2.1: Grignard reaction / 3.1: ozonation / 3.2: Reduction / 4.1: Oxidation / 5.1: Hydrogenolysis / 6.1: silylation / 7.1: Metallation / 7.2: Alkylation / 8.1: Hydrolysis / 9.1: silylation / 10.1: Hydrolysis / 11.1: Acylation;

DOI:10.1016/S0968-0896(98)80011-4

upstream raw materials:

(S)-2-amino-1-cyclohexyl-(R)-3,(S)-4-dihydroxy-6-methylheptane hydrochloride

(2S,4S,5S)-4,5-Bis-(tert-butyl-dimethyl-silanyloxy)-6-phenyl-2-thiophen-2-ylmethyl-hexanoic acid

L-3-phenyllactic acid

t-butyldimethylsiyl triflate