N-[1(S)-(cyclohexylmethyl)-2(R),3(S)-dihydroxy-5-methylhexyl]-2(R)-(cyclopropylmethyl)-5(S)-benzyloxy-4(S)-hydroxy-6-phenylhexanamide

Base Information

Chemical Name:N-[1(S)-(cyclohexylmethyl)-2(R),3(S)-dihydroxy-5-methylhexyl]-2(R)-(cyclopropylmethyl)-5(S)-benzyloxy-4(S)-hydroxy-6-phenylhexanamide
CAS No.:155295-62-8
Molecular Formula:C₃₇H₅₅NO₅
Molecular Weight:593.847
Hs Code.:

Synonyms:N-[1(S)-(cyclohexylmethyl)-2(R),3(S)-dihydroxy-5-methylhexyl]-2(R)-(cyclopropylmethyl)-5(S)-benzyloxy-4(S)-hydroxy-6-phenylhexanamide

Suppliers and Price of N-[1(S)-(cyclohexylmethyl)-2(R),3(S)-dihydroxy-5-methylhexyl]-2(R)-(cyclopropylmethyl)-5(S)-benzyloxy-4(S)-hydroxy-6-phenylhexanamide

Supply Marketing:

Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

Manufacturers and distributors:

Manufacture/Brand
Chemicals and raw materials
Packaging
price

Total 0 raw suppliers

Chemical Property of N-[1(S)-(cyclohexylmethyl)-2(R),3(S)-dihydroxy-5-methylhexyl]-2(R)-(cyclopropylmethyl)-5(S)-benzyloxy-4(S)-hydroxy-6-phenylhexanamide

Chemical Property:

Purity/Quality:

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:

Useful:

Technology Process of N-[1(S)-(cyclohexylmethyl)-2(R),3(S)-dihydroxy-5-methylhexyl]-2(R)-(cyclopropylmethyl)-5(S)-benzyloxy-4(S)-hydroxy-6-phenylhexanamide

There total 12 articles about N-[1(S)-(cyclohexylmethyl)-2(R),3(S)-dihydroxy-5-methylhexyl]-2(R)-(cyclopropylmethyl)-5(S)-benzyloxy-4(S)-hydroxy-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: 87.0%

: 155295-61-7
N-[1(S)-(cyclohexylmethyl)-2(R),3(S)-dihydroxy-5-methylhexyl]-5(S)-benzyloxy-4(S)-[(tert-butyldimethylsilyl)oxy]-2(R)-(cyclopropylmethyl)-6-phenylhexanamide

: 155295-62-8
N-[1(S)-(cyclohexylmethyl)-2(R),3(S)-dihydroxy-5-methylhexyl]-2(R)-(cyclopropylmethyl)-5(S)-benzyloxy-4(S)-hydroxy-6-phenylhexanamide

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 25 ℃; for 18.2h; Heating;
DOI:10.1016/S0968-0896(98)80011-4

Reference yield:

: 20312-36-1
L-3-phenyllactic acid

: 155295-62-8
N-[1(S)-(cyclohexylmethyl)-2(R),3(S)-dihydroxy-5-methylhexyl]-2(R)-(cyclopropylmethyl)-5(S)-benzyloxy-4(S)-hydroxy-6-phenylhexanamide

Guidance literature:: Multi-step reaction with 12 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: i-Pr₂NEt; BuLi / tetrahydrofuran; hexane / -78 - -65 °C

7.2: 76 percent / tetrahydrofuran; hexane / 2 h / -78 °C

8.1: 88 percent / Pd(OAc)2 / diethyl ether / 0.17 h / 0 °C

9.1: NaOH / methanol; H₂O / 2 h / 25 °C

9.2: 2,6-lutidine / CH₂Cl₂ / 18 h / 4 °C

10.1: NaHCO₃; citric acid / CH₂Cl₂; ethyl acetate; H₂O

11.1: 53.3 mg / i-Pr₂NEt; BOP*PF₆; HOBt / CH₂Cl₂ / 3 h / 25 °C / pH 8.0 - 8.5

12.1: 87 percent / TBAF / tetrahydrofuran / 18.2 h / 25 °C / Heating

With sodium hydroxide; lithium aluminium tetrahydride; n-butyllithium; jones' reagent; oxalyl dichloride; tetrabutyl ammonium fluoride; sodium hydride; sodium hydrogencarbonate; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; benzotriazol-1-ol; ozone; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; citric acid; palladium diacetate; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; ethyl acetate; 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: Metallation / 7.2: Alkylation / 8.1: Cycloaddition / 9.1: Hydrolysis / 9.2: silylation / 10.1: Hydrolysis / 11.1: Acylation / 12.1: desilylation;
DOI:10.1016/S0968-0896(98)80011-4

Reference yield:

: 118535-75-4
(2S)-2-benzyloxy-3-phenylpropanal

: 155295-62-8
N-[1(S)-(cyclohexylmethyl)-2(R),3(S)-dihydroxy-5-methylhexyl]-2(R)-(cyclopropylmethyl)-5(S)-benzyloxy-4(S)-hydroxy-6-phenylhexanamide

Guidance literature:: Multi-step reaction with 9 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: i-Pr₂NEt; BuLi / tetrahydrofuran; hexane / -78 - -65 °C

4.2: 76 percent / tetrahydrofuran; hexane / 2 h / -78 °C

5.1: 88 percent / Pd(OAc)2 / diethyl ether / 0.17 h / 0 °C

6.1: NaOH / methanol; H₂O / 2 h / 25 °C

6.2: 2,6-lutidine / CH₂Cl₂ / 18 h / 4 °C

7.1: NaHCO₃; citric acid / CH₂Cl₂; ethyl acetate; H₂O

8.1: 53.3 mg / i-Pr₂NEt; BOP*PF₆; HOBt / CH₂Cl₂ / 3 h / 25 °C / pH 8.0 - 8.5

9.1: 87 percent / TBAF / tetrahydrofuran / 18.2 h / 25 °C / Heating

With sodium hydroxide; n-butyllithium; jones' reagent; tetrabutyl ammonium fluoride; sodium hydrogencarbonate; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; benzotriazol-1-ol; ozone; N-ethyl-N,N-diisopropylamine; citric acid; palladium diacetate; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; ethyl acetate; acetone; 1.1: Grignard reaction / 2.1: ozonation / 2.2: Reduction / 3.1: Oxidation / 4.1: Metallation / 4.2: Alkylation / 5.1: Cycloaddition / 6.1: Hydrolysis / 6.2: silylation / 7.1: Hydrolysis / 8.1: Acylation / 9.1: desilylation;
DOI:10.1016/S0968-0896(98)80011-4