N-[1(S)-(cyclohexylmethyl)-2(R),3(S)-dihydroxy-5-methylhexyl]-2(R)-(cyclopropylmethyl)-3(R),5(S)-dihydroxy-3,5-O-isopropylidene-6-phenylhexanamide

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Chemical Name:N-[1(S)-(cyclohexylmethyl)-2(R),3(S)-dihydroxy-5-methylhexyl]-2(R)-(cyclopropylmethyl)-3(R),5(S)-dihydroxy-3,5-O-isopropylidene-6-phenylhexanamide
CAS No.:220588-92-1
Molecular Formula:C₃₃H₅₃NO₅
Molecular Weight:543.788
Hs Code.:

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

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

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

There total 6 articles about N-[1(S)-(cyclohexylmethyl)-2(R),3(S)-dihydroxy-5-methylhexyl]-2(R)-(cyclopropylmethyl)-3(R),5(S)-dihydroxy-3,5-O-isopropylidene-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:

: 104882-45-3
(S)-2-amino-1-cyclohexyl-(R)-3,(S)-4-dihydroxy-6-methylheptane hydrochloride

: 220588-91-0
(R)-2-((4R,6S)-6-Benzyl-2,2-dimethyl-[1,3]dioxan-4-yl)-3-cyclopropyl-propionic acid

: 220588-92-1
N-[1(S)-(cyclohexylmethyl)-2(R),3(S)-dihydroxy-5-methylhexyl]-2(R)-(cyclopropylmethyl)-3(R),5(S)-dihydroxy-3,5-O-isopropylidene-6-phenylhexanamide

Guidance literature:: With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In acetonitrile; at 25 ℃; for 1h;
DOI:10.1016/S0968-0896(98)80011-4

Reference yield:

: 155295-65-1,289677-11-8
3-(3-cyclopropyl-1-oxopropyl)-4(S)-phenylmethyl-2-oxazolidinone

: 220588-92-1
N-[1(S)-(cyclohexylmethyl)-2(R),3(S)-dihydroxy-5-methylhexyl]-2(R)-(cyclopropylmethyl)-3(R),5(S)-dihydroxy-3,5-O-isopropylidene-6-phenylhexanamide

Guidance literature:: Multi-step reaction with 6 steps

1.1: i-Pr₂NH; n-BuLi / tetrahydrofuran; hexane / 0.75 h / -78 °C

1.2: 51 percent / tetrahydrofuran; hexane / -78 - 20 °C

2.1: TiCl₄; i-Pr₂NEt / CH₂Cl₂ / 1 h / -15 °C

2.2: CH₂Cl₂ / 1 h / -78 - -10 °C

3.1: NaBH(OAc)3 / acetic acid / 1 h / 25 °C

4.1: 81 mg / p-TsOH / dimethylformamide / 1 h / 25 °C

5.1: 100 percent / H₂O₂; LiOH / tetrahydrofuran; H₂O / 0 - 25 °C

6.1: 180 mg / i-Pr₂NEt; BOP*PF₆ / acetonitrile / 1 h / 25 °C

With lithium hydroxide; n-butyllithium; dihydrogen peroxide; titanium tetrachloride; sodium tris(acetoxy)borohydride; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; toluene-4-sulfonic acid; diisopropylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; hexane; dichloromethane; water; acetic acid; N,N-dimethyl-formamide; acetonitrile; 1.1: Metallation / 1.2: Acetylation / 2.1: Metallation / 2.2: Condensation / 3.1: Reduction / 4.1: Cyclization / 5.1: Hydrolysis / 6.1: Acylation;
DOI:10.1016/S0968-0896(98)80011-4

Reference yield:

: 155295-74-2
3-[2(R)-(cyclopropylmethyl)-1,3-dioxobutyl]-4(S)-(phenylmethyl)-2-oxazolidinone

: 220588-92-1
N-[1(S)-(cyclohexylmethyl)-2(R),3(S)-dihydroxy-5-methylhexyl]-2(R)-(cyclopropylmethyl)-3(R),5(S)-dihydroxy-3,5-O-isopropylidene-6-phenylhexanamide

Guidance literature:: Multi-step reaction with 5 steps

1.1: TiCl₄; i-Pr₂NEt / CH₂Cl₂ / 1 h / -15 °C

1.2: CH₂Cl₂ / 1 h / -78 - -10 °C

2.1: NaBH(OAc)3 / acetic acid / 1 h / 25 °C

3.1: 81 mg / p-TsOH / dimethylformamide / 1 h / 25 °C

4.1: 100 percent / H₂O₂; LiOH / tetrahydrofuran; H₂O / 0 - 25 °C

5.1: 180 mg / i-Pr₂NEt; BOP*PF₆ / acetonitrile / 1 h / 25 °C

With lithium hydroxide; dihydrogen peroxide; titanium tetrachloride; sodium tris(acetoxy)borohydride; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; toluene-4-sulfonic acid; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; water; acetic acid; N,N-dimethyl-formamide; acetonitrile; 1.1: Metallation / 1.2: Condensation / 2.1: Reduction / 3.1: Cyclization / 4.1: Hydrolysis / 5.1: Acylation;
DOI:10.1016/S0968-0896(98)80011-4