(S)-N-((1S,2R,3S)-1-Cyclohexylmethyl-2,3-dihydroxy-5-methyl-hexyl)-3-thiophen-2-ylmethyl-succinamic acid

Base Information

Chemical Name:(S)-N-((1S,2R,3S)-1-Cyclohexylmethyl-2,3-dihydroxy-5-methyl-hexyl)-3-thiophen-2-ylmethyl-succinamic acid
CAS No.:225378-33-6
Molecular Formula:C₂₃H₃₇NO₅S
Molecular Weight:439.616
Hs Code.:

Synonyms:(S)-N-((1S,2R,3S)-1-Cyclohexylmethyl-2,3-dihydroxy-5-methyl-hexyl)-3-thiophen-2-ylmethyl-succinamic acid

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Chemical Property of (S)-N-((1S,2R,3S)-1-Cyclohexylmethyl-2,3-dihydroxy-5-methyl-hexyl)-3-thiophen-2-ylmethyl-succinamic acid

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Technology Process of (S)-N-((1S,2R,3S)-1-Cyclohexylmethyl-2,3-dihydroxy-5-methyl-hexyl)-3-thiophen-2-ylmethyl-succinamic acid

There total 6 articles about (S)-N-((1S,2R,3S)-1-Cyclohexylmethyl-2,3-dihydroxy-5-methyl-hexyl)-3-thiophen-2-ylmethyl-succinamic acid 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: 86.0%

: 225377-83-3
N-<1(S)-(cyclohexylmethyl)-2(R),3(S)-dihydroxy-5-methylhexyl>-4-(1,1-dimethylethoxy)-4-oxo-2(S)-(2-thienylmethyl)butanamide

: 225378-33-6
(S)-N-((1S,2R,3S)-1-Cyclohexylmethyl-2,3-dihydroxy-5-methyl-hexyl)-3-thiophen-2-ylmethyl-succinamic acid

Guidance literature:: With trifluoroacetic acid; In dichloromethane; 1.) 0 deg C, 75 min, 2.) 25 deg C, 75 min;
DOI:10.1016/S0968-0896(98)00265-X

Reference yield:

: 5928-51-8
3-(2-thienyl)propanoic acid

: 225378-33-6
(S)-N-((1S,2R,3S)-1-Cyclohexylmethyl-2,3-dihydroxy-5-methyl-hexyl)-3-thiophen-2-ylmethyl-succinamic acid

Guidance literature:: Multi-step reaction with 5 steps

1: 1.) trimethylacetyl chloride, Et₃N / 1.) THF, 0 deg C, 30 min, 2.) THF, -78 deg C, 30 min; 0 deg C, 45 min

2: 79 percent / NaHMDS / tetrahydrofuran / -78 °C / 1.) 45 min, 2.) 2 h

3: 30 percent H₂O₂, LiOH*H₂O / tetrahydrofuran; H₂O / 25 °C

4: i-Pr₂NEt, BOP*PF₆ / dimethylformamide / 25 °C

5: 86 percent / TFA / CH₂Cl₂ / 1.) 0 deg C, 75 min, 2.) 25 deg C, 75 min

With lithium hydroxide; dihydrogen peroxide; sodium hexamethyldisilazane; pivaloyl chloride; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1016/S0968-0896(98)00265-X

Reference yield:

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

: 225378-33-6
(S)-N-((1S,2R,3S)-1-Cyclohexylmethyl-2,3-dihydroxy-5-methyl-hexyl)-3-thiophen-2-ylmethyl-succinamic acid

Guidance literature:: Multi-step reaction with 2 steps

1: i-Pr₂NEt, BOP*PF₆ / dimethylformamide / 25 °C

2: 86 percent / TFA / CH₂Cl₂ / 1.) 0 deg C, 75 min, 2.) 25 deg C, 75 min

With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/S0968-0896(98)00265-X