(1'R,5'S,7'R,1''R)-4-{1'-[2''-benzyloxy-1''-methyl-ethyl]-6'-trifluoroacetyl-6'-aza-5'-spiro[4.5]dec-7'-yl}-2-methylbut-2E-enoic acid ethyl ester

Base Information

Chemical Name:(1'R,5'S,7'R,1''R)-4-{1'-[2''-benzyloxy-1''-methyl-ethyl]-6'-trifluoroacetyl-6'-aza-5'-spiro[4.5]dec-7'-yl}-2-methylbut-2E-enoic acid ethyl ester
CAS No.:857685-75-7
Molecular Formula:C₂₈H₃₈F₃NO₄
Molecular Weight:509.609
Hs Code.:

Synonyms:(1'R,5'S,7'R,1''R)-4-{1'-[2''-benzyloxy-1''-methyl-ethyl]-6'-trifluoroacetyl-6'-aza-5'-spiro[4.5]dec-7'-yl}-2-methylbut-2E-enoic acid ethyl ester

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Chemical Property of (1'R,5'S,7'R,1''R)-4-{1'-[2''-benzyloxy-1''-methyl-ethyl]-6'-trifluoroacetyl-6'-aza-5'-spiro[4.5]dec-7'-yl}-2-methylbut-2E-enoic acid ethyl ester

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Technology Process of (1'R,5'S,7'R,1''R)-4-{1'-[2''-benzyloxy-1''-methyl-ethyl]-6'-trifluoroacetyl-6'-aza-5'-spiro[4.5]dec-7'-yl}-2-methylbut-2E-enoic acid ethyl ester

There total 21 articles about (1'R,5'S,7'R,1''R)-4-{1'-[2''-benzyloxy-1''-methyl-ethyl]-6'-trifluoroacetyl-6'-aza-5'-spiro[4.5]dec-7'-yl}-2-methylbut-2E-enoic acid ethyl ester 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: 90.0%

: 857685-74-6
[(1R,5S,7R)-1-((R)-2-Benzyloxy-1-methyl-ethyl)-6-(2,2,2-trifluoro-acetyl)-6-aza-spiro[4.5]dec-7-yl]-acetaldehyde

: 3699-66-9
ethyl 2-diethoxyphosphorylpropionate

: 857685-75-7
(1'R,5'S,7'R,1''R)-4-{1'-[2''-benzyloxy-1''-methyl-ethyl]-6'-trifluoroacetyl-6'-aza-5'-spiro[4.5]dec-7'-yl}-2-methylbut-2E-enoic acid ethyl ester

Guidance literature:: With sodium hydride; In tetrahydrofuran; at 0 - 20 ℃; for 1.33333h;
DOI:10.1021/jo047882v

Reference yield:

: 857685-61-1
(2R)-2-((1R)-2-benzyloxy-1-methylethyl)-cyclopentanone oxime

: 857685-75-7
(1'R,5'S,7'R,1''R)-4-{1'-[2''-benzyloxy-1''-methyl-ethyl]-6'-trifluoroacetyl-6'-aza-5'-spiro[4.5]dec-7'-yl}-2-methylbut-2E-enoic acid ethyl ester

Guidance literature:: Multi-step reaction with 13 steps

1.1: m-CPBA; Na₂HPO₄; urea / acetonitrile / 80 °C

2.1: Triton B / methanol; tetrahydrofuran; 2-methyl-propan-2-ol / 48 h / 20 °C

3.1: LiBH₄ / tetrahydrofuran / 24 h / 20 °C

4.1: triethylamine; 4-(dimethylamino)pyridine / CH₂Cl₂ / 2 h / 0 - 20 °C

5.1: sodium iodide; sodium hydrogen carbonate / acetone / 24 h / 20 °C

6.1: t-BuLi; HMPA / tetrahydrofuran; pentane / 0.5 h / -78 °C

6.2: tetrahydrofuran; pentane / 3 h / -78 °C

7.1: iodine; sodium hydrogen carbonate / acetone; H₂O / 1 h / 0 °C

8.1: hydrogen; triethylamine / Raney nickel / cyclohexane / 4 h / 25 °C / 760.05 Torr

9.1: NaBH₄ / CH₂Cl₂; methanol / 0 - 20 °C

10.1: i-Pr₂NEt / 1,2-dichloro-ethane / 1 h / 0 °C

11.1: HF*pyridine complex / tetrahydrofuran / 20 °C

12.1: DMP / CH₂Cl₂ / 5 h / 20 °C

13.1: sodium hydride / tetrahydrofuran / 0.5 h / 0 °C

13.2: tetrahydrofuran / 0 - 20 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; sodium tetrahydroborate; disodium hydrogenphosphate; lithium borohydride; phthalic acid dimethyl ester; hydrogen; iodine; tert.-butyl lithium; N-benzyl-trimethylammonium hydroxide; sodium hydride; sodium hydrogencarbonate; pyridine hydrogenfluoride; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; urea; sodium iodide; nickel; In tetrahydrofuran; methanol; dichloromethane; cyclohexane; water; 1,2-dichloro-ethane; acetone; acetonitrile; tert-butyl alcohol; pentane; 2.1: Michael addition / 13.2: Horner-Wadsworth-Emmons reaction;
DOI:10.1016/j.tet.2007.03.031

Reference yield:

: 857685-64-4
(1R,2S)-1-((1R)-2-benzyloxy-1-methylethyl)-2-(3-hydroxypropyl)-2-nitro-cyclopentane

: 857685-75-7
(1'R,5'S,7'R,1''R)-4-{1'-[2''-benzyloxy-1''-methyl-ethyl]-6'-trifluoroacetyl-6'-aza-5'-spiro[4.5]dec-7'-yl}-2-methylbut-2E-enoic acid ethyl ester

Guidance literature:: Multi-step reaction with 10 steps

1.1: triethylamine; 4-(dimethylamino)pyridine / CH₂Cl₂ / 2 h / 0 - 20 °C

2.1: sodium iodide; sodium hydrogen carbonate / acetone / 24 h / 20 °C

3.1: t-BuLi; HMPA / tetrahydrofuran; pentane / 0.5 h / -78 °C

3.2: tetrahydrofuran; pentane / 3 h / -78 °C

4.1: iodine; sodium hydrogen carbonate / acetone; H₂O / 1 h / 0 °C

5.1: hydrogen; triethylamine / Raney nickel / cyclohexane / 4 h / 25 °C / 760.05 Torr

6.1: NaBH₄ / CH₂Cl₂; methanol / 0 - 20 °C

7.1: i-Pr₂NEt / 1,2-dichloro-ethane / 1 h / 0 °C

8.1: HF*pyridine complex / tetrahydrofuran / 20 °C

9.1: DMP / CH₂Cl₂ / 5 h / 20 °C

10.1: sodium hydride / tetrahydrofuran / 0.5 h / 0 °C

10.2: tetrahydrofuran / 0 - 20 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; sodium tetrahydroborate; phthalic acid dimethyl ester; hydrogen; iodine; tert.-butyl lithium; sodium hydride; sodium hydrogencarbonate; pyridine hydrogenfluoride; triethylamine; N-ethyl-N,N-diisopropylamine; sodium iodide; nickel; In tetrahydrofuran; methanol; dichloromethane; cyclohexane; water; 1,2-dichloro-ethane; acetone; pentane; 10.2: Horner-Wadsworth-Emmons reaction;
DOI:10.1016/j.tet.2007.03.031