(Z)-(S)-3-tert-Butoxycarbonylamino-tetradec-5-enoic acid

Base Information

Chemical Name:(Z)-(S)-3-tert-Butoxycarbonylamino-tetradec-5-enoic acid
CAS No.:207407-18-9
Molecular Formula:C₁₉H₃₅NO₄
Molecular Weight:341.491
Hs Code.:

Synonyms:

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Chemical Property of (Z)-(S)-3-tert-Butoxycarbonylamino-tetradec-5-enoic acid

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Technology Process of (Z)-(S)-3-tert-Butoxycarbonylamino-tetradec-5-enoic acid

There total 11 articles about (Z)-(S)-3-tert-Butoxycarbonylamino-tetradec-5-enoic 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:

: 13488-14-7
tetradeca-2,5-diyn-1-ol

: 207407-18-9
(Z)-(S)-3-tert-Butoxycarbonylamino-tetradec-5-enoic acid

Guidance literature:: Multi-step reaction with 11 steps

1: 65 percent / LiAlH₄ / diethyl ether / 2 h / Ambient temperature

2: 1.) MS₄A, (+)-DET, Ti(OiPr)4, 2.) t-BuOOH / 1.) CH₂Cl₂, -23 deg C, 1 h, 2.) 2,2,4-trimethylpentane, -25 deg C, overnight

3: 90 percent / H₂, quinoline / Lindlar catalyst / methanol

4: 99 percent / bis(2-methoxyethoxy)aluminum hydride / tetrahydrofuran; toluene / 0 °C

5: imidazole / dimethylformamide / 0.5 h / 0 °C

6: Et₃N / CH₂Cl₂ / 1 h / 0 °C

7: NaN₃ / dimethylformamide / 50 °C

8: Ph₃P / tetrahydrofuran; H₂O / 45 °C

9: Et₃N / CH₂Cl₂ / Ambient temperature

10: 97 percent / Bu₄NF / tetrahydrofuran / 3 h / Ambient temperature

11: 1.) (COCl)2, DMSO, Et₃N, 2.) 2-methyl-2-butene, NaH₂PO₄*2H₂O, NaClO₄ / 1.) CH₂Cl₂, 0 deg C, 1 h, 2.) 2-methyl-2-propanol, H₂O, 30 min

With 1H-imidazole; quinoline; titanium(IV) isopropylate; tert.-butylhydroperoxide; sodium dihydrogenphosphate; lithium aluminium tetrahydride; sodium azide; 2-methyl-but-2-ene; oxalyl dichloride; diethyl (2R,3R)-tartrate; sodium perchlorate; tetrabutyl ammonium fluoride; hydrogen; sodium dihydro-bis-(2-methoxyethoxy)aluminate; dimethyl sulfoxide; triethylamine; triphenylphosphine; Lindlar's catalyst; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jo9722461

Reference yield:

: 207407-05-4
(E)-tetradec-2-en-5-yn-1-ol

: 207407-18-9
(Z)-(S)-3-tert-Butoxycarbonylamino-tetradec-5-enoic acid

Guidance literature:: Multi-step reaction with 10 steps

1: 1.) MS₄A, (+)-DET, Ti(OiPr)4, 2.) t-BuOOH / 1.) CH₂Cl₂, -23 deg C, 1 h, 2.) 2,2,4-trimethylpentane, -25 deg C, overnight

2: 90 percent / H₂, quinoline / Lindlar catalyst / methanol

3: 99 percent / bis(2-methoxyethoxy)aluminum hydride / tetrahydrofuran; toluene / 0 °C

4: imidazole / dimethylformamide / 0.5 h / 0 °C

5: Et₃N / CH₂Cl₂ / 1 h / 0 °C

6: NaN₃ / dimethylformamide / 50 °C

7: Ph₃P / tetrahydrofuran; H₂O / 45 °C

8: Et₃N / CH₂Cl₂ / Ambient temperature

9: 97 percent / Bu₄NF / tetrahydrofuran / 3 h / Ambient temperature

10: 1.) (COCl)2, DMSO, Et₃N, 2.) 2-methyl-2-butene, NaH₂PO₄*2H₂O, NaClO₄ / 1.) CH₂Cl₂, 0 deg C, 1 h, 2.) 2-methyl-2-propanol, H₂O, 30 min

With 1H-imidazole; quinoline; titanium(IV) isopropylate; tert.-butylhydroperoxide; sodium dihydrogenphosphate; sodium azide; 2-methyl-but-2-ene; oxalyl dichloride; diethyl (2R,3R)-tartrate; sodium perchlorate; tetrabutyl ammonium fluoride; hydrogen; sodium dihydro-bis-(2-methoxyethoxy)aluminate; dimethyl sulfoxide; triethylamine; triphenylphosphine; Lindlar's catalyst; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jo9722461

Reference yield:

: (2S,3R)-2,3-epoxytetradec-5-yn-1-ol

: 207407-18-9
(Z)-(S)-3-tert-Butoxycarbonylamino-tetradec-5-enoic acid

Guidance literature:: Multi-step reaction with 9 steps

1: 90 percent / H₂, quinoline / Lindlar catalyst / methanol

2: 99 percent / bis(2-methoxyethoxy)aluminum hydride / tetrahydrofuran; toluene / 0 °C

3: imidazole / dimethylformamide / 0.5 h / 0 °C

4: Et₃N / CH₂Cl₂ / 1 h / 0 °C

5: NaN₃ / dimethylformamide / 50 °C

6: Ph₃P / tetrahydrofuran; H₂O / 45 °C

7: Et₃N / CH₂Cl₂ / Ambient temperature

8: 97 percent / Bu₄NF / tetrahydrofuran / 3 h / Ambient temperature

9: 1.) (COCl)2, DMSO, Et₃N, 2.) 2-methyl-2-butene, NaH₂PO₄*2H₂O, NaClO₄ / 1.) CH₂Cl₂, 0 deg C, 1 h, 2.) 2-methyl-2-propanol, H₂O, 30 min

With 1H-imidazole; quinoline; sodium dihydrogenphosphate; sodium azide; 2-methyl-but-2-ene; oxalyl dichloride; sodium perchlorate; tetrabutyl ammonium fluoride; hydrogen; sodium dihydro-bis-(2-methoxyethoxy)aluminate; dimethyl sulfoxide; triethylamine; triphenylphosphine; Lindlar's catalyst; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jo9722461