(-)-S-4-(N,N-dibenzylamino)-6-phenyl-5-hexynyl 2,2,4,4-tetramethyl-1,3-oxazolidine-3-carboxylate

Base Information

Chemical Name:(-)-S-4-(N,N-dibenzylamino)-6-phenyl-5-hexynyl 2,2,4,4-tetramethyl-1,3-oxazolidine-3-carboxylate
CAS No.:205068-01-5
Molecular Formula:C₃₄H₄₀N₂O₃
Molecular Weight:524.703
Hs Code.:

Synonyms:(-)-S-4-(N,N-dibenzylamino)-6-phenyl-5-hexynyl 2,2,4,4-tetramethyl-1,3-oxazolidine-3-carboxylate

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Chemical Property of (-)-S-4-(N,N-dibenzylamino)-6-phenyl-5-hexynyl 2,2,4,4-tetramethyl-1,3-oxazolidine-3-carboxylate

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Technology Process of (-)-S-4-(N,N-dibenzylamino)-6-phenyl-5-hexynyl 2,2,4,4-tetramethyl-1,3-oxazolidine-3-carboxylate

There total 12 articles about (-)-S-4-(N,N-dibenzylamino)-6-phenyl-5-hexynyl 2,2,4,4-tetramethyl-1,3-oxazolidine-3-carboxylate 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: 88.0%

: 146176-60-5
2,2,4,4-tetramethyl-1,3-oxazolidine-3-carbonyl chloride

: 205068-07-1
(-)-S-4-(N,N-dibenzylamino)-6-phenyl-5-hexyn-1-ol

: 205068-01-5
(-)-S-4-(N,N-dibenzylamino)-6-phenyl-5-hexynyl 2,2,4,4-tetramethyl-1,3-oxazolidine-3-carboxylate

Guidance literature:: With sodium hydride; In tetrahydrofuran; Heating;
DOI:10.1016/S0040-4039(98)00085-9

Reference yield:

: 205068-02-6
(-)-S-5-(tert-butyldimethylsilyloxy)-2-(N,N-dibenzylamino)-1-pentanal

: 205068-01-5
(-)-S-4-(N,N-dibenzylamino)-6-phenyl-5-hexynyl 2,2,4,4-tetramethyl-1,3-oxazolidine-3-carboxylate

Guidance literature:: Multi-step reaction with 5 steps

1: 69 percent / PPh₃ / CH₂Cl₂ / 1 h / 0 °C

2: 93 percent / n-BuLi / tetrahydrofuran / -78 - 20 °C

3: 94 percent / Pd(PPh₃)2Cl₂; CuI; Et₃N / 6 h / 20 °C

4: 94 percent / TBAF / tetrahydrofuran / 20 °C

5: 64 percent / NaH / tetrahydrofuran / Heating

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; n-butyllithium; tetrabutyl ammonium fluoride; sodium hydride; triethylamine; triphenylphosphine; In tetrahydrofuran; dichloromethane; 1: Substitution / 2: Elimination / 3: Sonogashira coupling / 4: Substitution / 5: Acylation;
DOI:10.1021/jo991095u

Reference yield:

: 205068-04-8
(S)-2-(N,N-dibenzylamino)-5-(tert-butyldimethylsilyloxy)pentan-1-ol

: 205068-01-5
(-)-S-4-(N,N-dibenzylamino)-6-phenyl-5-hexynyl 2,2,4,4-tetramethyl-1,3-oxazolidine-3-carboxylate

Guidance literature:: Multi-step reaction with 6 steps

1: 90 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

2: 69 percent / PPh₃ / CH₂Cl₂ / 1 h / 0 °C

3: 93 percent / n-BuLi / tetrahydrofuran / -78 - 20 °C

4: 94 percent / Pd(PPh₃)2Cl₂; CuI; Et₃N / 6 h / 20 °C

5: 94 percent / TBAF / tetrahydrofuran / 20 °C

6: 64 percent / NaH / tetrahydrofuran / Heating

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; n-butyllithium; oxalyl dichloride; tetrabutyl ammonium fluoride; sodium hydride; dimethyl sulfoxide; triethylamine; triphenylphosphine; In tetrahydrofuran; dichloromethane; 1: Swern oxidation / 2: Substitution / 3: Elimination / 4: Sonogashira coupling / 5: Substitution / 6: Acylation;
DOI:10.1021/jo991095u