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

Base Information

Chemical Name:(S)-4-(tert-butyldimethylsilyloxy)-6-phenyl-5-hexynyl 2,2,4,4-tetramethyl-1,3-oxazolidine-3-carboxylate
CAS No.:257629-59-7
Molecular Formula:C₃₆H₄₅NO₄Si
Molecular Weight:583.843
Hs Code.:

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

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

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

There total 10 articles about (S)-4-(tert-butyldimethylsilyloxy)-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: 98.0%

: 58479-61-1
tert-butylchlorodiphenylsilane

: 253882-01-8
(+)-(S)-4-hydroxy-6-phenyl-5-hexynyl 2,2,4,4-tetramethyl-1,3-oxazolidine-3-carboxylate

: 257629-59-7
(S)-4-(tert-butyldimethylsilyloxy)-6-phenyl-5-hexynyl 2,2,4,4-tetramethyl-1,3-oxazolidine-3-carboxylate

Guidance literature:: With dmap; triethylamine; In dichloromethane; Heating;
DOI:10.1016/S0040-4039(98)00085-9

Reference yield:

: 205068-11-7
4-oxo-6-phenyl-5-hexynyl 2,2,4,4-tetramethyl-1,3-oxazolidine-3-carboxylate

: 257629-59-7
(S)-4-(tert-butyldimethylsilyloxy)-6-phenyl-5-hexynyl 2,2,4,4-tetramethyl-1,3-oxazolidine-3-carboxylate

Guidance literature:: Multi-step reaction with 2 steps

1: (R)-Alpine-borane / tetrahydrofuran / 0 - 20 °C

2: 94 percent / Et₃N; DMAP / CH₂Cl₂ / Heating

With dmap; B-isopinocampheyl-9-borabicyclo[3.3.1]nonane; triethylamine; In tetrahydrofuran; dichloromethane; 1: Reduction / 2: Substitution;
DOI:10.1021/jo991095u

Reference yield:

: 536-74-3
phenylacetylene

: 257629-59-7
(S)-4-(tert-butyldimethylsilyloxy)-6-phenyl-5-hexynyl 2,2,4,4-tetramethyl-1,3-oxazolidine-3-carboxylate

Guidance literature:: Multi-step reaction with 4 steps

1: 99 percent / n-BuLi / tetrahydrofuran / -78 - -18 °C

2: 69 percent / PCC; NaOAc / CH₂Cl₂ / 0 - 20 °C

3: (R)-Alpine-borane / tetrahydrofuran / 0 - 20 °C

4: 94 percent / Et₃N; DMAP / CH₂Cl₂ / Heating

With dmap; n-butyllithium; B-isopinocampheyl-9-borabicyclo[3.3.1]nonane; sodium acetate; triethylamine; pyridinium chlorochromate; In tetrahydrofuran; dichloromethane; 1: Addition / 2: Oxidation / 3: Reduction / 4: Substitution;
DOI:10.1021/jo991095u