(2S,3R)-2-(t-butoxycarbonylamino)-1-(t-butyldimethylsilanyloxy)-3-benzyloxyheptadecane

Base Information

Chemical Name:(2S,3R)-2-(t-butoxycarbonylamino)-1-(t-butyldimethylsilanyloxy)-3-benzyloxyheptadecane
CAS No.:693288-26-5
Molecular Formula:C₃₅H₆₅NO₄Si
Molecular Weight:591.991
Hs Code.:

Synonyms:(2S,3R)-2-(t-butoxycarbonylamino)-1-(t-butyldimethylsilanyloxy)-3-benzyloxyheptadecane

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Chemical Property of (2S,3R)-2-(t-butoxycarbonylamino)-1-(t-butyldimethylsilanyloxy)-3-benzyloxyheptadecane

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Technology Process of (2S,3R)-2-(t-butoxycarbonylamino)-1-(t-butyldimethylsilanyloxy)-3-benzyloxyheptadecane

There total 7 articles about (2S,3R)-2-(t-butoxycarbonylamino)-1-(t-butyldimethylsilanyloxy)-3-benzyloxyheptadecane 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: 73.0%

: 100-39-0
benzyl bromide

: 693288-25-4
(2S,3R)-2-(t-butoxycarbonylamino)-1-(t-butyldimethylsilanyloxy)heptadecan-3-ol

: 693288-26-5
(2S,3R)-2-(t-butoxycarbonylamino)-1-(t-butyldimethylsilanyloxy)-3-benzyloxyheptadecane

Guidance literature:: With tetra-(n-butyl)ammonium iodide; sodium hydride; In N,N-dimethyl-formamide; at 0 - 20 ℃;
DOI:10.1021/jo030355b

Reference yield:

: 3262-72-4
(S)-N-(tert-butoxycarbonyl)serine

: 693288-26-5
(2S,3R)-2-(t-butoxycarbonylamino)-1-(t-butyldimethylsilanyloxy)-3-benzyloxyheptadecane

Guidance literature:: Multi-step reaction with 5 steps

1: 86 percent / N-methylmorpholine; 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride / CH₂Cl₂ / 1.58 h / -15 °C

2: 95 percent / DMAP; imidazole / dimethylformamide

3: 44 percent / t-BuLi / -78 - 20 °C

4: 94 percent / LiAl(O-t-Bu)3H / ethanol / 6 h / -78 °C

5: 73 percent / tetrabutylammonium iodide; NaH / dimethylformamide / 0 - 20 °C

With 4-methyl-morpholine; 1H-imidazole; dmap; tert.-butyl lithium; tetra-(n-butyl)ammonium iodide; sodium hydride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; lithium tri-t-butoxyaluminum hydride; In ethanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo030355b

Reference yield:

: 122709-20-0
N-(tert-butoxycarbonyl)-L-serine N'-methoxy-N'-methylamide

: 693288-26-5
(2S,3R)-2-(t-butoxycarbonylamino)-1-(t-butyldimethylsilanyloxy)-3-benzyloxyheptadecane

Guidance literature:: Multi-step reaction with 4 steps

1: 95 percent / DMAP; imidazole / dimethylformamide

2: 44 percent / t-BuLi / -78 - 20 °C

3: 94 percent / LiAl(O-t-Bu)3H / ethanol / 6 h / -78 °C

4: 73 percent / tetrabutylammonium iodide; NaH / dimethylformamide / 0 - 20 °C

With 1H-imidazole; dmap; tert.-butyl lithium; tetra-(n-butyl)ammonium iodide; sodium hydride; lithium tri-t-butoxyaluminum hydride; In ethanol; N,N-dimethyl-formamide;
DOI:10.1021/jo030355b