e.g. Filippa Pettersson or Cancer Res. 75(6) , 1102-12, (2015) or 10.1002/anie.201600521

Asymmetric synthesis of α, α-disubstituted α-amino alcohol derivatives

T Nakamura, T Tsuji, Y Iio, S Miyazaki, T Takemoto…

Index: Nakamura, Tsuyoshi; Tsuji, Takashi; Iio, Yukiko; Miyazaki, Shojiro; Takemoto, Toshiyasu; Nishi, Takahide Tetrahedron Asymmetry, 2006 , vol. 17, # 19 p. 2781 - 2792

Full Text: HTML

Citation Number: 18

Abstract

We herein report an asymmetric synthesis of α, α-disubstituted α-amino alcohol derivatives 3, key intermediates of a novel immunomodulator, using enzymatic desymmetrization of 2- alkyl-2-tert-butoxycarbonylamino-1, 3-propanediols 1a and 1b. This method makes it possible to prepare a chiral analogue of FTY720 4. These synthetic procedures allow for a broad structure variation in order to evaluate structure–activity relationships and the ...

(2R)-tert-butoxycarbonylamino-1-n-hexanoyloxy-2-methyl-4-(1-methylpyrrol-2-yl)-3-butene Structure

(2R)-tert-butox...

~%

(4R)-4-methyl-4-[2-(1-methylpyrrol-2-yl)ethenyl]-1,3-oxazolidin-2-one Structure

(4R)-4-methyl-4...

(2S)-tert-butoxycarbonylamino-3-n-hexanoyloxy-2-methyl-1-propanal Structure

(2S)-tert-butox...

~%

(4R)-4-methyl-4-[2-(1-methylpyrrol-2-yl)ethenyl]-1,3-oxazolidin-2-one Structure

(4R)-4-methyl-4...

Carbamic acid, [2-hydroxy-1-(hydroxymethyl)-1-methylethyl]-, 1,1-dimethylethyl Structure

Carbamic acid, ...

~%

(4R)-4-methyl-4-[2-(1-methylpyrrol-2-yl)ethenyl]-1,3-oxazolidin-2-one Structure

(4R)-4-methyl-4...

(2S)-tert-butoxycarbonylamino-3-n-hexanoyloxy-2-methyl-1-propanal Structure

(2S)-tert-butox...

~%

(4R)-4-methyl-4-(2-thiophen-2-ylethenyl)-1,3-oxazolidin-2-one Structure

(4R)-4-methyl-4...

(2R)-tert-butoxycarbonylamino-3-n-hexanoyloxy-2-methyl-1-propanol Structure

(2R)-tert-butox...

~%

(4R)-4-methyl-4-(2-thiophen-2-ylethenyl)-1,3-oxazolidin-2-one Structure

(4R)-4-methyl-4...

2-THIENYLTRIPHENYLPHOSPHONIUM BROMIDE Structure

2-THIENYLTRIPHE...

~%

(4R)-4-methyl-4-(2-thiophen-2-ylethenyl)-1,3-oxazolidin-2-one Structure

(4R)-4-methyl-4...

Carbamic acid, [2-hydroxy-1-(hydroxymethyl)-1-methylethyl]-, 1,1-dimethylethyl Structure

Carbamic acid, ...

~%

(4R)-4-methyl-4-(2-thiophen-2-ylethenyl)-1,3-oxazolidin-2-one Structure

(4R)-4-methyl-4...

(2R)-tert-butoxycarbonylamino-3-n-hexanoyloxy-2-methyl-1-propanol Structure

(2R)-tert-butox...

~%

(4R)-4-methyl-4-[2-(1-methylpyrrol-2-yl)ethenyl]-1,3-oxazolidin-2-one Structure

(4R)-4-methyl-4...

(2R)-tert-butoxycarbonylamino-3-n-hexanoyloxy-2-methyl-1-propanol Structure

(2R)-tert-butox...

~%

(4R)-4-methyl-4-[2-(1-methylpyrrol-2-yl)ethyl]-1,3-oxazolidin-2-one Structure

(4R)-4-methyl-4...

Carbamic acid, [2-hydroxy-1-(hydroxymethyl)-1-methylethyl]-, 1,1-dimethylethyl Structure

Carbamic acid, ...

~%

(4R)-4-methyl-4-[2-(1-methylpyrrol-2-yl)ethyl]-1,3-oxazolidin-2-one Structure

(4R)-4-methyl-4...

Carbamic acid, [1,1-bis(hydroxymethyl)propyl]-, 1,1-dimethylethyl ester (9CI) Structure

Carbamic acid, ...

~%

2-Oxazolidinone,4-ethyl-4-[2-(2-furanyl)ethenyl]-,(4R)-(9CI) Structure

2-Oxazolidinone...

(2S)-tert-butoxycarbonylamino-2-ethyl-3-n-hexanoyloxy-1-propanal Structure

(2S)-tert-butox...

~%

2-Oxazolidinone,4-ethyl-4-[2-(2-furanyl)ethenyl]-,(4R)-(9CI) Structure

2-Oxazolidinone...

(2R)-tert-butoxycarbonylamino-3-n-hexanoyloxy-2-ethyl-1-propanol Structure

(2R)-tert-butox...

~%

2-Oxazolidinone,4-ethyl-4-[2-(2-furanyl)ethenyl]-,(4R)-(9CI) Structure

2-Oxazolidinone...

(2R)-tert-butoxycarbonylamino-2-ethyl-1-n-hexanoyloxy-4-(thiophen-2-yl)-3-butene Structure

(2R)-tert-butox...

~%

(4R)-4-ethyl-4-(2-thiophen-2-ylethenyl)-1,3-oxazolidin-2-one Structure

(4R)-4-ethyl-4-...

Carbamic acid, [1,1-bis(hydroxymethyl)propyl]-, 1,1-dimethylethyl ester (9CI) Structure

Carbamic acid, ...

~%

(4R)-4-ethyl-4-(2-thiophen-2-ylethenyl)-1,3-oxazolidin-2-one Structure

(4R)-4-ethyl-4-...

(2S)-tert-butoxycarbonylamino-2-ethyl-3-n-hexanoyloxy-1-propanal Structure

(2S)-tert-butox...

~%

(4R)-4-ethyl-4-(2-thiophen-2-ylethenyl)-1,3-oxazolidin-2-one Structure

(4R)-4-ethyl-4-...

(2R)-tert-butoxycarbonylamino-3-n-hexanoyloxy-2-ethyl-1-propanol Structure

(2R)-tert-butox...

~%

(4R)-4-ethyl-4-(2-thiophen-2-ylethenyl)-1,3-oxazolidin-2-one Structure

(4R)-4-ethyl-4-...

2-THIENYLTRIPHENYLPHOSPHONIUM BROMIDE Structure

2-THIENYLTRIPHE...

~%

(4R)-4-ethyl-4-(2-thiophen-2-ylethenyl)-1,3-oxazolidin-2-one Structure

(4R)-4-ethyl-4-...

(2S)-tert-butoxycarbonylamino-3-n-hexanoyloxy-2-methyl-1-propanal Structure

(2S)-tert-butox...

~%

(4R)-4-[2-(furan-2-yl)ethenyl]-4-methyl-1,3-oxazolidin-2-one Structure

(4R)-4-[2-(fura...

(2R)-tert-butoxycarbonylamino-3-n-hexanoyloxy-2-methyl-1-propanol Structure

(2R)-tert-butox...

~%

(4R)-4-[2-(furan-2-yl)ethenyl]-4-methyl-1,3-oxazolidin-2-one Structure

(4R)-4-[2-(fura...

Carbamic acid, [2-hydroxy-1-(hydroxymethyl)-1-methylethyl]-, 1,1-dimethylethyl Structure

Carbamic acid, ...

~%

(4R)-4-[2-(furan-2-yl)ethenyl]-4-methyl-1,3-oxazolidin-2-one Structure

(4R)-4-[2-(fura...

(R)-2-((tert-butoxycarbonyl)amino)-2-methyl-4-(3-methylthiophen-2-yl)but-3-en-1-yl hexanoate Structure

(R)-2-((tert-bu...

~%

2-Oxazolidinone,4-methyl-4-[2-(3-methyl-2-thienyl)ethenyl]-,(4R)-(9CI) Structure

2-Oxazolidinone...

(2S)-tert-butoxycarbonylamino-3-n-hexanoyloxy-2-methyl-1-propanal Structure

(2S)-tert-butox...

~%

2-Oxazolidinone,4-methyl-4-[2-(3-methyl-2-thienyl)ethenyl]-,(4R)-(9CI) Structure

2-Oxazolidinone...

(2R)-tert-butoxycarbonylamino-3-n-hexanoyloxy-2-methyl-1-propanol Structure

(2R)-tert-butox...

~%

2-Oxazolidinone,4-methyl-4-[2-(3-methyl-2-thienyl)ethenyl]-,(4R)-(9CI) Structure

2-Oxazolidinone...

Carbamic acid, [2-hydroxy-1-(hydroxymethyl)-1-methylethyl]-, 1,1-dimethylethyl Structure

Carbamic acid, ...

~%

2-Oxazolidinone,4-methyl-4-[2-(3-methyl-2-thienyl)ethenyl]-,(4R)-(9CI) Structure

2-Oxazolidinone...

(2S)-tert-butoxycarbonylamino-3-n-hexanoyloxy-2-methyl-1-propanal Structure

(2S)-tert-butox...

~%

(4R)-4-[2-(3-chlorothiophen-2-yl)ethenyl]-4-methyl-1,3-oxazolidin-2-one Structure

(4R)-4-[2-(3-ch...

(2R)-tert-butoxycarbonylamino-3-n-hexanoyloxy-2-methyl-1-propanol Structure

(2R)-tert-butox...

~%

(4R)-4-[2-(3-chlorothiophen-2-yl)ethenyl]-4-methyl-1,3-oxazolidin-2-one Structure

(4R)-4-[2-(3-ch...

Carbamic acid, [2-hydroxy-1-(hydroxymethyl)-1-methylethyl]-, 1,1-dimethylethyl Structure

Carbamic acid, ...

~%

(4R)-4-[2-(3-chlorothiophen-2-yl)ethenyl]-4-methyl-1,3-oxazolidin-2-one Structure

(4R)-4-[2-(3-ch...