(3S,4aS,8aS)-2-[(2R,3S)-3-((S)-2-Azido-2-(S)-tetrahydro-furan-3-yl-acetylamino)-2-hydroxy-4-phenyl-butyl]-decahydro-isoquinoline-3-carboxylic acid tert-butylamide

Base Information

Chemical Name:(3S,4aS,8aS)-2-[(2R,3S)-3-((S)-2-Azido-2-(S)-tetrahydro-furan-3-yl-acetylamino)-2-hydroxy-4-phenyl-butyl]-decahydro-isoquinoline-3-carboxylic acid tert-butylamide
CAS No.:150406-33-0
Molecular Formula:C₃₀H₄₆N₆O₄
Molecular Weight:554.733
Hs Code.:

(3S,4aS,8aS)-2-[(2R,3S)-3-((S)-2-Azido-2-(S)-tetrahydro-furan-3-yl-acetylamino)-2-hydroxy-4-phenyl-butyl]-decahydro-isoquinoline-3-carboxylic acid tert-butylamide

Synonyms:(3S,4aS,8aS)-2-[(2R,3S)-3-((S)-2-Azido-2-(S)-tetrahydro-furan-3-yl-acetylamino)-2-hydroxy-4-phenyl-butyl]-decahydro-isoquinoline-3-carboxylic acid tert-butylamide

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Chemical Property of (3S,4aS,8aS)-2-[(2R,3S)-3-((S)-2-Azido-2-(S)-tetrahydro-furan-3-yl-acetylamino)-2-hydroxy-4-phenyl-butyl]-decahydro-isoquinoline-3-carboxylic acid tert-butylamide

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Technology Process of (3S,4aS,8aS)-2-[(2R,3S)-3-((S)-2-Azido-2-(S)-tetrahydro-furan-3-yl-acetylamino)-2-hydroxy-4-phenyl-butyl]-decahydro-isoquinoline-3-carboxylic acid tert-butylamide

There total 14 articles about (3S,4aS,8aS)-2-[(2R,3S)-3-((S)-2-Azido-2-(S)-tetrahydro-furan-3-yl-acetylamino)-2-hydroxy-4-phenyl-butyl]-decahydro-isoquinoline-3-carboxylic acid tert-butylamide 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:

: 116949-67-8
(2S,3S)-2-azido-1-phenyl-butane-3,4-diol

: 150406-33-0
(3S,4aS,8aS)-2-[(2R,3S)-3-((S)-2-Azido-2-(S)-tetrahydro-furan-3-yl-acetylamino)-2-hydroxy-4-phenyl-butyl]-decahydro-isoquinoline-3-carboxylic acid tert-butylamide

Guidance literature:: Multi-step reaction with 4 steps

1: 1.) 2-acetoxyisobutyryl chloride, 2.) NaOMe / 1.) chloroform, RT, 5 h, 2.) THF, RT, 3 h

2: 9.63 g / propan-2-ol / 80 °C

3: 4.68 g / H₂ / 10percent Pd/C / tetrahydrofuran; methanol; acetic acid / 12 h

4: 0.132 g / 1-hydroxybenzotriazole hydrate, 1-ethyl-3-(3-(dimethylamino)propyl)carbodiimide hydrochloride, 4-methylmorpholine / dimethylformamide / 4 h

With 4-methyl-morpholine; hydrogen; sodium methylate; 2-acetoxy-2-methylpropanoyl chloride; 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; palladium on activated charcoal; In tetrahydrofuran; methanol; acetic acid; N,N-dimethyl-formamide; isopropyl alcohol;
DOI:10.1021/jm00068a006

Reference yield:

: 136465-90-2
N-tert-butyl-2-<2(R)-hydroxy-4-phenyl-3(S)-azidobutyl>decahydro(4aS,8aS)-isoquinoline-3(S)-carboxamide

: 150406-33-0
(3S,4aS,8aS)-2-[(2R,3S)-3-((S)-2-Azido-2-(S)-tetrahydro-furan-3-yl-acetylamino)-2-hydroxy-4-phenyl-butyl]-decahydro-isoquinoline-3-carboxylic acid tert-butylamide

Guidance literature:: Multi-step reaction with 2 steps

1: 4.68 g / H₂ / 10percent Pd/C / tetrahydrofuran; methanol; acetic acid / 12 h

2: 0.132 g / 1-hydroxybenzotriazole hydrate, 1-ethyl-3-(3-(dimethylamino)propyl)carbodiimide hydrochloride, 4-methylmorpholine / dimethylformamide / 4 h

With 4-methyl-morpholine; hydrogen; 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; palladium on activated charcoal; In tetrahydrofuran; methanol; acetic acid; N,N-dimethyl-formamide;
DOI:10.1021/jm00068a006

Reference yield:

: 128019-40-9,149510-73-6,136465-81-1,168899-60-3
(3S,4aS,8aS)-N-tert-butyl-decahydroisoquinoline-3-carboxamide

: 150406-33-0
(3S,4aS,8aS)-2-[(2R,3S)-3-((S)-2-Azido-2-(S)-tetrahydro-furan-3-yl-acetylamino)-2-hydroxy-4-phenyl-butyl]-decahydro-isoquinoline-3-carboxylic acid tert-butylamide

Guidance literature:: Multi-step reaction with 3 steps

1: 1.) AcOCMe₂COCl, 2.) MeONa

2: 100 percent / H₂ / 5percent Pd/C / tetrahydrofuran; methanol; acetic acid / 760 Torr

3: EDC, HOBt, N-methylmorpholine / dimethylformamide

With 4-methyl-morpholine; hydrogen; sodium methylate; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; 2-acetoxy-2-methylpropanoyl chloride; palladium on activated charcoal; In tetrahydrofuran; methanol; acetic acid; N,N-dimethyl-formamide;
DOI:10.1021/ja00055a069