(E)-(2R,3R,4R,5R)-4,5-Bis-benzyloxy-3-hydroxy-2-methoxy-8-methyl-non-6-enoic acid ((S)-2-oxo-azepan-3-yl)-amide

Base Information

Chemical Name:(E)-(2R,3R,4R,5R)-4,5-Bis-benzyloxy-3-hydroxy-2-methoxy-8-methyl-non-6-enoic acid ((S)-2-oxo-azepan-3-yl)-amide
CAS No.:430473-73-7
Molecular Formula:C₃₁H₄₂N₂O₆
Molecular Weight:538.684
Hs Code.:

Synonyms:(E)-(2R,3R,4R,5R)-4,5-Bis-benzyloxy-3-hydroxy-2-methoxy-8-methyl-non-6-enoic acid ((S)-2-oxo-azepan-3-yl)-amide

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Chemical Property of (E)-(2R,3R,4R,5R)-4,5-Bis-benzyloxy-3-hydroxy-2-methoxy-8-methyl-non-6-enoic acid ((S)-2-oxo-azepan-3-yl)-amide

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Technology Process of (E)-(2R,3R,4R,5R)-4,5-Bis-benzyloxy-3-hydroxy-2-methoxy-8-methyl-non-6-enoic acid ((S)-2-oxo-azepan-3-yl)-amide

There total 9 articles about (E)-(2R,3R,4R,5R)-4,5-Bis-benzyloxy-3-hydroxy-2-methoxy-8-methyl-non-6-enoic acid ((S)-2-oxo-azepan-3-yl)-amide 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: 87.0%

: 26081-03-8,26081-07-2,29110-16-5,29426-64-0,40862-36-0,99560-25-5
(S)-3-aminocaprolactam hydrochloride

: 430473-72-6
(E)-(2R,3R,4R,5R)-4,5-Bis-benzyloxy-3-hydroxy-2-methoxy-8-methyl-non-6-enethioic acid S-phenyl ester

: 430473-73-7
(E)-(2R,3R,4R,5R)-4,5-Bis-benzyloxy-3-hydroxy-2-methoxy-8-methyl-non-6-enoic acid ((S)-2-oxo-azepan-3-yl)-amide

Guidance literature:: With sodium 2-ethylhexanoic acid; In tetrahydrofuran;
DOI:10.1016/S0040-4039(02)00022-9

Reference yield:

: 100-39-0
benzyl bromide

: 430473-73-7
(E)-(2R,3R,4R,5R)-4,5-Bis-benzyloxy-3-hydroxy-2-methoxy-8-methyl-non-6-enoic acid ((S)-2-oxo-azepan-3-yl)-amide

Guidance literature:: Multi-step reaction with 9 steps

1: 60 percent / NaH; nBu₄NI / tetrahydrofuran / 20 °C

2: 86 percent / LAH / tetrahydrofuran / 20 °C

3: 92 percent / NaH; nBu₄NI / tetrahydrofuran

4: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

5: LHMDS / tetrahydrofuran / 1 h / -78 - 20 °C

6: 83 percent / TBAF / tetrahydrofuran / 0 °C

7: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

8: EtNMe₂; LiI; TiCl₄ / CH₂Cl₂ / -78 °C

9: 87 percent / sodium 2-ethylhexanoate / tetrahydrofuran

With lithium aluminium tetrahydride; oxalyl dichloride; N,N-dimethyl-ethanamine; tetrabutyl ammonium fluoride; titanium tetrachloride; tetra-(n-butyl)ammonium iodide; sodium hydride; dimethyl sulfoxide; triethylamine; lithium iodide; lithium hexamethyldisilazane; sodium 2-ethylhexanoic acid; In tetrahydrofuran; dichloromethane; 5: Julia olefination;
DOI:10.1016/S0040-4039(02)00022-9

Reference yield:

: 113350-84-8
(2R,3R)-(-)-2,3-bis(phenylmethoxy)-1,4-butanediol

: 430473-73-7
(E)-(2R,3R,4R,5R)-4,5-Bis-benzyloxy-3-hydroxy-2-methoxy-8-methyl-non-6-enoic acid ((S)-2-oxo-azepan-3-yl)-amide

Guidance literature:: Multi-step reaction with 7 steps

1: 92 percent / NaH; nBu₄NI / tetrahydrofuran

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

3: LHMDS / tetrahydrofuran / 1 h / -78 - 20 °C

4: 83 percent / TBAF / tetrahydrofuran / 0 °C

5: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

6: EtNMe₂; LiI; TiCl₄ / CH₂Cl₂ / -78 °C

7: 87 percent / sodium 2-ethylhexanoate / tetrahydrofuran

With oxalyl dichloride; N,N-dimethyl-ethanamine; tetrabutyl ammonium fluoride; titanium tetrachloride; tetra-(n-butyl)ammonium iodide; sodium hydride; dimethyl sulfoxide; triethylamine; lithium iodide; lithium hexamethyldisilazane; sodium 2-ethylhexanoic acid; In tetrahydrofuran; dichloromethane; 3: Julia olefination;
DOI:10.1016/S0040-4039(02)00022-9