(2R,3R,4R,5R,6E)-5-{[(tert-butyl)dimethylsilyl]oxy}-N-[(3S)-2,3,4,5,6,7-hexahydro-2-oxoazepin-3-yl]-3-hydroxy-2-methoxy-8-methyl-4-[(phenyl)methoxy]non-6-enamide

Base Information

• Chemical Name: (2R,3R,4R,5R,6E)-5-{[(tert-butyl)dimethylsilyl]oxy}-N-[(3S)-2,3,4,5,6,7-hexahydro-2-oxoazepin-3-yl]-3-hydroxy-2-methoxy-8-methyl-4-[(phenyl)methoxy]non-6-enamide
• CAS No.: 442913-29-3
• Molecular Formula: C₃₀H₅₀N₂O₆Si
• Molecular Weight: 562.822
• Mol file: 442913-29-3.mol

Synonyms:(2R,3R,4R,5R,6E)-5-{[(tert-butyl)dimethylsilyl]oxy}-N-[(3S)-2,3,4,5,6,7-hexahydro-2-oxoazepin-3-yl]-3-hydroxy-2-methoxy-8-methyl-4-[(phenyl)methoxy]non-6-enamide

Chemical Property of (2R,3R,4R,5R,6E)-5-{[(tert-butyl)dimethylsilyl]oxy}-N-[(3S)-2,3,4,5,6,7-hexahydro-2-oxoazepin-3-yl]-3-hydroxy-2-methoxy-8-methyl-4-[(phenyl)methoxy]non-6-enamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R,4R,5R,6E)-5-{[(tert-butyl)dimethylsilyl]oxy}-N-[(3S)-2,3,4,5,6,7-hexahydro-2-oxoazepin-3-yl]-3-hydroxy-2-methoxy-8-methyl-4-[(phenyl)methoxy]non-6-enamide

There total 10 articles about (2R,3R,4R,5R,6E)-5-{[(tert-butyl)dimethylsilyl]oxy}-N-[(3S)-2,3,4,5,6,7-hexahydro-2-oxoazepin-3-yl]-3-hydroxy-2-methoxy-8-methyl-4-[(phenyl)methoxy]non-6-enamide 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%

2-aminocaprolactam (21568-87-6) + S-phenyl (4S,5R,6E)-5-tertbutyldimethylsilyloxy-3-hydroxy-2-methoxy-8-methyl-4-phenylmethoxynon-6-enethioate → (2R,3R,4R,5R,6E)-5-{[(tert-butyl)dimethylsilyl]oxy}-N-[(3S)-2,3,4,5,6,7-hexahydro-2-oxoazepin-3-yl]-3-hydroxy-2-methoxy-8-methyl-4-[(phenyl)methoxy]non-6-enamide (442913-29-3)

Guidance literature:

In 1,4-dioxane; for 15h; Heating;

DOI:10.1021/ol026101e

Reference yield: 98.0%

2-aminocaprolactam (21568-87-6) + S-phenyl (2R,3R,4R,5R,6E)-5-{[(tert-butyl)dimethylsilyl]oxy}-3-hydroxy-2-methoxy-8-methyl-4-[(phenyl)methoxy]non-6-enethioate (442913-22-6) → (2R,3R,4R,5R,6E)-5-{[(tert-butyl)dimethylsilyl]oxy}-N-[(3S)-2,3,4,5,6,7-hexahydro-2-oxoazepin-3-yl]-3-hydroxy-2-methoxy-8-methyl-4-[(phenyl)methoxy]non-6-enamide (442913-29-3)

Guidance literature:

In 1,4-dioxane; for 15h; Heating;

DOI:10.1002/hlca.200290026

Reference yield:

(E)-4-methylpent-2-enal (24502-08-7) → (2R,3R,4R,5R,6E)-5-{[(tert-butyl)dimethylsilyl]oxy}-N-[(3S)-2,3,4,5,6,7-hexahydro-2-oxoazepin-3-yl]-3-hydroxy-2-methoxy-8-methyl-4-[(phenyl)methoxy]non-6-enamide (442913-29-3)

Guidance literature:

Multi-step reaction with 6 steps

1.1: DIPEA; diethylboron triflate / CH₂Cl₂ / 1 h / -78 °C

1.2: 85 percent / CH₂Cl₂ / 9 h / -50 °C

2.1: 94 percent / imidazole / dimethylformamide / 13 h / 20 °C

3.1: BiLi / tetrahydrofuran; hexane / 0.33 h / -78 °C

3.2: 93 percent / tetrahydrofuran; hexane / 5 h / -40 °C

4.1: 91 percent / DIBAL / toluene / 0.5 h / -78 °C

5.1: SnCl₄ / heptane; CH₂Cl₂ / 0.5 h / -78 °C

5.2: 73 percent / heptane; CH₂Cl₂ / 4 h / -78 °C

6.1: 98 percent / dioxane / 15 h / Heating

With 1H-imidazole; n-butyllithium; tin(IV) chloride; diisobutylaluminium hydride; N-ethyl-N,N-diisopropylamine; diethylboron trifluoromethanesulfonate; In tetrahydrofuran; 1,4-dioxane; hexane; n-heptane; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1002/hlca.200290026

upstream raw materials:

2-aminocaprolactam

S-phenyl (2R,3R,4R,5R,6E)-5-{[(tert-butyl)dimethylsilyl]oxy}-3-hydroxy-2-methoxy-8-methyl-4-[(phenyl)methoxy]non-6-enethioate

(E)-4-methylpent-2-enal

Benzyloxyacetyl chloride