(5R,6S,7S)-N-methyl,N-methoxy-9-benzyloxy-4,5-dimethyl-5-(triethylsilyl)oxy-2-nonanecarboxamide

Base Information

• Chemical Name: (5R,6S,7S)-N-methyl,N-methoxy-9-benzyloxy-4,5-dimethyl-5-(triethylsilyl)oxy-2-nonanecarboxamide
• CAS No.: 329914-20-7
• Molecular Formula: C₂₆H₄₇NO₄Si
• Molecular Weight: 465.749

Synonyms:(5R,6S,7S)-N-methyl,N-methoxy-9-benzyloxy-4,5-dimethyl-5-(triethylsilyl)oxy-2-nonanecarboxamide

Chemical Property of (5R,6S,7S)-N-methyl,N-methoxy-9-benzyloxy-4,5-dimethyl-5-(triethylsilyl)oxy-2-nonanecarboxamide

Chemical Property:

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Technology Process of (5R,6S,7S)-N-methyl,N-methoxy-9-benzyloxy-4,5-dimethyl-5-(triethylsilyl)oxy-2-nonanecarboxamide

There total 2 articles about (5R,6S,7S)-N-methyl,N-methoxy-9-benzyloxy-4,5-dimethyl-5-(triethylsilyl)oxy-2-nonanecarboxamide 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: 96.0%

(5R,6S,7S)-N-methyl,N-methoxy-9-benzyloxy-4,5-dimethyl-5-(triethylsilyl)oxy-2-nonynecarboxamide (329914-19-4) → (5R,6S,7S)-N-methyl,N-methoxy-9-benzyloxy-4,5-dimethyl-5-(triethylsilyl)oxy-2-nonanecarboxamide (329914-20-7)

Guidance literature:

With hydrogen; Lindlar's catalyst; In ethyl acetate; for 22h;

DOI:10.1021/jo0056951

Reference yield:

C23H37LiO2Si → (5R,6S,7S)-N-methyl,N-methoxy-9-benzyloxy-4,5-dimethyl-5-(triethylsilyl)oxy-2-nonanecarboxamide (329914-20-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 73 percent / tetrahydrofuran / 1 h / -78 - 0 °C

2: 96 percent / H₂ / Pd/CaCO₃/Pb / ethyl acetate / 22 h

With hydrogen; Lindlar's catalyst; In tetrahydrofuran; ethyl acetate;

DOI:10.1021/jo0056951

Reference yield: 88.0%

C16H32SiO2SiC6H13Li + (5R,6S,7S)-N-methyl,N-methoxy-9-benzyloxy-4,5-dimethyl-5-(triethylsilyl)oxy-2-nonanecarboxamide (329914-20-7) → (2S,5S,6R,12S,13S,14R)-17-Benzyloxy-1-(tert-butyl-dimethyl-silanyloxy)-2,6,12,14-tetramethyl-5,13-bis-triethylsilanyloxy-heptadec-7-yn-9-one (329914-21-8)

Guidance literature:

In tetrahydrofuran; at -78 - 0 ℃; for 1h;

DOI:10.1021/jo0056951

upstream raw materials:

(5R,6S,7S)-N-methyl,N-methoxy-9-benzyloxy-4,5-dimethyl-5-(triethylsilyl)oxy-2-nonynecarboxamide

Downstream raw materials:

(2S,5S,6R,12S,13S,14R)-17-Benzyloxy-1-(tert-butyl-dimethyl-silanyloxy)-2,6,12,14-tetramethyl-5,13-bis-triethylsilanyloxy-heptadec-7-yn-9-one

(S)-4-[(2S,3R,6R,8S,9S)-8-((R)-4-Benzyloxy-1-methyl-butyl)-3,9-dimethyl-1,7-dioxa-spiro[5.5]undec-2-yl]-2-methyl-butyraldehyde

(2S,3S,6R,8S,9R)-2-((R)-4-Benzyloxy-1-methyl-butyl)-3,9-dimethyl-8-((S)-3-methyl-pent-4-enyl)-1,7-dioxa-spiro[5.5]undecane

(S)-4-[(2S,3R,6R,8S,9S)-8-((R)-4-Benzyloxy-1-methyl-butyl)-3,9-dimethyl-1,7-dioxa-spiro[5.5]undec-2-yl]-2-methyl-butan-1-ol

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