(1R,6R,7S,8R,9R,10R,15R,16S,17R,18R)-8,17-Bis-benzyloxy-7,9,16,18-tetrakis-methoxymethoxy-19,20-dioxa-3,12-diaza-tricyclo[13.3.1.1^6,10]icosane-4,13-dione

Base Information

• Chemical Name: (1R,6R,7S,8R,9R,10R,15R,16S,17R,18R)-8,17-Bis-benzyloxy-7,9,16,18-tetrakis-methoxymethoxy-19,20-dioxa-3,12-diaza-tricyclo[13.3.1.1^6,10]icosane-4,13-dione
• CAS No.: 854377-13-2
• Molecular Formula: C₃₈H₅₄N₂O₁₄
• Molecular Weight: 762.852

Synonyms:(1R,6R,7S,8R,9R,10R,15R,16S,17R,18R)-8,17-Bis-benzyloxy-7,9,16,18-tetrakis-methoxymethoxy-19,20-dioxa-3,12-diaza-tricyclo[13.3.1.1^6,10]icosane-4,13-dione

Chemical Property of (1R,6R,7S,8R,9R,10R,15R,16S,17R,18R)-8,17-Bis-benzyloxy-7,9,16,18-tetrakis-methoxymethoxy-19,20-dioxa-3,12-diaza-tricyclo[13.3.1.1^6,10]icosane-4,13-dione

Chemical Property:

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MSDS Files:

Useful:

Technology Process of (1R,6R,7S,8R,9R,10R,15R,16S,17R,18R)-8,17-Bis-benzyloxy-7,9,16,18-tetrakis-methoxymethoxy-19,20-dioxa-3,12-diaza-tricyclo[13.3.1.1^6,10]icosane-4,13-dione

There total 6 articles about (1R,6R,7S,8R,9R,10R,15R,16S,17R,18R)-8,17-Bis-benzyloxy-7,9,16,18-tetrakis-methoxymethoxy-19,20-dioxa-3,12-diaza-tricyclo[13.3.1.1^6,10]icosane-4,13-dione 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:

(6'-azido-3'-O-benzyl-6'-deoxy-2',4'-di-O-methoxymethyl-α-D-glucopyranosyl)ethanoic acid (854377-20-1) → (1R,6R,7S,8R,9R,10R,15R,16S,17R,18R)-8,17-Bis-benzyloxy-7,9,16,18-tetrakis-methoxymethoxy-19,20-dioxa-3,12-diaza-tricyclo[13.3.1.16,10]icosane-4,13-dione (854377-13-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 83 percent / diethyl phosphoryl cyanide; Et₃N / dimethylformamide / 20 °C

2: 93 percent / LiOH / tetrahydrofuran; methanol; H₂O / 20 °C

3: H₂ / Pd/C / methanol

4: 400 mg / diethyl phosphoryl cyanide; Et₃N / dimethylformamide / 20 °C

With lithium hydroxide; diethyl cyanophosphonate; hydrogen; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; water; N,N-dimethyl-formamide;

DOI:10.1021/jo0502899

Reference yield:

((2R,3S,4R,5R,6R)-6-{[2-((2R,3S,4R,5R,6R)-6-Aminomethyl-4-benzyloxy-3,5-bis-methoxymethoxy-tetrahydro-pyran-2-yl)-acetylamino]-methyl}-4-benzyloxy-3,5-bis-methoxymethoxy-tetrahydro-pyran-2-yl)-acetic acid → (1R,6R,7S,8R,9R,10R,15R,16S,17R,18R)-8,17-Bis-benzyloxy-7,9,16,18-tetrakis-methoxymethoxy-19,20-dioxa-3,12-diaza-tricyclo[13.3.1.16,10]icosane-4,13-dione (854377-13-2)

Guidance literature:

With diethyl cyanophosphonate; triethylamine; In N,N-dimethyl-formamide; at 20 ℃;

DOI:10.1021/jo0502899

Reference yield:

methyl (6'-amino-3'-O-benzyl-6'-deoxy-2',4'-di-O-methoxymethyl-α-D-glucopyranosyl)ethanoate (854377-24-5) → (1R,6R,7S,8R,9R,10R,15R,16S,17R,18R)-8,17-Bis-benzyloxy-7,9,16,18-tetrakis-methoxymethoxy-19,20-dioxa-3,12-diaza-tricyclo[13.3.1.16,10]icosane-4,13-dione (854377-13-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 83 percent / diethyl phosphoryl cyanide; Et₃N / dimethylformamide / 20 °C

2: 93 percent / LiOH / tetrahydrofuran; methanol; H₂O / 20 °C

3: H₂ / Pd/C / methanol

4: 400 mg / diethyl phosphoryl cyanide; Et₃N / dimethylformamide / 20 °C

With lithium hydroxide; diethyl cyanophosphonate; hydrogen; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; water; N,N-dimethyl-formamide;

DOI:10.1021/jo0502899

upstream raw materials:

methyl (6'-amino-3'-O-benzyl-6'-deoxy-2',4'-di-O-methoxymethyl-α-D-glucopyranosyl)ethanoate

(6'-azido-3'-O-benzyl-6'-deoxy-2',4'-di-O-methoxymethyl-α-D-glucopyranosyl)ethanoic acid

methyl (6'-azido-3'-O-benzyl-6'-deoxy-2',4'-di-O-methoxymethyl-α-D-glucopyranosyl)ethanoate

((2R,3S,4R,5R,6R)-6-{[2-((2R,3S,4R,5R,6R)-6-Azidomethyl-4-benzyloxy-3,5-bis-methoxymethoxy-tetrahydro-pyran-2-yl)-acetylamino]-methyl}-4-benzyloxy-3,5-bis-methoxymethoxy-tetrahydro-pyran-2-yl)-acetic acid

Downstream raw materials:

(1R,6R,7S,8R,9R,10R,15R,16S,17R,18R)-8,17-Bis-benzyloxy-7,9,16,18-tetrahydroxy-19,20-dioxa-3,12-diaza-tricyclo[13.3.1.1^6,10]icosane-4,13-dione

(1R,6R,7S,8R,9R,10R,15R,16S,17R,18R)-8,17-Bis-benzyloxy-7,9,16,18-tetrakis-methoxymethoxy-19,20-dioxa-3,12-diaza-tricyclo[13.3.1.1^6,10]icosane

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