(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

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
• CAS No.: 854377-16-5
• Molecular Formula: C₃₈H₅₈N₂O₁₂
• Molecular Weight: 734.885

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

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

Chemical Property:

Purity/Quality:

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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

There total 10 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 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: 91.0%

(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) → (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 (854377-16-5)

Guidance literature:

With borane-THF; In tetrahydrofuran; at 66 ℃;

DOI:10.1021/jo0502899

Reference yield: 74.0%

(3E,12E)-(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]icosa-3,12-diene (886552-47-2) → (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 (854377-16-5)

Guidance literature:

(3E,12E)-(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]icosa-3,12-diene; With sodium tris(acetoxy)borohydride; In tetrahydrofuran; at 20 ℃; for 20h;

palladium on activated charcoal; In methanol; at 20 ℃; for 24h;

DOI:10.1021/jo052489q

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 (854377-16-5)

Guidance literature:

Multi-step reaction with 5 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

5: 91 percent / BH₃*THF / tetrahydrofuran / 66 °C

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

DOI:10.1021/jo0502899

upstream raw materials:

(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

(3E,12E)-(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]icosa-3,12-diene

3-(6'-azido-3'-O-benzyl-6'-deoxy-2',4'-di-O-methoxymethyl-α-D-glucopyranosyl)prop-1-ene

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

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