(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

Base Information

• Chemical Name: (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
• CAS No.: 886552-47-2
• Molecular Formula: C₃₈H₅₄N₂O₁₂
• Molecular Weight: 730.853

Synonyms:(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

Chemical Property of (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

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Technology Process of (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

There total 2 articles about (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 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)-acetaldehyde (886552-37-0) → (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)

Guidance literature:

With polymer-bound diphenylphosphine; In tetrahydrofuran; at 20 ℃; for 20h;

DOI:10.1021/jo052489q

Reference yield:

3-(6'-azido-3'-O-benzyl-6'-deoxy-2',4'-di-O-methoxymethyl-α-D-glucopyranosyl)prop-1-ene (854377-19-8) → (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)

Guidance literature:

Multi-step reaction with 2 steps

1: 65 percent / 2,6-lutidine; OsO₄; NaIO₄ / dioxane; H₂O; 2-methyl-propan-2-ol / 0.5 h / 20 °C

2: polymer-bound diphenylphosphine / tetrahydrofuran / 20 h / 20 °C

With 2,6-dimethylpyridine; sodium periodate; osmium(VIII) oxide; polymer-bound diphenylphosphine; In tetrahydrofuran; 1,4-dioxane; water; tert-butyl alcohol;

DOI:10.1021/jo052489q

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

upstream raw materials:

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

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

Downstream 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

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