(1R,6R,7S,8R,9R,10R,15R,16S,17R,18R)-8,17-Bis-benzyloxy-7,9,16,18-tetramethoxy-19,20-dioxa-3,12-diaza-tricyclo[13.3.1.1^6,10]icosane-3,12-dicarboxylic acid di-tert-butyl ester

Base Information

• Chemical Name: (1R,6R,7S,8R,9R,10R,15R,16S,17R,18R)-8,17-Bis-benzyloxy-7,9,16,18-tetramethoxy-19,20-dioxa-3,12-diaza-tricyclo[13.3.1.1^6,10]icosane-3,12-dicarboxylic acid di-tert-butyl ester
• CAS No.: 886552-61-0
• Molecular Formula: C₄₄H₆₆N₂O₁₂
• Molecular Weight: 815.014

Synonyms:(1R,6R,7S,8R,9R,10R,15R,16S,17R,18R)-8,17-Bis-benzyloxy-7,9,16,18-tetramethoxy-19,20-dioxa-3,12-diaza-tricyclo[13.3.1.1^6,10]icosane-3,12-dicarboxylic acid di-tert-butyl ester

Chemical Property of (1R,6R,7S,8R,9R,10R,15R,16S,17R,18R)-8,17-Bis-benzyloxy-7,9,16,18-tetramethoxy-19,20-dioxa-3,12-diaza-tricyclo[13.3.1.1^6,10]icosane-3,12-dicarboxylic acid di-tert-butyl ester

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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-tetramethoxy-19,20-dioxa-3,12-diaza-tricyclo[13.3.1.1^6,10]icosane-3,12-dicarboxylic acid di-tert-butyl ester

There total 4 articles about (1R,6R,7S,8R,9R,10R,15R,16S,17R,18R)-8,17-Bis-benzyloxy-7,9,16,18-tetramethoxy-19,20-dioxa-3,12-diaza-tricyclo[13.3.1.1^6,10]icosane-3,12-dicarboxylic acid di-tert-butyl ester 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: 97.0%

(1R,6R,7S,8R,9R,10R,15R,16S,17R,18R)-8,17-Bis-benzyloxy-7,9,16,18-tetramethoxy-19,20-dioxa-3,12-diaza-tricyclo[13.3.1.16,10]icosane (886552-45-0) + di-tert-butyl dicarbonate (24424-99-5) → (1R,6R,7S,8R,9R,10R,15R,16S,17R,18R)-8,17-Bis-benzyloxy-7,9,16,18-tetramethoxy-19,20-dioxa-3,12-diaza-tricyclo[13.3.1.16,10]icosane-3,12-dicarboxylic acid di-tert-butyl ester (886552-61-0)

Guidance literature:

With triethylamine; In dichloromethane; at 20 ℃; for 2h;

DOI:10.1021/jo052489q

Reference yield:

(6'-azido-3'-O-benzyl-6'-deoxy-2',4'-di-O-methyl-α-D-glucopyranosyl)-acetaldehyde (886552-41-6) → (1R,6R,7S,8R,9R,10R,15R,16S,17R,18R)-8,17-Bis-benzyloxy-7,9,16,18-tetramethoxy-19,20-dioxa-3,12-diaza-tricyclo[13.3.1.16,10]icosane-3,12-dicarboxylic acid di-tert-butyl ester (886552-61-0)

Guidance literature:

Multi-step reaction with 3 steps

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

2.1: NaBH(OAc)3 / tetrahydrofuran / 20 h / 20 °C

2.2: 69 percent / Pd/C / methanol / 24 h / 20 °C

3.1: 97 percent / Et₃N / CH₂Cl₂ / 2 h / 20 °C

With polymer-bound diphenylphosphine; sodium tris(acetoxy)borohydride; triethylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jo052489q

Reference yield:

(3E,12E)-(1R,6R,7S,8R,9R,10R,15R,16S,17R,18R)-8,17-Bis-benzyloxy-7,9,16,18-tetramethoxy-19,20-dioxa-3,12-diaza-tricyclo[13.3.1.16,10]icosa-3,12-diene (886552-43-8) → (1R,6R,7S,8R,9R,10R,15R,16S,17R,18R)-8,17-Bis-benzyloxy-7,9,16,18-tetramethoxy-19,20-dioxa-3,12-diaza-tricyclo[13.3.1.16,10]icosane-3,12-dicarboxylic acid di-tert-butyl ester (886552-61-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: NaBH(OAc)3 / tetrahydrofuran / 20 h / 20 °C

1.2: 69 percent / Pd/C / methanol / 24 h / 20 °C

2.1: 97 percent / Et₃N / CH₂Cl₂ / 2 h / 20 °C

With sodium tris(acetoxy)borohydride; triethylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jo052489q

upstream raw materials:

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

di-tert-butyl dicarbonate

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

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

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