(1R,6S,7R,8S,10S,11R,12S)-10-acetoxymethyl-11-benzyloxy-6-methyl-13-oxa-2,4,8-triazatetracyclo[8.2.1.0^2,7.0^8,12]tridecan-3,5-dione

Base Information

• Chemical Name: (1R,6S,7R,8S,10S,11R,12S)-10-acetoxymethyl-11-benzyloxy-6-methyl-13-oxa-2,4,8-triazatetracyclo[8.2.1.0^2,7.0^8,12]tridecan-3,5-dione
• CAS No.: 894430-50-3
• Molecular Formula: C₂₀H₂₃N₃O₆
• Molecular Weight: 401.419

Synonyms:(1R,6S,7R,8S,10S,11R,12S)-10-acetoxymethyl-11-benzyloxy-6-methyl-13-oxa-2,4,8-triazatetracyclo[8.2.1.0^2,7.0^8,12]tridecan-3,5-dione

Chemical Property of (1R,6S,7R,8S,10S,11R,12S)-10-acetoxymethyl-11-benzyloxy-6-methyl-13-oxa-2,4,8-triazatetracyclo[8.2.1.0^2,7.0^8,12]tridecan-3,5-dione

Chemical Property:

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Technology Process of (1R,6S,7R,8S,10S,11R,12S)-10-acetoxymethyl-11-benzyloxy-6-methyl-13-oxa-2,4,8-triazatetracyclo[8.2.1.0^2,7.0^8,12]tridecan-3,5-dione

There total 2 articles about (1R,6S,7R,8S,10S,11R,12S)-10-acetoxymethyl-11-benzyloxy-6-methyl-13-oxa-2,4,8-triazatetracyclo[8.2.1.0^2,7.0^8,12]tridecan-3,5-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: 32.0%

(1S,3R,4S,7R)-7-benzyloxy-1-methanesulfonoxymethyl-3-(thymin-1-yl)-2-oxa-5-azabicyclo[2.2.1]heptane (894430-43-4) + potassium acetate (127-08-2) → (1S,3R,4S,7R)-1-acetyloxymethyl-7-benzyloxy-3-(thymin-1-yl)-2-oxa-5-aza-bicyclo[2.2.1]heptane + (1R,6R,7S,8S,10S,11R,12S)-10-acetoxymethyl-11-benzyloxy-6-methyl-13-oxa-2,4,8-triazatetracyclo[8.2.1.02,7.08,12]tridecan-3,5-dione (894430-51-4) + (1R,6S,7R,8S,10S,11R,12S)-10-acetoxymethyl-11-benzyloxy-6-methyl-13-oxa-2,4,8-triazatetracyclo[8.2.1.02,7.08,12]tridecan-3,5-dione (894430-50-3)

Guidance literature:

With 18-crown-6 ether; In 1,4-dioxane; Heating;

DOI:10.1021/jo060331f

Reference yield:

1-[2-azido-3-O-benzyl-2-deoxy-5-O-methanesulfonyl-4-C-methanesulfonoxymethyl-L-erythro-pentofuranosyl]thymine → (1R,6S,7R,8S,10S,11R,12S)-10-acetoxymethyl-11-benzyloxy-6-methyl-13-oxa-2,4,8-triazatetracyclo[8.2.1.02,7.08,12]tridecan-3,5-dione (894430-50-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 4.11 g / aq. NaOH; PMe₃ / tetrahydrofuran / 20 h / 20 °C

2: 18 percent / 18-crown-6 / dioxane / Heating

With sodium hydroxide; 18-crown-6 ether; trimethylphosphane; In tetrahydrofuran; 1,4-dioxane; 1: Staudinger reaction;

DOI:10.1021/jo060331f

Reference yield:

(1R,6S,7R,8S,10S,11R,12S)-10-acetoxymethyl-11-benzyloxy-6-methyl-13-oxa-2,4,8-triazatetracyclo[8.2.1.02,7.08,12]tridecan-3,5-dione (894430-50-3) → C18H21N3O5

Guidance literature:

With ammonia; In methanol; at 20 ℃; for 14h;

DOI:10.1021/jo060331f

upstream raw materials:

(1S,3R,4S,7R)-7-benzyloxy-1-methanesulfonoxymethyl-3-(thymin-1-yl)-2-oxa-5-azabicyclo[2.2.1]heptane

potassium acetate

Downstream raw materials:

(1R,6S,7R,8S,10S,11R,12S)-10-(4,4'-dimethoxytrityloxymethyl)-11-hydroxy-6-methyl-13-oxa-2,4,8-triazatetracyclo[8.2.1.0^2,7.0^8,12]tridecan-3,5-dione

(1R,6S,7R,8S,10S,11R,12S)-11-benzyloxy-10-(4,4'-dimethoxytrityloxymethyl)-6-methyl-13-oxa-2,4,8-triazatetracyclo[8.2.1.0^2,7.0^8,12]tridecan-3,5-dione

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