N-<(1S,3S,6R,7S,8S,10S)-7,10-bis(benzyloxy)-4-oxo-2,9-dioxatricyclo<4.3.1.0^3,8>dec-6-yl>acetamide

Base Information

• Chemical Name: N-<(1S,3S,6R,7S,8S,10S)-7,10-bis(benzyloxy)-4-oxo-2,9-dioxatricyclo<4.3.1.0^3,8>dec-6-yl>acetamide
• CAS No.: 158605-50-6
• Molecular Formula: C₂₄H₂₅NO₆
• Molecular Weight: 423.466

Synonyms:N-<(1S,3S,6R,7S,8S,10S)-7,10-bis(benzyloxy)-4-oxo-2,9-dioxatricyclo<4.3.1.0^3,8>dec-6-yl>acetamide

Chemical Property of N-<(1S,3S,6R,7S,8S,10S)-7,10-bis(benzyloxy)-4-oxo-2,9-dioxatricyclo<4.3.1.0^3,8>dec-6-yl>acetamide

Chemical Property:

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Technology Process of N-<(1S,3S,6R,7S,8S,10S)-7,10-bis(benzyloxy)-4-oxo-2,9-dioxatricyclo<4.3.1.0^3,8>dec-6-yl>acetamide

There total 2 articles about N-<(1S,3S,6R,7S,8S,10S)-7,10-bis(benzyloxy)-4-oxo-2,9-dioxatricyclo<4.3.1.0^3,8>dec-6-yl>acetamide 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:

Acetic acid (1S,3S,6R,7S,8S,10S)-10-acetoxy-6-acetylamino-4-oxo-2,9-dioxa-tricyclo[4.3.1.03,8]dec-7-yl ester (144152-64-7) → N-<(1S,3S,6R,7S,8S,10S)-7,10-bis(benzyloxy)-4-oxo-2,9-dioxatricyclo<4.3.1.03,8>dec-6-yl>acetamide (158605-50-6)

Guidance literature:

Multi-step reaction with 2 steps

1: NaH / methanol; paraffin / 0.25 h

2: NaH, TBAI / tetrahydrofuran; dimethylformamide; paraffin / 24 h

With tetra-(n-butyl)ammonium iodide; sodium hydride; In tetrahydrofuran; methanol; N,N-dimethyl-formamide; paraffin;

DOI:10.1021/jo951747o

Reference yield:

benzyl bromide (100-39-0) + N-((1S,3S,6R,7S,8S,10S)-7,10-Dihydroxy-4-oxo-2,9-dioxa-tricyclo[4.3.1.03,8]dec-6-yl)-acetamide → N-<(1S,3S,6R,7S,8S,10S)-7,10-bis(benzyloxy)-4-oxo-2,9-dioxatricyclo<4.3.1.03,8>dec-6-yl>acetamide (158605-50-6)

Guidance literature:

With tetra-(n-butyl)ammonium iodide; sodium hydride; In tetrahydrofuran; N,N-dimethyl-formamide; paraffin; for 24h; Yield given;

DOI:10.1021/jo951747o

Reference yield: 79.0%

methyl-triphenylphosphonium iodide (2065-66-9) + N-<(1S,3S,6R,7S,8S,10S)-7,10-bis(benzyloxy)-4-oxo-2,9-dioxatricyclo<4.3.1.03,8>dec-6-yl>acetamide (158605-50-6) → N-<7,10-bis(benzyloxy)-4-methylene-2,9-dioxatricyclo<4.3.1.03,8>dec-6-yl>acetamide (158605-52-8)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; 1.) room temperature, 1 h, 2.) 10 h;

DOI:10.1021/jo951747o

upstream raw materials:

benzyl bromide

Acetic acid (1S,3S,6R,7S,8S,10S)-10-acetoxy-6-acetylamino-4-oxo-2,9-dioxa-tricyclo[4.3.1.0^3,8]dec-7-yl ester

Downstream raw materials:

N-<7,10-bis(benzyloxy)-4-methylene-2,9-dioxatricyclo<4.3.1.0^3,8>dec-6-yl>acetamide

N-((1R,3S,4S,5R,9S)-4,9-Bis-benzyloxy-7-formyl-3-hydroxy-2-oxa-bicyclo[3.3.1]non-7-en-5-yl)-acetamide

N-[(1R,3S,4S,5R,8S,9S)-4,9-Bis-benzyloxy-8-hydroxy-3-(4-methoxy-benzyloxy)-7-methylene-2-oxa-bicyclo[3.3.1]non-5-yl]-acetamide

N-[(1R,3S,4S,5R,9S)-4,9-Bis-benzyloxy-7-formyl-3-(4-methoxy-benzyloxy)-2-oxa-bicyclo[3.3.1]non-7-en-5-yl]-acetamide

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