2-((1R,2R,3S,6S,7R,9R)-1-Benzyloxymethyl-2-bromo-5-oxo-4,8-dioxa-tricyclo[4.2.1.0^3,7]non-9-yl)-N-[2-(6-methoxy-1H-indol-3-yl)-ethyl]-acetamide

Base Information

• Chemical Name: 2-((1R,2R,3S,6S,7R,9R)-1-Benzyloxymethyl-2-bromo-5-oxo-4,8-dioxa-tricyclo[4.2.1.0^3,7]non-9-yl)-N-[2-(6-methoxy-1H-indol-3-yl)-ethyl]-acetamide
• CAS No.: 74207-01-5
• Molecular Formula: C₂₈H₂₉BrN₂O₆
• Molecular Weight: 569.452
• Mol file: 74207-01-5.mol

Synonyms:

Chemical Property of 2-((1R,2R,3S,6S,7R,9R)-1-Benzyloxymethyl-2-bromo-5-oxo-4,8-dioxa-tricyclo[4.2.1.0^3,7]non-9-yl)-N-[2-(6-methoxy-1H-indol-3-yl)-ethyl]-acetamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-((1R,2R,3S,6S,7R,9R)-1-Benzyloxymethyl-2-bromo-5-oxo-4,8-dioxa-tricyclo[4.2.1.0^3,7]non-9-yl)-N-[2-(6-methoxy-1H-indol-3-yl)-ethyl]-acetamide

There total 5 articles about 2-((1R,2R,3S,6S,7R,9R)-1-Benzyloxymethyl-2-bromo-5-oxo-4,8-dioxa-tricyclo[4.2.1.0^3,7]non-9-yl)-N-[2-(6-methoxy-1H-indol-3-yl)-ethyl]-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: 65.0%

2-diazoaceto-3-benzyloxymethyl-4-bromo-3,8-epoxy-7-oxo-6-oxabicyclo<3.2.1>octane + 2-(6-methoxy-1H-indol-3-yl)ethanamine (3610-36-4) → 2-((1R,2R,3S,6S,7R,9R)-1-Benzyloxymethyl-2-bromo-5-oxo-4,8-dioxa-tricyclo[4.2.1.03,7]non-9-yl)-N-[2-(6-methoxy-1H-indol-3-yl)-ethyl]-acetamide (74207-01-5)

Guidance literature:

With silver(l) oxide; In 1,4-dioxane; for 3h; Heating;

DOI:10.1248/cpb.29.76

Reference yield:

2-benzyloxymethylfuran (16361-14-1) → 2-((1R,2R,3S,6S,7R,9R)-1-Benzyloxymethyl-2-bromo-5-oxo-4,8-dioxa-tricyclo[4.2.1.03,7]non-9-yl)-N-[2-(6-methoxy-1H-indol-3-yl)-ethyl]-acetamide (74207-01-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) hydroquinone; 2.) NaHCO₃, bromine / 1.) water, r.t., 7 d; 2.) water, r.t., 2 h

2: oxalyl chloride / benzene / 4 h / Heating

3: diethyl ether / 17 h

4: 65 percent / silver oxide / dioxane / 3 h / Heating

With oxalyl dichloride; bromine; sodium hydrogencarbonate; hydroquinone; silver(l) oxide; In 1,4-dioxane; diethyl ether; benzene;

DOI:10.1248/cpb.29.76

Reference yield:

(1R,2R,3S,6S,7R,9R)-1-Benzyloxymethyl-2-bromo-5-oxo-4,8-dioxa-tricyclo[4.2.1.03,7]nonane-9-carbonyl chloride (74206-98-7) → 2-((1R,2R,3S,6S,7R,9R)-1-Benzyloxymethyl-2-bromo-5-oxo-4,8-dioxa-tricyclo[4.2.1.03,7]non-9-yl)-N-[2-(6-methoxy-1H-indol-3-yl)-ethyl]-acetamide (74207-01-5)

Guidance literature:

Multi-step reaction with 2 steps

1: diethyl ether / 17 h

2: 65 percent / silver oxide / dioxane / 3 h / Heating

With silver(l) oxide; In 1,4-dioxane; diethyl ether;

DOI:10.1248/cpb.29.76

upstream raw materials:

2-(6-methoxy-1H-indol-3-yl)ethanamine

2-benzyloxymethylfuran

3-benzyloxymethyl-4-bromo-3,8-epoxy-7-oxo-6-oxabicyclo<3.2.1>octane-2-carboxylic acid

(1R,2R,3S,6S,7R,9R)-1-Benzyloxymethyl-2-bromo-5-oxo-4,8-dioxa-tricyclo[4.2.1.0^3,7]nonane-9-carbonyl chloride