[(S)-2-(1H-Indol-3-yl)-1-(4-methyl-2,6,7-trioxa-bicyclo[2.2.2]oct-1-yl)-ethyl]-carbamic acid benzyl ester

Base Information

• Chemical Name: [(S)-2-(1H-Indol-3-yl)-1-(4-methyl-2,6,7-trioxa-bicyclo[2.2.2]oct-1-yl)-ethyl]-carbamic acid benzyl ester
• CAS No.: 127130-94-3
• Molecular Formula: C₂₄H₂₆N₂O₅
• Molecular Weight: 422.481

Synonyms:[(S)-2-(1H-Indol-3-yl)-1-(4-methyl-2,6,7-trioxa-bicyclo[2.2.2]oct-1-yl)-ethyl]-carbamic acid benzyl ester

Chemical Property of [(S)-2-(1H-Indol-3-yl)-1-(4-methyl-2,6,7-trioxa-bicyclo[2.2.2]oct-1-yl)-ethyl]-carbamic acid benzyl ester

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Technology Process of [(S)-2-(1H-Indol-3-yl)-1-(4-methyl-2,6,7-trioxa-bicyclo[2.2.2]oct-1-yl)-ethyl]-carbamic acid benzyl ester

There total 3 articles about [(S)-2-(1H-Indol-3-yl)-1-(4-methyl-2,6,7-trioxa-bicyclo[2.2.2]oct-1-yl)-ethyl]-carbamic acid benzyl 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: 84.0%

N-(benzyloxycarbonyl)-L-tryptophane (3-methyl-3-oxetanyl)methyl ester (127130-93-2) → [(S)-2-(1H-Indol-3-yl)-1-(4-methyl-2,6,7-trioxa-bicyclo[2.2.2]oct-1-yl)-ethyl]-carbamic acid benzyl ester (127130-94-3)

Guidance literature:

With boron trifluoride; In diethyl ether; dichloromethane; at -4 ℃; for 2h;

DOI:10.1021/ja00180a049

Reference yield:

3-hydroxymethyl-3-methyloxethane (3143-02-0) → [(S)-2-(1H-Indol-3-yl)-1-(4-methyl-2,6,7-trioxa-bicyclo[2.2.2]oct-1-yl)-ethyl]-carbamic acid benzyl ester (127130-94-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 84 percent / (dimethylamino)pyridine, dicylohexylcarbodiimide / diethyl ether / 0.25 h / 25 °C

2: 84 percent / BF₃ / CH₂Cl₂; diethyl ether / 2 h / -4 °C

With dmap; boron trifluoride; dicyclohexyl-carbodiimide; In diethyl ether; dichloromethane;

DOI:10.1021/ja00180a049

Reference yield:

N-carbobenzyloxy-L-tryptophane (7432-21-5) → [(S)-2-(1H-Indol-3-yl)-1-(4-methyl-2,6,7-trioxa-bicyclo[2.2.2]oct-1-yl)-ethyl]-carbamic acid benzyl ester (127130-94-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 84 percent / (dimethylamino)pyridine, dicylohexylcarbodiimide / diethyl ether / 0.25 h / 25 °C

2: 84 percent / BF₃ / CH₂Cl₂; diethyl ether / 2 h / -4 °C

With dmap; boron trifluoride; dicyclohexyl-carbodiimide; In diethyl ether; dichloromethane;

DOI:10.1021/ja00180a049

upstream raw materials:

N-(benzyloxycarbonyl)-L-tryptophane (3-methyl-3-oxetanyl)methyl ester

3-hydroxymethyl-3-methyloxethane

N-carbobenzyloxy-L-tryptophane

Downstream raw materials:

(2S,3aS,6aS,11bS)-3-(tert-Butyl-dimethyl-silanyl)-2-(4-methyl-2,6,7-trioxa-bicyclo[2.2.2]oct-1-yl)-5-oxo-1,2,3,3a,4,5,6,6a-octahydro-pyrrolo[2,3-d]carbazole-7-carboxylic acid benzyl ester

(2S,3'S,5'S)-5'-(4-Methyl-2,6,7-trioxa-bicyclo[2.2.2]oct-1-yl)-2-(2-oxo-propyl)-4',5'-dihydro-spiro[indole-3,3'-pyrrole]-1-carboxylic acid benzyl ester

3-[(S)-2-(4-Methyl-2,6,7-trioxa-bicyclo[2.2.2]oct-1-yl)-2-((Z)-3-oxo-but-1-enylamino)-ethyl]-indole-1-carboxylic acid benzyl ester

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