(2S,3S,4R,5R,6S)-2-(5-Azido-pentyloxymethyl)-6-[2-(1-benzenesulfonyl-1H-indol-3-yl)-ethoxy]-4-benzyloxy-5-(1-trityl-1H-imidazol-4-ylmethoxy)-tetrahydro-pyran-3-ol

Base Information

Chemical Name:(2S,3S,4R,5R,6S)-2-(5-Azido-pentyloxymethyl)-6-[2-(1-benzenesulfonyl-1H-indol-3-yl)-ethoxy]-4-benzyloxy-5-(1-trityl-1H-imidazol-4-ylmethoxy)-tetrahydro-pyran-3-ol
CAS No.:543697-13-8
Molecular Formula:C₅₇H₅₈N₆O₈S
Molecular Weight:987.189
Hs Code.:

(2S,3S,4R,5R,6S)-2-(5-Azido-pentyloxymethyl)-6-[2-(1-benzenesulfonyl-1H-indol-3-yl)-ethoxy]-4-benzyloxy-5-(1-trityl-1H-imidazol-4-ylmethoxy)-tetrahydro-pyran-3-ol

Synonyms:(2S,3S,4R,5R,6S)-2-(5-Azido-pentyloxymethyl)-6-[2-(1-benzenesulfonyl-1H-indol-3-yl)-ethoxy]-4-benzyloxy-5-(1-trityl-1H-imidazol-4-ylmethoxy)-tetrahydro-pyran-3-ol

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Chemical Property of (2S,3S,4R,5R,6S)-2-(5-Azido-pentyloxymethyl)-6-[2-(1-benzenesulfonyl-1H-indol-3-yl)-ethoxy]-4-benzyloxy-5-(1-trityl-1H-imidazol-4-ylmethoxy)-tetrahydro-pyran-3-ol

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Technology Process of (2S,3S,4R,5R,6S)-2-(5-Azido-pentyloxymethyl)-6-[2-(1-benzenesulfonyl-1H-indol-3-yl)-ethoxy]-4-benzyloxy-5-(1-trityl-1H-imidazol-4-ylmethoxy)-tetrahydro-pyran-3-ol

There total 11 articles about (2S,3S,4R,5R,6S)-2-(5-Azido-pentyloxymethyl)-6-[2-(1-benzenesulfonyl-1H-indol-3-yl)-ethoxy]-4-benzyloxy-5-(1-trityl-1H-imidazol-4-ylmethoxy)-tetrahydro-pyran-3-ol 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: 94.0%

: 543697-39-8
3-{2-[(2S,3R,4R,5S,6S)-6-(5-Azido-pentyloxymethyl)-4-benzyloxy-5-(4-methoxy-benzyloxy)-3-(1-trityl-1H-imidazol-4-ylmethoxy)-tetrahydro-pyran-2-yloxy]-ethyl}-1-benzenesulfonyl-1H-indole

: 543697-13-8
(2S,3S,4R,5R,6S)-2-(5-Azido-pentyloxymethyl)-6-[2-(1-benzenesulfonyl-1H-indol-3-yl)-ethoxy]-4-benzyloxy-5-(1-trityl-1H-imidazol-4-ylmethoxy)-tetrahydro-pyran-3-ol

Guidance literature:: With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; at 5 ℃; for 8h; pH=6;
DOI:10.1021/jm0205088

Reference yield:

: 170220-11-8
5-azido-1-pentanol

: 543697-13-8
(2S,3S,4R,5R,6S)-2-(5-Azido-pentyloxymethyl)-6-[2-(1-benzenesulfonyl-1H-indol-3-yl)-ethoxy]-4-benzyloxy-5-(1-trityl-1H-imidazol-4-ylmethoxy)-tetrahydro-pyran-3-ol

Guidance literature:: Multi-step reaction with 5 steps

1.1: 2,6-di-t-butyl-4-methyl-pyridine / CH₂Cl₂ / 0.25 h / 0 °C

2.1: 66 percent / CH₂Cl₂ / 12 h

3.1: 88 percent / tetrabutylammonium fluoride / tetrahydrofuran / 25 h / 20 °C

4.1: sodium hydride / tetrahydrofuran; dimethylformamide / 0.17 h

4.2: 66 percent / tetrabutylammonium iodide / tetrahydrofuran; dimethylformamide / 1 h / sonication

5.1: 94 percent / DDQ / CH₂Cl₂ / 8 h / 5 °C / pH 6

With 2,6-di-tert-butyl-4-methylpyridine; tetrabutyl ammonium fluoride; sodium hydride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jm0205088

Reference yield:

: 170220-06-1
5-azidopentyl trifluoromethanesulfonate

: 543697-13-8
(2S,3S,4R,5R,6S)-2-(5-Azido-pentyloxymethyl)-6-[2-(1-benzenesulfonyl-1H-indol-3-yl)-ethoxy]-4-benzyloxy-5-(1-trityl-1H-imidazol-4-ylmethoxy)-tetrahydro-pyran-3-ol

Guidance literature:: Multi-step reaction with 4 steps

1.1: 66 percent / CH₂Cl₂ / 12 h

2.1: 88 percent / tetrabutylammonium fluoride / tetrahydrofuran / 25 h / 20 °C

3.1: sodium hydride / tetrahydrofuran; dimethylformamide / 0.17 h

3.2: 66 percent / tetrabutylammonium iodide / tetrahydrofuran; dimethylformamide / 1 h / sonication

4.1: 94 percent / DDQ / CH₂Cl₂ / 8 h / 5 °C / pH 6

With tetrabutyl ammonium fluoride; sodium hydride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jm0205088