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

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Chemical Name: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
CAS No.:543697-39-8
Molecular Formula:C₆₅H₆₆N₆O₉S
Molecular Weight:1107.34
Hs Code.:

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

Synonyms: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

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Chemical Property of 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

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Technology Process of 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

There total 11 articles about 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 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: 66.0%

: 103057-10-9
4-chloromethyl-1-tritylimidazole

: 543697-38-7
(2S,3R,4S,5S,6S)-6-(5-Azido-pentyloxymethyl)-2-[2-(1-benzenesulfonyl-1H-indol-3-yl)-ethoxy]-4-benzyloxy-5-(4-methoxy-benzyloxy)-tetrahydro-pyran-3-ol

: 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

Guidance literature:: 4-chloromethyl-1-tritylimidazole; With sodium hydride; In tetrahydrofuran; N,N-dimethyl-formamide; for 0.166667h;

(2S,3R,4S,5S,6S)-6-(5-Azido-pentyloxymethyl)-2-[2-(1-benzenesulfonyl-1H-indol-3-yl)-ethoxy]-4-benzyloxy-5-(4-methoxy-benzyloxy)-tetrahydro-pyran-3-ol; With tetra-(n-butyl)ammonium iodide; In tetrahydrofuran; N,N-dimethyl-formamide; for 1h; sonication;
DOI:10.1021/jm0205088

Reference yield:

: 2186-92-7
p-Anisaldehyde dimethyl acetal

: 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

Guidance literature:: Multi-step reaction with 8 steps

1.1: 78 percent / camphorosulfonic acid / CHCl₃ / 1 h / Heating

2.1: 76 percent / DMSO; acetic anhydride / 72 h / 20 °C

3.1: 88 percent / L-selectride / tetrahydrofuran / 0.33 h / -78 °C

4.1: 87 percent / 2,6-lutidine / CH₂Cl₂ / 16 h / 20 °C

5.1: 92 percent / DIBALH / CH₂Cl₂; toluene / 3 h / -60 - -20 °C

6.1: 66 percent / CH₂Cl₂ / 12 h

7.1: 88 percent / tetrabutylammonium fluoride / tetrahydrofuran / 25 h / 20 °C

8.1: sodium hydride / tetrahydrofuran; dimethylformamide / 0.17 h

8.2: 66 percent / tetrabutylammonium iodide / tetrahydrofuran; dimethylformamide / 1 h / sonication

With 2,6-dimethylpyridine; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; acetic anhydride; L-Selectride; sodium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; In tetrahydrofuran; dichloromethane; chloroform; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jm0205088

Reference yield:

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

: 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

Guidance literature:: Multi-step reaction with 4 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

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