(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

Base Information

Chemical Name:(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
CAS No.:543697-38-7
Molecular Formula:C₄₂H₄₈N₄O₉S
Molecular Weight:784.931
Hs Code.:

Synonyms:(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

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Chemical Property of (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

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Technology Process of (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

There total 10 articles about (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 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: 88.0%

: 543697-12-7
3-{2-[(2S,3R,4R,5S,6S)-6-(5-Azido-pentyloxymethyl)-4-benzyloxy-5-(4-methoxy-benzyloxy)-3-triisopropylsilanyloxy-tetrahydro-pyran-2-yloxy]-ethyl}-1-benzenesulfonyl-1H-indole

: 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

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 25h;
DOI:10.1021/jm0205088

Reference yield:

: 2186-92-7
p-Anisaldehyde dimethyl acetal

: 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

Guidance literature:: Multi-step reaction with 7 steps

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

2: 76 percent / DMSO; acetic anhydride / 72 h / 20 °C

3: 88 percent / L-selectride / tetrahydrofuran / 0.33 h / -78 °C

4: 87 percent / 2,6-lutidine / CH₂Cl₂ / 16 h / 20 °C

5: 92 percent / DIBALH / CH₂Cl₂; toluene / 3 h / -60 - -20 °C

6: 66 percent / CH₂Cl₂ / 12 h

7: 88 percent / tetrabutylammonium fluoride / tetrahydrofuran / 25 h / 20 °C

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

Reference yield:

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

: 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

Guidance literature:: Multi-step reaction with 3 steps

1: 2,6-di-t-butyl-4-methyl-pyridine / CH₂Cl₂ / 0.25 h / 0 °C

2: 66 percent / CH₂Cl₂ / 12 h

3: 88 percent / tetrabutylammonium fluoride / tetrahydrofuran / 25 h / 20 °C

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