3-{2-[(2R,3R,4S,5R,6R)-6-(5-Azido-pentyloxymethyl)-3,4-bis-benzyloxy-5-(6-methyl-pyridin-3-ylmethoxy)-tetrahydro-pyran-2-yloxy]-ethyl}-1-benzenesulfonyl-1H-indole

Base Information

Chemical Name:3-{2-[(2R,3R,4S,5R,6R)-6-(5-Azido-pentyloxymethyl)-3,4-bis-benzyloxy-5-(6-methyl-pyridin-3-ylmethoxy)-tetrahydro-pyran-2-yloxy]-ethyl}-1-benzenesulfonyl-1H-indole
CAS No.:543697-52-5
Molecular Formula:C₄₈H₅₃N₅O₈S
Molecular Weight:860.044
Hs Code.:

3-{2-[(2R,3R,4S,5R,6R)-6-(5-Azido-pentyloxymethyl)-3,4-bis-benzyloxy-5-(6-methyl-pyridin-3-ylmethoxy)-tetrahydro-pyran-2-yloxy]-ethyl}-1-benzenesulfonyl-1H-indole

Synonyms:3-{2-[(2R,3R,4S,5R,6R)-6-(5-Azido-pentyloxymethyl)-3,4-bis-benzyloxy-5-(6-methyl-pyridin-3-ylmethoxy)-tetrahydro-pyran-2-yloxy]-ethyl}-1-benzenesulfonyl-1H-indole

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Chemical Property of 3-{2-[(2R,3R,4S,5R,6R)-6-(5-Azido-pentyloxymethyl)-3,4-bis-benzyloxy-5-(6-methyl-pyridin-3-ylmethoxy)-tetrahydro-pyran-2-yloxy]-ethyl}-1-benzenesulfonyl-1H-indole

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Technology Process of 3-{2-[(2R,3R,4S,5R,6R)-6-(5-Azido-pentyloxymethyl)-3,4-bis-benzyloxy-5-(6-methyl-pyridin-3-ylmethoxy)-tetrahydro-pyran-2-yloxy]-ethyl}-1-benzenesulfonyl-1H-indole

There total 1 articles about 3-{2-[(2R,3R,4S,5R,6R)-6-(5-Azido-pentyloxymethyl)-3,4-bis-benzyloxy-5-(6-methyl-pyridin-3-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: 60.0%

: 106651-81-4
3-(chloromethyl)-6-methylpyridine monohydrochloride

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

: 543697-52-5
3-{2-[(2R,3R,4S,5R,6R)-6-(5-Azido-pentyloxymethyl)-3,4-bis-benzyloxy-5-(6-methyl-pyridin-3-ylmethoxy)-tetrahydro-pyran-2-yloxy]-ethyl}-1-benzenesulfonyl-1H-indole

Guidance literature:: 3-(chloromethyl)-6-methylpyridine monohydrochloride; With sodium hydride; In N,N-dimethyl-formamide; at 20 ℃; for 1h;

(2R,3R,4S,5R,6R)-2-(5-Azido-pentyloxymethyl)-6-[2-(1-benzenesulfonyl-1H-indol-3-yl)-ethoxy]-4,5-bis-benzyloxy-tetrahydro-pyran-3-ol; With tetra-(n-butyl)ammonium iodide; sodium hydride; In tetrahydrofuran; N,N-dimethyl-formamide; for 0.5h;
DOI:10.1021/jm0205088

Reference yield: 80.0%

: 543697-52-5
3-{2-[(2R,3R,4S,5R,6R)-6-(5-Azido-pentyloxymethyl)-3,4-bis-benzyloxy-5-(6-methyl-pyridin-3-ylmethoxy)-tetrahydro-pyran-2-yloxy]-ethyl}-1-benzenesulfonyl-1H-indole

: 543697-26-3
5-[(2R,3R,4S,5R,6R)-6-[2-(1-Benzenesulfonyl-1H-indol-3-yl)-ethoxy]-4,5-bis-benzyloxy-3-(6-methyl-pyridin-3-ylmethoxy)-tetrahydro-pyran-2-ylmethoxy]-pentylamine

Guidance literature:: With triphenylphosphine; In tetrahydrofuran; for 2h; Heating;
DOI:10.1021/jm0205088

Reference yield:

: 543697-52-5
3-{2-[(2R,3R,4S,5R,6R)-6-(5-Azido-pentyloxymethyl)-3,4-bis-benzyloxy-5-(6-methyl-pyridin-3-ylmethoxy)-tetrahydro-pyran-2-yloxy]-ethyl}-1-benzenesulfonyl-1H-indole

: 5-[(2R,3R,4S,5R,6R)-4,5-Bis-benzyloxy-6-[2-(1H-indol-3-yl)-ethoxy]-3-(6-methyl-pyridin-3-ylmethoxy)-tetrahydro-pyran-2-ylmethoxy]-pentylamine

Guidance literature:: Multi-step reaction with 2 steps

1: 80 percent / aq. triphenylphosphine / tetrahydrofuran / 2 h / Heating

2: 33 percent / aq. NaOH / ethanol / 5 h / Heating

With sodium hydroxide; triphenylphosphine; In tetrahydrofuran; ethanol; 1: Staudinger reduction;
DOI:10.1021/jm0205088