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

Base Information

• Chemical Name: 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
• CAS No.: 543697-26-3
• Molecular Formula: C₄₈H₅₅N₃O₈S
• Molecular Weight: 834.046

Synonyms: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

Chemical Property of 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

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Technology Process of 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

There total 3 articles about 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 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: 80.0%

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 (543697-52-5) → 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 (543697-26-3)

Guidance literature:

With triphenylphosphine; In tetrahydrofuran; for 2h; Heating;

DOI:10.1021/jm0205088

Reference yield:

3-(chloromethyl)-6-methylpyridine monohydrochloride (106651-81-4) → 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 (543697-26-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium hydride / dimethylformamide / 1 h / 20 °C

1.2: 60 percent / sodium hydride; tetrabutylammonium iodide / tetrahydrofuran; dimethylformamide / 0.5 h

2.1: 80 percent / aq. triphenylphosphine / tetrahydrofuran / 2 h / Heating

With sodium hydride; triphenylphosphine; In tetrahydrofuran; N,N-dimethyl-formamide; 2.1: Staudinger reduction;

DOI:10.1021/jm0205088

Reference yield:

(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 → 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 (543697-26-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium hydride / dimethylformamide / 1 h / 20 °C

1.2: 60 percent / sodium hydride; tetrabutylammonium iodide / tetrahydrofuran; dimethylformamide / 0.5 h

2.1: 80 percent / aq. triphenylphosphine / tetrahydrofuran / 2 h / Heating

With sodium hydride; triphenylphosphine; In tetrahydrofuran; N,N-dimethyl-formamide; 2.1: Staudinger reduction;

DOI:10.1021/jm0205088

upstream raw materials:

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

3-(chloromethyl)-6-methylpyridine monohydrochloride

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