2-[(2R,3R,4S,5R,6R)-2-(5-Azido-pentyloxymethyl)-4,5-bis-benzyloxy-6-methoxy-tetrahydro-pyran-3-yloxymethyl]-pyrazine

Base Information

Chemical Name:2-[(2R,3R,4S,5R,6R)-2-(5-Azido-pentyloxymethyl)-4,5-bis-benzyloxy-6-methoxy-tetrahydro-pyran-3-yloxymethyl]-pyrazine
CAS No.:543697-46-7
Molecular Formula:C₃₁H₃₉N₅O₆
Molecular Weight:577.681
Hs Code.:

Synonyms:2-[(2R,3R,4S,5R,6R)-2-(5-Azido-pentyloxymethyl)-4,5-bis-benzyloxy-6-methoxy-tetrahydro-pyran-3-yloxymethyl]-pyrazine

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of 2-[(2R,3R,4S,5R,6R)-2-(5-Azido-pentyloxymethyl)-4,5-bis-benzyloxy-6-methoxy-tetrahydro-pyran-3-yloxymethyl]-pyrazine

Chemical Property:

Purity/Quality:: 98% ^*data from raw suppliers

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Technology Process of 2-[(2R,3R,4S,5R,6R)-2-(5-Azido-pentyloxymethyl)-4,5-bis-benzyloxy-6-methoxy-tetrahydro-pyran-3-yloxymethyl]-pyrazine

There total 4 articles about 2-[(2R,3R,4S,5R,6R)-2-(5-Azido-pentyloxymethyl)-4,5-bis-benzyloxy-6-methoxy-tetrahydro-pyran-3-yloxymethyl]-pyrazine 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: 72.0%

: 39204-47-2
2-(chloromethyl)pyrazine

: 543697-42-3
(2R,3R,4S,5R,6R)-2-(5-Azido-pentyloxymethyl)-4,5-bis-benzyloxy-6-methoxy-tetrahydro-pyran-3-ol

: 543697-46-7
2-[(2R,3R,4S,5R,6R)-2-(5-Azido-pentyloxymethyl)-4,5-bis-benzyloxy-6-methoxy-tetrahydro-pyran-3-yloxymethyl]-pyrazine

Guidance literature:: (2R,3R,4S,5R,6R)-2-(5-Azido-pentyloxymethyl)-4,5-bis-benzyloxy-6-methoxy-tetrahydro-pyran-3-ol; With sodium hydride; In N,N-dimethyl-formamide; at 0 ℃;

2-(chloromethyl)pyrazine; With tetra-(n-butyl)ammonium iodide; In N,N-dimethyl-formamide; at 0 ℃;
DOI:10.1021/jm0205088

Reference yield:

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

: 543697-46-7
2-[(2R,3R,4S,5R,6R)-2-(5-Azido-pentyloxymethyl)-4,5-bis-benzyloxy-6-methoxy-tetrahydro-pyran-3-yloxymethyl]-pyrazine

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: NaH / 0.25 h / 0 °C

2.2: 88 percent / tetrahydrofuran / 1.5 h / 0 °C

3.1: 80 percent / aq. 2,3-dicyano-5,6-dichloro-1,4-quinone / CH₂Cl₂ / 1.25 h / 0 - 20 °C

4.1: NaH / dimethylformamide / 0 °C

4.2: 72 percent / tetrabutylammonium iodide / dimethylformamide / 0 °C

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

Reference yield:

: 170220-06-1
5-azidopentyl trifluoromethanesulfonate

: 543697-46-7
2-[(2R,3R,4S,5R,6R)-2-(5-Azido-pentyloxymethyl)-4,5-bis-benzyloxy-6-methoxy-tetrahydro-pyran-3-yloxymethyl]-pyrazine

Guidance literature:: Multi-step reaction with 3 steps

1.1: NaH / 0.25 h / 0 °C

1.2: 88 percent / tetrahydrofuran / 1.5 h / 0 °C

2.1: 80 percent / aq. 2,3-dicyano-5,6-dichloro-1,4-quinone / CH₂Cl₂ / 1.25 h / 0 - 20 °C

3.1: NaH / dimethylformamide / 0 °C

3.2: 72 percent / tetrabutylammonium iodide / dimethylformamide / 0 °C

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