(2R,3R,4S,5R,6S)-2-Azidomethyl-4,5-dimethoxy-3-pent-4-enyloxy-6-phenylsulfanyl-tetrahydro-pyran

Base Information

Chemical Name:(2R,3R,4S,5R,6S)-2-Azidomethyl-4,5-dimethoxy-3-pent-4-enyloxy-6-phenylsulfanyl-tetrahydro-pyran
CAS No.:511274-68-3
Molecular Formula:C₁₉H₂₇N₃O₄S
Molecular Weight:393.507
Hs Code.:

Synonyms:(2R,3R,4S,5R,6S)-2-Azidomethyl-4,5-dimethoxy-3-pent-4-enyloxy-6-phenylsulfanyl-tetrahydro-pyran

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Chemical Property of (2R,3R,4S,5R,6S)-2-Azidomethyl-4,5-dimethoxy-3-pent-4-enyloxy-6-phenylsulfanyl-tetrahydro-pyran

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Technology Process of (2R,3R,4S,5R,6S)-2-Azidomethyl-4,5-dimethoxy-3-pent-4-enyloxy-6-phenylsulfanyl-tetrahydro-pyran

There total 4 articles about (2R,3R,4S,5R,6S)-2-Azidomethyl-4,5-dimethoxy-3-pent-4-enyloxy-6-phenylsulfanyl-tetrahydro-pyran 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: 52.0%

: 511274-64-9
(2R,3R,4S,5R,6S)-2-Azidomethyl-4,5-dimethoxy-6-phenylsulfanyl-tetrahydro-pyran-3-ol

: 1119-51-3
bromopentene

: 511274-68-3
(2R,3R,4S,5R,6S)-2-Azidomethyl-4,5-dimethoxy-3-pent-4-enyloxy-6-phenylsulfanyl-tetrahydro-pyran

Guidance literature:: With tetra-(n-butyl)ammonium iodide; sodium hydride; In tetrahydrofuran; at 20 ℃; for 24h;
DOI:10.1021/jo051021k

Reference yield:

: 511274-40-1
(2R,3R,4S,5R,6S)-2-Hydroxymethyl-4,5-dimethoxy-6-phenylsulfanyl-tetrahydro-pyran-3-ol

: 511274-68-3
(2R,3R,4S,5R,6S)-2-Azidomethyl-4,5-dimethoxy-3-pent-4-enyloxy-6-phenylsulfanyl-tetrahydro-pyran

Guidance literature:: Multi-step reaction with 3 steps

1: 90 percent / triethylamine / CH₂Cl₂ / 24 h / 20 °C

2: 84 percent / NaN₃; 15-crown-5 / dimethylformamide / 48 h / 60 °C

3: 52 percent / tetrabutylammonium iodide; NaH / tetrahydrofuran; various solvent(s) / 24 h / 20 °C

With sodium azide; 15-crown-5; tetra-(n-butyl)ammonium iodide; sodium hydride; triethylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo051021k

Reference yield:

: 870537-88-5
Toluene-4-sulfonic acid (2R,3R,4S,5R,6S)-3-hydroxy-4,5-dimethoxy-6-phenylsulfanyl-tetrahydro-pyran-2-ylmethyl ester

: 511274-68-3
(2R,3R,4S,5R,6S)-2-Azidomethyl-4,5-dimethoxy-3-pent-4-enyloxy-6-phenylsulfanyl-tetrahydro-pyran

Guidance literature:: Multi-step reaction with 2 steps

1: 84 percent / NaN₃; 15-crown-5 / dimethylformamide / 48 h / 60 °C

2: 52 percent / tetrabutylammonium iodide; NaH / tetrahydrofuran; various solvent(s) / 24 h / 20 °C

With sodium azide; 15-crown-5; tetra-(n-butyl)ammonium iodide; sodium hydride; In tetrahydrofuran; N,N-dimethyl-formamide;
DOI:10.1021/jo051021k