(2S,3R,4S,5S)-3-acetoxy-2-acetoxymethyl-4-benzylamino-5-methoxy-5-(2-methoxyethyl)tetrahydrofuran

Base Information

Chemical Name:(2S,3R,4S,5S)-3-acetoxy-2-acetoxymethyl-4-benzylamino-5-methoxy-5-(2-methoxyethyl)tetrahydrofuran
CAS No.:1392007-68-9
Molecular Formula:C₂₀H₂₉NO₇
Molecular Weight:395.453
Hs Code.:

Synonyms:(2S,3R,4S,5S)-3-acetoxy-2-acetoxymethyl-4-benzylamino-5-methoxy-5-(2-methoxyethyl)tetrahydrofuran

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Chemical Property of (2S,3R,4S,5S)-3-acetoxy-2-acetoxymethyl-4-benzylamino-5-methoxy-5-(2-methoxyethyl)tetrahydrofuran

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Technology Process of (2S,3R,4S,5S)-3-acetoxy-2-acetoxymethyl-4-benzylamino-5-methoxy-5-(2-methoxyethyl)tetrahydrofuran

There total 4 articles about (2S,3R,4S,5S)-3-acetoxy-2-acetoxymethyl-4-benzylamino-5-methoxy-5-(2-methoxyethyl)tetrahydrofuran 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: 83.0%

: 1392007-67-8
(2S,3R,4S,5S)-4-benzylamino-2-hydroxymethyl-5-methoxy-5-(2-methoxyethyl)-tetrahydrofuran-3-ol

: 108-24-7
acetic anhydride

: 1392007-68-9
(2S,3R,4S,5S)-3-acetoxy-2-acetoxymethyl-4-benzylamino-5-methoxy-5-(2-methoxyethyl)tetrahydrofuran

Guidance literature:: With dmap; triethylamine; In dichloromethane; at 20 ℃; Inert atmosphere;
DOI:10.1002/ejoc.201200158

Reference yield:

: 1392007-21-4
(3S,4'R,5'S)-2-benzyl-3-(5'-hydroxymethyl-2',2'-dimethyl-1',3'-dioxolan-4'-yl)-4-methoxy-3,6-dihydro-2H-[1,2]oxazine

: 1392007-68-9
(2S,3R,4S,5S)-3-acetoxy-2-acetoxymethyl-4-benzylamino-5-methoxy-5-(2-methoxyethyl)tetrahydrofuran

Guidance literature:: Multi-step reaction with 3 steps

1: samarium diiodide / tetrahydrofuran / 4 h / 20 °C / Inert atmosphere

2: hydrogenchloride / 120 h / 20 °C / Inert atmosphere

3: dmap; triethylamine / dichloromethane / 20 °C / Inert atmosphere

With hydrogenchloride; dmap; samarium diiodide; triethylamine; In tetrahydrofuran; dichloromethane;
DOI:10.1002/ejoc.201200158

Reference yield:

: (2S,3S,4S)-N-benzyl-N-hydroxy-3,4-isopropylidenedioxytetrahydrofuran-2-amine

: 1392007-68-9
(2S,3R,4S,5S)-3-acetoxy-2-acetoxymethyl-4-benzylamino-5-methoxy-5-(2-methoxyethyl)tetrahydrofuran

Guidance literature:: Multi-step reaction with 4 steps

1.1: n-butyllithium / tetrahydrofuran; hexane / 0.08 h / -40 °C / Inert atmosphere

1.2: 8 h / -40 °C / Inert atmosphere

2.1: samarium diiodide / tetrahydrofuran / 4 h / 20 °C / Inert atmosphere

3.1: hydrogenchloride / 120 h / 20 °C / Inert atmosphere

4.1: dmap; triethylamine / dichloromethane / 20 °C / Inert atmosphere

With hydrogenchloride; dmap; n-butyllithium; samarium diiodide; triethylamine; In tetrahydrofuran; hexane; dichloromethane;
DOI:10.1002/ejoc.201200158