(3aR,5R,6R,6aR)-5-((S)-1-Azido-ethyl)-6-(4-methoxy-benzyloxy)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole

Base Information

Chemical Name:(3aR,5R,6R,6aR)-5-((S)-1-Azido-ethyl)-6-(4-methoxy-benzyloxy)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole
CAS No.:199458-27-0
Molecular Formula:C₁₇H₂₃N₃O₅
Molecular Weight:349.387
Hs Code.:

Synonyms:(3aR,5R,6R,6aR)-5-((S)-1-Azido-ethyl)-6-(4-methoxy-benzyloxy)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole

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Chemical Property of (3aR,5R,6R,6aR)-5-((S)-1-Azido-ethyl)-6-(4-methoxy-benzyloxy)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole

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Technology Process of (3aR,5R,6R,6aR)-5-((S)-1-Azido-ethyl)-6-(4-methoxy-benzyloxy)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole

There total 7 articles about (3aR,5R,6R,6aR)-5-((S)-1-Azido-ethyl)-6-(4-methoxy-benzyloxy)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole 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: 88.0%

: 199458-26-9
Toluene-4-sulfonic acid (R)-1-[(3aR,5S,6R,6aR)-6-(4-methoxy-benzyloxy)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl]-ethyl ester

: 199458-27-0
(3aR,5R,6R,6aR)-5-((S)-1-Azido-ethyl)-6-(4-methoxy-benzyloxy)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole

Guidance literature:: With sodium azide; In N,N-dimethyl-formamide; at 80 ℃; for 1.5h;
DOI:10.1055/s-1997-1003

Reference yield:

: 14686-89-6
(1,2:5,6)-di-O-isopropylidene-D-gulose

: 199458-27-0
(3aR,5R,6R,6aR)-5-((S)-1-Azido-ethyl)-6-(4-methoxy-benzyloxy)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole

Guidance literature:: Multi-step reaction with 6 steps

1: 95 percent / NaH, nBu₄NI / tetrahydrofuran / 12 h / Ambient temperature

2: 89 percent / 90percent AcOH / H₂O / 2.5 h / 40 °C

3: 82 percent / Et₃N, pyridine, DMAP / CH₂Cl₂ / 2.5 h / 0 - 25 °C

4: 80 percent / NaI, nBu₃SnH, AIBN / 1,2-dimethoxy-ethane / 1.5 h / 80 °C

5: 80 percent / Et₃N, DMAP / pyridine / 3.5 h / 70 °C

6: 88 percent / NaN₃ / dimethylformamide / 1.5 h / 80 °C

With pyridine; dmap; sodium azide; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; tetra-(n-butyl)ammonium iodide; sodium hydride; acetic acid; triethylamine; sodium iodide; In tetrahydrofuran; pyridine; 1,2-dimethoxyethane; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1055/s-1997-1003

Reference yield:

: 69940-04-1,142226-16-2,109536-51-8
(R)-1-[(3aR,5R,6R,6aR)-6-(4-methoxybenzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl]ethane-1,2-diol

: 199458-27-0
(3aR,5R,6R,6aR)-5-((S)-1-Azido-ethyl)-6-(4-methoxy-benzyloxy)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole

Guidance literature:: Multi-step reaction with 4 steps

1: 82 percent / Et₃N, pyridine, DMAP / CH₂Cl₂ / 2.5 h / 0 - 25 °C

2: 80 percent / NaI, nBu₃SnH, AIBN / 1,2-dimethoxy-ethane / 1.5 h / 80 °C

3: 80 percent / Et₃N, DMAP / pyridine / 3.5 h / 70 °C

4: 88 percent / NaN₃ / dimethylformamide / 1.5 h / 80 °C

With pyridine; dmap; sodium azide; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; triethylamine; sodium iodide; In pyridine; 1,2-dimethoxyethane; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1055/s-1997-1003