(2S,4aR,6R,7R,8R,8aR)-7-Azido-8-benzyloxy-6-fluoro-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine

Base Information

Chemical Name:(2S,4aR,6R,7R,8R,8aR)-7-Azido-8-benzyloxy-6-fluoro-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine
CAS No.:132183-19-8
Molecular Formula:C₂₀H₂₀FN₃O₄
Molecular Weight:385.395
Hs Code.:

Synonyms:(2S,4aR,6R,7R,8R,8aR)-7-Azido-8-benzyloxy-6-fluoro-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine

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Chemical Property of (2S,4aR,6R,7R,8R,8aR)-7-Azido-8-benzyloxy-6-fluoro-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine

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Technology Process of (2S,4aR,6R,7R,8R,8aR)-7-Azido-8-benzyloxy-6-fluoro-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine

There total 7 articles about (2S,4aR,6R,7R,8R,8aR)-7-Azido-8-benzyloxy-6-fluoro-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine 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: 78.0%

: 2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-β-D-galactopyranose

: 132183-20-1
(2S,4aR,6S,7R,8R,8aR)-7-Azido-8-benzyloxy-6-fluoro-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine

: 132183-19-8
(2S,4aR,6R,7R,8R,8aR)-7-Azido-8-benzyloxy-6-fluoro-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine

Guidance literature:: With 4,4'-diaminostilbene-2,2'-disulfonic acid; In tetrahydrofuran;
DOI:10.1016/S0040-4039(00)97201-0

Reference yield:

: 1125-88-8
benzaldehyde dimethyl acetal

: 132183-19-8
(2S,4aR,6R,7R,8R,8aR)-7-Azido-8-benzyloxy-6-fluoro-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine

Guidance literature:: Multi-step reaction with 4 steps

1: p-TsOH / acetonitrile

2: 85 percent / NaH / tetrahydrofuran / Heating

3: 97 percent / n-Bu₄NF, AcOH / tetrahydrofuran

4: 78 percent / DAST / tetrahydrofuran

With tetrabutyl ammonium fluoride; sodium hydride; toluene-4-sulfonic acid; acetic acid; 4,4'-diaminostilbene-2,2'-disulfonic acid; In tetrahydrofuran; acetonitrile;
DOI:10.1016/S0040-4039(00)97201-0

Reference yield:

: 132183-13-2
(2R,3R,4R,5R)-2-(acetoxymethyl)-5-azido-6-hydroxytetrahydro-2H-pyran-3,4-diyl diacetate

: 132183-19-8
(2S,4aR,6R,7R,8R,8aR)-7-Azido-8-benzyloxy-6-fluoro-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine

Guidance literature:: Multi-step reaction with 6 steps

1: 83 percent / imidazole / dimethylformamide / 2.5 h / 60 °C

2: NaOMe / methanol

3: p-TsOH / acetonitrile

4: 85 percent / NaH / tetrahydrofuran / Heating

5: 97 percent / n-Bu₄NF, AcOH / tetrahydrofuran

6: 78 percent / DAST / tetrahydrofuran

With 1H-imidazole; tetrabutyl ammonium fluoride; sodium methylate; sodium hydride; toluene-4-sulfonic acid; acetic acid; 4,4'-diaminostilbene-2,2'-disulfonic acid; In tetrahydrofuran; methanol; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1016/S0040-4039(00)97201-0