(3aS,4S,5S,6R,6aS)-4-Azido-6-benzyloxy-5-fluoro-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxole

Base Information

Chemical Name:(3aS,4S,5S,6R,6aS)-4-Azido-6-benzyloxy-5-fluoro-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxole
CAS No.:869711-19-3
Molecular Formula:C₁₅H₁₈FN₃O₃
Molecular Weight:307.325
Hs Code.:

Synonyms:(3aS,4S,5S,6R,6aS)-4-Azido-6-benzyloxy-5-fluoro-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxole

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Chemical Property of (3aS,4S,5S,6R,6aS)-4-Azido-6-benzyloxy-5-fluoro-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxole

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Technology Process of (3aS,4S,5S,6R,6aS)-4-Azido-6-benzyloxy-5-fluoro-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxole

There total 7 articles about (3aS,4S,5S,6R,6aS)-4-Azido-6-benzyloxy-5-fluoro-2,2-dimethyl-tetrahydro-cyclopenta[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: 77.0%

: 869711-14-8
(3aS,4R,5R,6S,6aS)-4-Azido-6-benzyloxy-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-5-ol

: 869711-19-3
(3aS,4S,5S,6R,6aS)-4-Azido-6-benzyloxy-5-fluoro-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxole

Guidance literature:: (3aS,4R,5R,6S,6aS)-4-Azido-6-benzyloxy-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-5-ol; With trifluoromethylsulfonic anhydride; In pyridine; dichloromethane;

With tris(dimethylamino)sulfonium trimethylsilyldifluoride; In tetrahydrofuran;
DOI:10.1016/j.tetlet.2005.08.163

Reference yield:

: (1S,2S,5S)-5-Benzyloxy-cyclopent-3-ene-1,2-diol

: 869711-19-3
(3aS,4S,5S,6R,6aS)-4-Azido-6-benzyloxy-5-fluoro-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxole

Guidance literature:: Multi-step reaction with 4 steps

1.1: mCPBA / CH₂Cl₂

2.1: NaN₃ / dimethylformamide; H₂O

3.1: pTSA / acetone

4.1: Tf₂O / pyridine; CH₂Cl₂

4.2: 77 percent / TASF / tetrahydrofuran

With sodium azide; trifluoromethylsulfonic anhydride; toluene-4-sulfonic acid; 3-chloro-benzenecarboperoxoic acid; In pyridine; dichloromethane; water; N,N-dimethyl-formamide; acetone;
DOI:10.1016/j.tetlet.2005.08.163

Reference yield:

: (2R,3S,4R)-4-Benzyloxy-6-oxa-bicyclo[3.1.0]hexane-2,3-diol

: 869711-19-3
(3aS,4S,5S,6R,6aS)-4-Azido-6-benzyloxy-5-fluoro-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxole

Guidance literature:: Multi-step reaction with 3 steps

1.1: NaN₃ / dimethylformamide; H₂O

2.1: pTSA / acetone

3.1: Tf₂O / pyridine; CH₂Cl₂

3.2: 77 percent / TASF / tetrahydrofuran

With sodium azide; trifluoromethylsulfonic anhydride; toluene-4-sulfonic acid; In pyridine; dichloromethane; water; N,N-dimethyl-formamide; acetone;
DOI:10.1016/j.tetlet.2005.08.163