(3aS,4S,6aR)-4-((E)-4-Benzyloxy-but-1-enyl)-2,2-dimethyl-5-(2-nitro-benzenesulfonyl)-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole

Base Information

Chemical Name:(3aS,4S,6aR)-4-((E)-4-Benzyloxy-but-1-enyl)-2,2-dimethyl-5-(2-nitro-benzenesulfonyl)-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole
CAS No.:570385-49-8
Molecular Formula:C₂₄H₂₈N₂O₇S
Molecular Weight:488.562
Hs Code.:

Synonyms:(3aS,4S,6aR)-4-((E)-4-Benzyloxy-but-1-enyl)-2,2-dimethyl-5-(2-nitro-benzenesulfonyl)-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole

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Chemical Property of (3aS,4S,6aR)-4-((E)-4-Benzyloxy-but-1-enyl)-2,2-dimethyl-5-(2-nitro-benzenesulfonyl)-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole

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Technology Process of (3aS,4S,6aR)-4-((E)-4-Benzyloxy-but-1-enyl)-2,2-dimethyl-5-(2-nitro-benzenesulfonyl)-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole

There total 8 articles about (3aS,4S,6aR)-4-((E)-4-Benzyloxy-but-1-enyl)-2,2-dimethyl-5-(2-nitro-benzenesulfonyl)-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole 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: 69.0%

: 54314-85-1
(3-benzyloxypropyl)triphenylphosphonium bromide

: 570385-42-1
(3aS,4R,6aR)-2,2-Dimethyl-5-(2-nitro-benzenesulfonyl)-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-4-carbaldehyde

: 570385-49-8
(3aS,4S,6aR)-4-((E)-4-Benzyloxy-but-1-enyl)-2,2-dimethyl-5-(2-nitro-benzenesulfonyl)-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole

Guidance literature:: With sodium hexamethyldisilazane; In tetrahydrofuran; at -78 - 0 ℃;
DOI:10.1016/S0040-4039(03)00512-4

Reference yield:

: 1694-92-4
2-Nitrobenzenesulfonyl chloride

: 570385-49-8
(3aS,4S,6aR)-4-((E)-4-Benzyloxy-but-1-enyl)-2,2-dimethyl-5-(2-nitro-benzenesulfonyl)-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole

Guidance literature:: Multi-step reaction with 5 steps

1: 93 percent / Et₃N / CH₂Cl₂

2: 100 percent / PPh₃; diethyl azodicarboxylate / tetrahydrofuran

3: 70 percent / TFA / tetrahydrofuran; H₂O

4: 96 percent / NaIO₄; silica gel / CH₂Cl₂; H₂O

5: 69 percent / NaHMDS / tetrahydrofuran / -78 - 0 °C

With sodium periodate; sodium hexamethyldisilazane; silica gel; triethylamine; triphenylphosphine; trifluoroacetic acid; diethylazodicarboxylate; In tetrahydrofuran; dichloromethane; water; 2: Mitsunobu reaction / 5: Wittig reaction;
DOI:10.1016/S0040-4039(03)00512-4

Reference yield:

: 7306-64-1,14440-56-3,23262-80-8,27108-15-2,49561-21-9,67642-42-6
2,3,5,6-di-O-isopropylidene-D-mannono-1,4-lactone

: 570385-49-8
(3aS,4S,6aR)-4-((E)-4-Benzyloxy-but-1-enyl)-2,2-dimethyl-5-(2-nitro-benzenesulfonyl)-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole

Guidance literature:: Multi-step reaction with 7 steps

1: 80 percent / NH₃ / methanol

2: 76 percent / LiAlH₄ / tetrahydrofuran / Heating

3: 93 percent / Et₃N / CH₂Cl₂

4: 100 percent / PPh₃; diethyl azodicarboxylate / tetrahydrofuran

5: 70 percent / TFA / tetrahydrofuran; H₂O

6: 96 percent / NaIO₄; silica gel / CH₂Cl₂; H₂O

7: 69 percent / NaHMDS / tetrahydrofuran / -78 - 0 °C

With sodium periodate; lithium aluminium tetrahydride; ammonia; sodium hexamethyldisilazane; silica gel; triethylamine; triphenylphosphine; trifluoroacetic acid; diethylazodicarboxylate; In tetrahydrofuran; methanol; dichloromethane; water; 4: Mitsunobu reaction / 7: Wittig reaction;
DOI:10.1016/S0040-4039(03)00512-4