(3aR,4S,5R,6aR)-4-(benzyloxy)-5-(iodomethyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole

Base Information

Chemical Name:(3aR,4S,5R,6aR)-4-(benzyloxy)-5-(iodomethyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole
CAS No.:29580-99-2
Molecular Formula:C₁₅H₁₉IO₄
Molecular Weight:390.218
Hs Code.:

Synonyms:(3aR,4S,5R,6aR)-4-(benzyloxy)-5-(iodomethyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (3aR,4S,5R,6aR)-4-(benzyloxy)-5-(iodomethyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole

Chemical Property:

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Technology Process of (3aR,4S,5R,6aR)-4-(benzyloxy)-5-(iodomethyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole

There total 7 articles about (3aR,4S,5R,6aR)-4-(benzyloxy)-5-(iodomethyl)-2,2-dimethyltetrahydrofuro[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: 90.0%

: 34370-91-7,59358-33-7,68354-70-1,70798-12-8,19139-80-1
3-O-benzyl-1,2-O-isopropylidene-α-D-xylofuranose

: 29580-99-2
(3aR,4S,5R,6aR)-4-(benzyloxy)-5-(iodomethyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole

Guidance literature:: With 1H-imidazole; iodine; triphenylphosphine; In toluene; for 0.333333h; Ambient temperature;
DOI:10.1021/jo00006a047

Reference yield:

: 100-39-0
benzyl bromide

: 29580-99-2
(3aR,4S,5R,6aR)-4-(benzyloxy)-5-(iodomethyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole

Guidance literature:: Multi-step reaction with 3 steps

1: 87 percent / sodium hydride; n-tetrabutylammonium iodide / tetrahydrofuran / 12 h / 20 °C

2: 79 percent / HOAc / H₂O / 144 h / 50 °C

3: 88 percent / iodine; imidazole; triphenylphosphine / toluene / 70 °C

With 1H-imidazole; iodine; tetra-(n-butyl)ammonium iodide; sodium hydride; acetic acid; triphenylphosphine; In tetrahydrofuran; water; toluene;
DOI:10.1016/j.carres.2007.07.010

Reference yield:

: 20590-53-8
1,2-O-isopropylidene-5-O-trityl-α-D-xylofuranose

: 29580-99-2
(3aR,4S,5R,6aR)-4-(benzyloxy)-5-(iodomethyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole

Guidance literature:: Multi-step reaction with 3 steps

1: 87 percent / sodium hydride; n-tetrabutylammonium iodide / tetrahydrofuran / 12 h / 20 °C

2: 79 percent / HOAc / H₂O / 144 h / 50 °C

3: 88 percent / iodine; imidazole; triphenylphosphine / toluene / 70 °C

With 1H-imidazole; iodine; tetra-(n-butyl)ammonium iodide; sodium hydride; acetic acid; triphenylphosphine; In tetrahydrofuran; water; toluene;
DOI:10.1016/j.carres.2007.07.010