(2S,3S,4S,5S)-3,4-dibenzyloxy-2,4-dimethyl-5-ethyl-2-iodomethyltetrahydrofuran

Base Information

Chemical Name:(2S,3S,4S,5S)-3,4-dibenzyloxy-2,4-dimethyl-5-ethyl-2-iodomethyltetrahydrofuran
CAS No.:548487-96-3
Molecular Formula:C₂₃H₂₉IO₃
Molecular Weight:480.386
Hs Code.:

Synonyms:(2S,3S,4S,5S)-3,4-dibenzyloxy-2,4-dimethyl-5-ethyl-2-iodomethyltetrahydrofuran

Suppliers and Price of (2S,3S,4S,5S)-3,4-dibenzyloxy-2,4-dimethyl-5-ethyl-2-iodomethyltetrahydrofuran

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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 (2S,3S,4S,5S)-3,4-dibenzyloxy-2,4-dimethyl-5-ethyl-2-iodomethyltetrahydrofuran

Chemical Property:

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Technology Process of (2S,3S,4S,5S)-3,4-dibenzyloxy-2,4-dimethyl-5-ethyl-2-iodomethyltetrahydrofuran

There total 8 articles about (2S,3S,4S,5S)-3,4-dibenzyloxy-2,4-dimethyl-5-ethyl-2-iodomethyltetrahydrofuran 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: 65.0%

: 548487-95-2
(2S,3S,4S,5S)-3,4-dibenzyloxy-2,4-dimethyl-5-ethyl-2-hydroxymethyltetrahydrofuran

: 548487-96-3
(2S,3S,4S,5S)-3,4-dibenzyloxy-2,4-dimethyl-5-ethyl-2-iodomethyltetrahydrofuran

Guidance literature:: With 1H-imidazole; iodine; triphenylphosphine; In benzene; for 0.5h; Heating;
DOI:10.1021/ja034865z

Reference yield:

: 548488-20-6
(2S,3S,4S,5S)-4-dimethylphenylsilyl-3-hydroxy-2-hydroxymethyl-2,4-dimethyl-5-ethyltetrahydrofuran

: 548487-96-3
(2S,3S,4S,5S)-3,4-dibenzyloxy-2,4-dimethyl-5-ethyl-2-iodomethyltetrahydrofuran

Guidance literature:: Multi-step reaction with 7 steps

1.1: NaH / dimethylformamide / 0.5 h / 0 °C

1.2: 96 percent / n-Bu₄NI / hexane; dimethylformamide / 12 h / 0 - 23 °C

2.1: 85 percent / cumene hydroperoxide; KH; NMP / n-Bu₄NF / tetrahydrofuran / 40 h / 23 °C

3.1: 98 percent / H₂ / Pd/C / ethanol / 24 h / 760 Torr

4.1: 96 percent / imidazole / dimethylformamide / 12 h / 23 °C

5.1: NaH / dimethylformamide / 0.5 h / 0 °C

5.2: 96 percent / n-Bu₄NI / dimethylformamide / 12 h / 0 - 23 °C

6.1: 97 percent / n-Bu₄NF / tetrahydrofuran / 12 h / 23 °C

7.1: 65 percent / Ph₃P; imidazole; I₂ / benzene / 0.5 h / Heating

With 1H-imidazole; 1-methyl-pyrrolidin-2-one; Cumene hydroperoxide; tetrabutyl ammonium fluoride; hydrogen; iodine; potassium hydride; sodium hydride; triphenylphosphine; palladium on activated charcoal; tetrabutyl ammonium fluoride; In tetrahydrofuran; ethanol; N,N-dimethyl-formamide; benzene;
DOI:10.1021/ja034865z

Reference yield:

: 548487-91-8
(2S,3S,4S,5S)-3-benzyloxy-2-benzyloxymethyl-2,4-dimethyl-5-ethyl-4-hydroxytetrahydrofuran

: 548487-96-3
(2S,3S,4S,5S)-3,4-dibenzyloxy-2,4-dimethyl-5-ethyl-2-iodomethyltetrahydrofuran

Guidance literature:: Multi-step reaction with 5 steps

1.1: 98 percent / H₂ / Pd/C / ethanol / 24 h / 760 Torr

2.1: 96 percent / imidazole / dimethylformamide / 12 h / 23 °C

3.1: NaH / dimethylformamide / 0.5 h / 0 °C

3.2: 96 percent / n-Bu₄NI / dimethylformamide / 12 h / 0 - 23 °C

4.1: 97 percent / n-Bu₄NF / tetrahydrofuran / 12 h / 23 °C

5.1: 65 percent / Ph₃P; imidazole; I₂ / benzene / 0.5 h / Heating

With 1H-imidazole; tetrabutyl ammonium fluoride; hydrogen; iodine; sodium hydride; triphenylphosphine; palladium on activated charcoal; In tetrahydrofuran; ethanol; N,N-dimethyl-formamide; benzene;
DOI:10.1021/ja034865z