(2S,5S)-2-(2’-benzyloxy-(1’S)-hydroxyethyl)-5-(iodomethyl)tetrahydrofuran

Base Information

Chemical Name:(2S,5S)-2-(2’-benzyloxy-(1’S)-hydroxyethyl)-5-(iodomethyl)tetrahydrofuran
CAS No.:1428859-81-7
Molecular Formula:C₁₄H₁₉IO₃
Molecular Weight:362.208
Hs Code.:

Synonyms:(2S,5S)-2-(2’-benzyloxy-(1’S)-hydroxyethyl)-5-(iodomethyl)tetrahydrofuran

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Chemical Property of (2S,5S)-2-(2’-benzyloxy-(1’S)-hydroxyethyl)-5-(iodomethyl)tetrahydrofuran

Chemical Property:

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Technology Process of (2S,5S)-2-(2’-benzyloxy-(1’S)-hydroxyethyl)-5-(iodomethyl)tetrahydrofuran

There total 7 articles about (2S,5S)-2-(2’-benzyloxy-(1’S)-hydroxyethyl)-5-(iodomethyl)tetrahydrofuran 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: 80.0%

: 1428859-77-1
(2R,3S)-1-benzyl-2,3-O-isopropyliden-6-hepten-1,2,3-triol

: 1428859-81-7
(2S,5S)-2-(2’-benzyloxy-(1’S)-hydroxyethyl)-5-(iodomethyl)tetrahydrofuran

Guidance literature:: With iodonium dicollidine perchlorate; In water; acetonitrile; at -10 - 20 ℃; stereoselective reaction; Inert atmosphere;
DOI:10.1021/ol400650v

Reference yield:

: 174953-42-5
(3aS,7aS)-7-bromo-2,2-dimethyl-3a,4,5,7a-tetrahydro-benzo[1,3]dioxole

: 1428859-81-7
(2S,5S)-2-(2’-benzyloxy-(1’S)-hydroxyethyl)-5-(iodomethyl)tetrahydrofuran

Guidance literature:: Multi-step reaction with 5 steps

1.1: ozone; oxygen; sodium hydrogencarbonate / dichloromethane / -78 °C / Inert atmosphere

1.2: -78 - 20 °C / Inert atmosphere

2.1: potassium carbonate; 18-crown-6 ether / tetrahydrofuran / 1 h / Inert atmosphere

2.2: 14 h / Inert atmosphere; Reflux

3.1: lithium aluminium tetrahydride / diethyl ether / 1 h / Inert atmosphere

4.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 2 h / Inert atmosphere

5.1: iodonium dicollidine perchlorate / acetonitrile; water / -10 - 20 °C / Inert atmosphere

With lithium aluminium tetrahydride; 18-crown-6 ether; oxygen; sodium hydride; sodium hydrogencarbonate; potassium carbonate; ozone; In tetrahydrofuran; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; mineral oil; 2.1: |Wittig Olefination / 2.2: |Wittig Olefination;
DOI:10.1021/ol400650v

Reference yield:

: methyl (2S,3S)-2,3-isopropylidendioxy-6-oxohexanoate

: 1428859-81-7
(2S,5S)-2-(2’-benzyloxy-(1’S)-hydroxyethyl)-5-(iodomethyl)tetrahydrofuran

Guidance literature:: Multi-step reaction with 4 steps

1.1: potassium carbonate; 18-crown-6 ether / tetrahydrofuran / 1 h / Inert atmosphere

1.2: 14 h / Inert atmosphere; Reflux

2.1: lithium aluminium tetrahydride / diethyl ether / 1 h / Inert atmosphere

3.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 2 h / Inert atmosphere

4.1: iodonium dicollidine perchlorate / acetonitrile; water / -10 - 20 °C / Inert atmosphere

With lithium aluminium tetrahydride; 18-crown-6 ether; sodium hydride; potassium carbonate; In tetrahydrofuran; diethyl ether; water; N,N-dimethyl-formamide; acetonitrile; mineral oil; 1.1: |Wittig Olefination / 1.2: |Wittig Olefination;
DOI:10.1021/ol400650v