(2R,3S,4R)-3,4-bis(benzyloxy)-2-((Z)-but-1-en-1-yl)-5-methoxytetrahydrofuran

Base Information

Chemical Name:(2R,3S,4R)-3,4-bis(benzyloxy)-2-((Z)-but-1-en-1-yl)-5-methoxytetrahydrofuran
CAS No.:1428859-97-5
Molecular Formula:C₂₃H₂₈O₄
Molecular Weight:368.473
Hs Code.:

Synonyms:(2R,3S,4R)-3,4-bis(benzyloxy)-2-((Z)-but-1-en-1-yl)-5-methoxytetrahydrofuran

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Chemical Property of (2R,3S,4R)-3,4-bis(benzyloxy)-2-((Z)-but-1-en-1-yl)-5-methoxytetrahydrofuran

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Technology Process of (2R,3S,4R)-3,4-bis(benzyloxy)-2-((Z)-but-1-en-1-yl)-5-methoxytetrahydrofuran

There total 7 articles about (2R,3S,4R)-3,4-bis(benzyloxy)-2-((Z)-but-1-en-1-yl)-5-methoxytetrahydrofuran 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:

: 1428859-96-4
C₁₆H₂₂O₄

: 100-39-0
benzyl bromide

: 1428859-97-5
(2R,3S,4R)-3,4-bis(benzyloxy)-2-((Z)-but-1-en-1-yl)-5-methoxytetrahydrofuran

Guidance literature:: C₁₆H₂₂O₄; With sodium hydride; In tetrahydrofuran; mineral oil; at 0 - 65 ℃; for 0.75h;

benzyl bromide; at 65 ℃; for 7h;
DOI:10.1021/ol400528g

Reference yield:

: 100-39-0
benzyl bromide

: 1428859-97-5
(2R,3S,4R)-3,4-bis(benzyloxy)-2-((Z)-but-1-en-1-yl)-5-methoxytetrahydrofuran

Guidance literature:: Multi-step reaction with 6 steps

1.1: sodium hydride; tetra-(n-butyl)ammonium iodide / tetrahydrofuran / 10 h / 70 °C

2.1: acetic acid / water / 5 h / 55 °C

3.1: sodium periodate / water; methanol / 0.75 h

4.1: n-butyllithium / tetrahydrofuran / 20 h / -78 - 20 °C

5.1: hydrogenchloride / water; methanol / 5 h / 20 °C

6.1: sodium hydride / tetrahydrofuran; mineral oil / 0.75 h / 0 - 65 °C

6.2: 7 h / 65 °C

With hydrogenchloride; sodium periodate; n-butyllithium; tetra-(n-butyl)ammonium iodide; sodium hydride; acetic acid; In tetrahydrofuran; methanol; water; mineral oil; 4.1: |Wittig Olefination;
DOI:10.1021/ol400528g

Reference yield:

: 98760-37-3
(3aR,5R,6S,6aR)-6-(benzyloxy)-5-((Z)-but-1-en-1-yl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole

: 1428859-97-5
(2R,3S,4R)-3,4-bis(benzyloxy)-2-((Z)-but-1-en-1-yl)-5-methoxytetrahydrofuran

Guidance literature:: Multi-step reaction with 2 steps

1.1: hydrogenchloride / water; methanol / 5 h / 20 °C

2.1: sodium hydride / tetrahydrofuran; mineral oil / 0.75 h / 0 - 65 °C

2.2: 7 h / 65 °C

With hydrogenchloride; sodium hydride; In tetrahydrofuran; methanol; water; mineral oil;
DOI:10.1021/ol400528g