(2R,3S,5R,6S)-3,5-bis(benzyloxy)-2-((R)-hex-5-en-2-yloxy)-6-methyltetrahydro-2H-pyran

Base Information

Chemical Name:(2R,3S,5R,6S)-3,5-bis(benzyloxy)-2-((R)-hex-5-en-2-yloxy)-6-methyltetrahydro-2H-pyran
CAS No.:1417721-62-0
Molecular Formula:C₂₆H₃₄O₄
Molecular Weight:410.554
Hs Code.:

Synonyms:(2R,3S,5R,6S)-3,5-bis(benzyloxy)-2-((R)-hex-5-en-2-yloxy)-6-methyltetrahydro-2H-pyran

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Chemical Property of (2R,3S,5R,6S)-3,5-bis(benzyloxy)-2-((R)-hex-5-en-2-yloxy)-6-methyltetrahydro-2H-pyran

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Technology Process of (2R,3S,5R,6S)-3,5-bis(benzyloxy)-2-((R)-hex-5-en-2-yloxy)-6-methyltetrahydro-2H-pyran

There total 5 articles about (2R,3S,5R,6S)-3,5-bis(benzyloxy)-2-((R)-hex-5-en-2-yloxy)-6-methyltetrahydro-2H-pyran 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%

: 1417721-61-9
C₁₂H₂₂O₄

: 100-39-0
benzyl bromide

: 1417721-62-0
(2R,3S,5R,6S)-3,5-bis(benzyloxy)-2-((R)-hex-5-en-2-yloxy)-6-methyltetrahydro-2H-pyran

Guidance literature:: C₁₂H₂₂O₄; With sodium hydride; In N,N-dimethyl-formamide; mineral oil; at 0 ℃; for 0.333333h;

benzyl bromide; In N,N-dimethyl-formamide; mineral oil;
DOI:10.1002/anie.201206797

Reference yield:

: 1417721-60-8
(2S,3R,5S,6R)-6-((R)-hex-5-en-2-yloxy)-5-hydroxy-2-methyltetrahydro-2H-pyran-3-yl benzoate

: 1417721-62-0
(2R,3S,5R,6S)-3,5-bis(benzyloxy)-2-((R)-hex-5-en-2-yloxy)-6-methyltetrahydro-2H-pyran

Guidance literature:: Multi-step reaction with 2 steps

1: lithium hydroxide / tetrahydrofuran; water; 1,4-dioxane / 3 h / 60 °C

2: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.33 h / 0 °C

With sodium hydride; lithium hydroxide; In tetrahydrofuran; 1,4-dioxane; water; N,N-dimethyl-formamide; mineral oil;
DOI:10.1002/anie.201206797

Reference yield:

: 1172590-11-2
(2R,3R,5R,6S)-2-((R)-hex-5-en-2-yloxy)-6-methyltetrahydro-2H-pyran-3,5-diyl dibenzoate

: 1417721-62-0
(2R,3S,5R,6S)-3,5-bis(benzyloxy)-2-((R)-hex-5-en-2-yloxy)-6-methyltetrahydro-2H-pyran

Guidance literature:: Multi-step reaction with 5 steps

1: lithium hydroxide / tetrahydrofuran; water; 1,4-dioxane / 0.67 h / 60 °C

2: Dess-Martin periodane / dichloromethane / 5 h

3: sodium tetrahydroborate / methanol; dichloromethane / 0.17 h

4: lithium hydroxide / tetrahydrofuran; water; 1,4-dioxane / 3 h / 60 °C

5: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.33 h / 0 °C

With sodium tetrahydroborate; sodium hydride; Dess-Martin periodane; lithium hydroxide; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; N,N-dimethyl-formamide; mineral oil;
DOI:10.1002/anie.201206797