(2R,3R,5R,6S)-2-(but-3-en-1-yloxy)-6-methyltetrahydro-2H-pyran-3,5-diyl dibenzoate

Base Information

• Chemical Name: (2R,3R,5R,6S)-2-(but-3-en-1-yloxy)-6-methyltetrahydro-2H-pyran-3,5-diyl dibenzoate
• CAS No.: 1084769-85-6
• Molecular Formula: C₂₄H₂₆O₆
• Molecular Weight: 410.467
• Mol file: 1084769-85-6.mol

Synonyms:(2R,3R,5R,6S)-2-(but-3-en-1-yloxy)-6-methyltetrahydro-2H-pyran-3,5-diyl dibenzoate

Chemical Property of (2R,3R,5R,6S)-2-(but-3-en-1-yloxy)-6-methyltetrahydro-2H-pyran-3,5-diyl dibenzoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R,5R,6S)-2-(but-3-en-1-yloxy)-6-methyltetrahydro-2H-pyran-3,5-diyl dibenzoate

There total 1 articles about (2R,3R,5R,6S)-2-(but-3-en-1-yloxy)-6-methyltetrahydro-2H-pyran-3,5-diyl dibenzoate 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: 93.0%

homoalylic alcohol (627-27-0) + (2S,3R,5R)-5-(benzoyloxy)-6-hydroxy-2-methyloxan-3-yl benzoate (168393-80-4) → (2R,3R,5R,6S)-2-(but-3-en-1-yloxy)-6-methyltetrahydro-2H-pyran-3,5-diyl dibenzoate (1084769-85-6)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at 0 ℃; for 2h; Molecular sieve;

DOI:10.1016/j.bmc.2013.07.018

Reference yield: 53.0%

(2R,3R,5R,6S)-2-(but-3-en-1-yloxy)-6-methyltetrahydro-2H-pyran-3,5-diyl dibenzoate (1084769-85-6) + acrylic acid methyl ester (292638-85-8,9003-21-8,96-33-3) → (2R,3R,5R,6S)-2-(((E)-5-methoxy-5-oxopent-3-en-1-yl)oxy)-6-methyltetrahydro-2H-pyran-3,5-diyl dibenzoate (1451476-36-0)

Guidance literature:

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In dichloromethane; stereoselective reaction; Reflux;

DOI:10.1016/j.bmc.2013.07.018

Reference yield:

(2R,3R,5R,6S)-2-(but-3-en-1-yloxy)-6-methyltetrahydro-2H-pyran-3,5-diyl dibenzoate (1084769-85-6) → (2R,3R,5R,6S)-2-((5-methoxy-5-oxopentyl)oxy)-6-methyltetrahydro-2H-pyran-3,5-diyl dibenzoate (1355683-73-6)

Guidance literature:

Multi-step reaction with 2 steps

1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / Reflux

2: hydrogen; palladium 10% on activated carbon / ethyl acetate / 19 h / 23 °C

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; palladium 10% on activated carbon; hydrogen; In dichloromethane; ethyl acetate;

DOI:10.1016/j.bmc.2013.07.018

upstream raw materials:

homoalylic alcohol

(2S,3R,5R)-5-(benzoyloxy)-6-hydroxy-2-methyloxan-3-yl benzoate

Downstream raw materials:

(2R,3R,5R,6S)-2-((5-methoxy-5-oxopentyl)oxy)-6-methyltetrahydro-2H-pyran-3,5-diyl dibenzoate

(2R,3R,5R,6S)-2-(((E)-5-methoxy-5-oxopent-3-en-1-yl)oxy)-6-methyltetrahydro-2H-pyran-3,5-diyl dibenzoate