(2S,3R,5R,6R)-2-methyl-6-((R)-pent-4-en-2-yloxy)tetrahydro-2H-pyran-3,5-diyl dibenzoate

Base Information

Chemical Name:(2S,3R,5R,6R)-2-methyl-6-((R)-pent-4-en-2-yloxy)tetrahydro-2H-pyran-3,5-diyl dibenzoate
CAS No.:1451475-78-7
Molecular Formula:C₂₅H₂₈O₆
Molecular Weight:424.494
Hs Code.:

Synonyms:(2S,3R,5R,6R)-2-methyl-6-((R)-pent-4-en-2-yloxy)tetrahydro-2H-pyran-3,5-diyl dibenzoate

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Chemical Property of (2S,3R,5R,6R)-2-methyl-6-((R)-pent-4-en-2-yloxy)tetrahydro-2H-pyran-3,5-diyl dibenzoate

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Technology Process of (2S,3R,5R,6R)-2-methyl-6-((R)-pent-4-en-2-yloxy)tetrahydro-2H-pyran-3,5-diyl dibenzoate

There total 3 articles about (2S,3R,5R,6R)-2-methyl-6-((R)-pent-4-en-2-yloxy)tetrahydro-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: 85.0%

: 64584-92-5
(R)-pent-4-en-2-ol

: 168170-58-9
(3’R,5’R-dibenzoyloxy-6’S-methyl-(2H)-tetrahydropyran-2-yloxy)-1-(2,2,2-trichloroacetimide)

: 1451475-78-7
(2S,3R,5R,6R)-2-methyl-6-((R)-pent-4-en-2-yloxy)tetrahydro-2H-pyran-3,5-diyl dibenzoate

Guidance literature:: With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at 0 - 20 ℃; for 4h;
DOI:10.1039/d0ob00799d

Reference yield: 73.0%

: 64584-92-5
(R)-pent-4-en-2-ol

: 168393-80-4
(2S,3R,5R)-5-(benzoyloxy)-6-hydroxy-2-methyloxan-3-yl benzoate

: 1451475-78-7
(2S,3R,5R,6R)-2-methyl-6-((R)-pent-4-en-2-yloxy)tetrahydro-2H-pyran-3,5-diyl dibenzoate

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:

: 104768-13-0
(2R,3R,5R,6S)-2-hydroxy-6-methyltetrahydro-2H-pyran-3,5-diyl dibenzoate

: 1451475-78-7
(2S,3R,5R,6R)-2-methyl-6-((R)-pent-4-en-2-yloxy)tetrahydro-2H-pyran-3,5-diyl dibenzoate

Guidance literature:: Multi-step reaction with 2 steps

1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 0.5 h / 20 °C

2: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 4 h / 0 - 20 °C

With trimethylsilyl trifluoromethanesulfonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; 2: |Grubbs Olefin Metathesis;
DOI:10.1039/d0ob00799d