(1S,2R,6R,4Z)-5-(3'-(benzyloxy)propyl)-1,2,4-trimethyl-3,9-dioxabicyclo<4.2.1>non-4-ene

Base Information

Chemical Name:(1S,2R,6R,4Z)-5-(3'-(benzyloxy)propyl)-1,2,4-trimethyl-3,9-dioxabicyclo<4.2.1>non-4-ene
CAS No.:128329-77-1
Molecular Formula:C₂₀H₂₈O₃
Molecular Weight:316.441
Hs Code.:

Synonyms:(1S,2R,6R,4Z)-5-(3'-(benzyloxy)propyl)-1,2,4-trimethyl-3,9-dioxabicyclo<4.2.1>non-4-ene

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Chemical Property of (1S,2R,6R,4Z)-5-(3'-(benzyloxy)propyl)-1,2,4-trimethyl-3,9-dioxabicyclo<4.2.1>non-4-ene

Chemical Property:

Purity/Quality:

Safty Information:

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Hazard Codes:

MSDS Files:: SDS file from LookChem

Useful:

Technology Process of (1S,2R,6R,4Z)-5-(3'-(benzyloxy)propyl)-1,2,4-trimethyl-3,9-dioxabicyclo<4.2.1>non-4-ene

There total 2 articles about (1S,2R,6R,4Z)-5-(3'-(benzyloxy)propyl)-1,2,4-trimethyl-3,9-dioxabicyclo<4.2.1>non-4-ene 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:

: 128440-50-6
(1S,2R,5S,6R)-5-(3'-(benzyloxy)propyl)-1,2-dimethyl-3,9-dioxabicyclo<4.2.1>nonan-4-one

: 128329-77-1
(1S,2R,6R,4Z)-5-(3'-(benzyloxy)propyl)-1,2,4-trimethyl-3,9-dioxabicyclo<4.2.1>non-4-ene

Guidance literature:: Multi-step reaction with 2 steps

1: 94 percent / pyridine / tetrahydrofuran; toluene / 1.) -45 deg C, 40 min, 2.) 20 deg C, 45 min

2: 100 percent / pyridinium tosylate / CH₂Cl₂ / 6 h / 20 °C

With pyridine; pyridinium p-toluenesulfonate; In tetrahydrofuran; dichloromethane; toluene;
DOI:10.1021/ja00169a042

Reference yield:

: 128329-75-9
(+)-(4S)-3-<5-(benzyloxy)-(2S)-<(2R,5S)-5-methyl-5-<(1R)-1-hydroxyethyl>tetrahydrofuranyl>pentanoyl>-4-isopropyl-1,3-oxazolidin-2-one

: 128329-77-1
(1S,2R,6R,4Z)-5-(3'-(benzyloxy)propyl)-1,2,4-trimethyl-3,9-dioxabicyclo<4.2.1>non-4-ene

Guidance literature:: Multi-step reaction with 3 steps

1: 1.) PhMgBr, 2.) LiBr / 1.) THF, -78 deg C, 2 h, 2.) 20 deg C, 24 h

2: 94 percent / pyridine / tetrahydrofuran; toluene / 1.) -45 deg C, 40 min, 2.) 20 deg C, 45 min

3: 100 percent / pyridinium tosylate / CH₂Cl₂ / 6 h / 20 °C

With pyridine; pyridinium p-toluenesulfonate; phenylmagnesium bromide; lithium bromide; In tetrahydrofuran; dichloromethane; toluene;
DOI:10.1021/ja00169a042

Reference yield:

: 128329-77-1
(1S,2R,6R,4Z)-5-(3'-(benzyloxy)propyl)-1,2,4-trimethyl-3,9-dioxabicyclo<4.2.1>non-4-ene

: 128329-84-0
(Z)-(S)-6-[(4S,5S,6R)-6-((R)-2-Benzyloxy-1-methyl-ethyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-2-[(2R,5S)-5-((R)-1-hydroxy-ethyl)-5-methyl-tetrahydro-furan-2-yl]-hex-5-en-2-ol

Guidance literature:: Multi-step reaction with 9 steps

1: 1.) ozone, 2.) dimethyl sulfide / 1.) CH₂Cl₂, -78 deg C, 2a.) -78 deg C, 1 h, 2b.) 20 deg C, 1 h

2: 55 percent / CH₂Cl₂; diethyl ether / 1.) -78 deg C, 8 h, 2.) 20 deg C, 2 h

3: 94 percent / triethylamine / CH₂Cl₂ / 2 h / 0 °C

4: 100 percent / H₂ / 10percent Pd/C / ethyl acetate / 19 h / 20 °C / 3040 Torr

5: 1.88 g / triethylamine / CH₂Cl₂ / 3 h / 0 °C

6: 1.84 g / NaI, NaHCO₃, diisopropylethylamine / acetone / 18 h / 20 °C

7: 78 percent / diisopropylethylamine / toluene; acetonitrile / 54 h / 75 °C

8: 1.) sodium bis(trimethylsilyl)amide / 1.) toluene, 20 deg C, 15 min, 2a.) -78 deg C, 15 min, 2b.) 20 deg C, 30 min

9: 94 percent / Bu₄NF / tetrahydrofuran / 36 h / 80 °C

With dimethylsulfide; tetrabutyl ammonium fluoride; hydrogen; sodium hexamethyldisilazane; sodium hydrogencarbonate; ozone; triethylamine; N-ethyl-N,N-diisopropylamine; sodium iodide; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; dichloromethane; ethyl acetate; acetone; toluene; acetonitrile;
DOI:10.1021/ja00169a042