(1R,3S,4R,5R)-3-[(E/Z)-1-benzyloxymethyl-3-hydroxy-1-propenyl]-4-methyl-7,7-dimethyl-2,6,8-trioxabicyclo[3.3.0]octane

Base Information

Chemical Name:(1R,3S,4R,5R)-3-[(E/Z)-1-benzyloxymethyl-3-hydroxy-1-propenyl]-4-methyl-7,7-dimethyl-2,6,8-trioxabicyclo[3.3.0]octane
CAS No.:184964-73-6
Molecular Formula:C₁₉H₂₆O₅
Molecular Weight:334.412
Hs Code.:

Synonyms:(1R,3S,4R,5R)-3-[(E/Z)-1-benzyloxymethyl-3-hydroxy-1-propenyl]-4-methyl-7,7-dimethyl-2,6,8-trioxabicyclo[3.3.0]octane

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Chemical Property of (1R,3S,4R,5R)-3-[(E/Z)-1-benzyloxymethyl-3-hydroxy-1-propenyl]-4-methyl-7,7-dimethyl-2,6,8-trioxabicyclo[3.3.0]octane

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Technology Process of (1R,3S,4R,5R)-3-[(E/Z)-1-benzyloxymethyl-3-hydroxy-1-propenyl]-4-methyl-7,7-dimethyl-2,6,8-trioxabicyclo[3.3.0]octane

There total 6 articles about (1R,3S,4R,5R)-3-[(E/Z)-1-benzyloxymethyl-3-hydroxy-1-propenyl]-4-methyl-7,7-dimethyl-2,6,8-trioxabicyclo[3.3.0]octane 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: 90.0%

: 184964-71-4
(1R,3S,4R,5R)-3-[(E/Z)-1-benzyloxymethyl-2-ethoxycarbonylethenyl]-4-methyl-7,7-dimethyl-2,6,8-trioxabicyclo[3.3.0]octane

: 184964-73-6
(1R,3S,4R,5R)-3-[(E/Z)-1-benzyloxymethyl-3-hydroxy-1-propenyl]-4-methyl-7,7-dimethyl-2,6,8-trioxabicyclo[3.3.0]octane

Guidance literature:: With diisobutylaluminium hydride; In dichloromethane; at -15 ℃;
DOI:10.1039/c39950000793

Reference yield:

: 26291-75-8,81114-49-0,109200-09-1,128461-80-3
(R)-1-((3aR,5S,6R,6aR)-2,2,6-trimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl)ethane-1,2-diol

: 184964-73-6
(1R,3S,4R,5R)-3-[(E/Z)-1-benzyloxymethyl-3-hydroxy-1-propenyl]-4-methyl-7,7-dimethyl-2,6,8-trioxabicyclo[3.3.0]octane

Guidance literature:: Multi-step reaction with 4 steps

1.1: di-n-butyltin oxide / toluene / 3 h / Heating

1.2: 66 percent / cesium fluoride / dimethylformamide / 18 h / 20 °C

2.1: CrO₃; aq. sulfuric acid / acetone / 1 h / 0 °C

3.1: toluene / 16 h / 20 - 60 °C

4.1: 90 percent / diisobutylaluminum hydride / CH₂Cl₂ / 0.5 h / -15 °C

With chromium(VI) oxide; sulfuric acid; diisobutylaluminium hydride; di(n-butyl)tin oxide; In dichloromethane; acetone; toluene; 1.1: stannylation / 1.2: Alkylation / 2.1: Jones oxidation / 3.1: Wittig reaction / 4.1: Reduction;
DOI:10.1016/S0040-4020(97)01015-6

Reference yield:

: 114144-67-1
6-O-benzyl-3-deoxy-1,2-O-isopropylidene-3-C-methyl-α-D-allofuranose

: 184964-73-6
(1R,3S,4R,5R)-3-[(E/Z)-1-benzyloxymethyl-3-hydroxy-1-propenyl]-4-methyl-7,7-dimethyl-2,6,8-trioxabicyclo[3.3.0]octane

Guidance literature:: Multi-step reaction with 3 steps

1: CrO₃; aq. sulfuric acid / acetone / 1 h / 0 °C

2: toluene / 16 h / 20 - 60 °C

3: 90 percent / diisobutylaluminum hydride / CH₂Cl₂ / 0.5 h / -15 °C

With chromium(VI) oxide; sulfuric acid; diisobutylaluminium hydride; In dichloromethane; acetone; toluene; 1: Jones oxidation / 2: Wittig reaction / 3: Reduction;
DOI:10.1016/S0040-4020(97)01015-6