<1S-(1α,4α,5α)>-3-<(Benzyloxy)methyl>-4,5-(isopropylidenedioxy)-1-<(4-methoxybenzyl)oxy>-2-cyclopentene

Base Information

Chemical Name:<1S-(1α,4α,5α)>-3-<(Benzyloxy)methyl>-4,5-(isopropylidenedioxy)-1-<(4-methoxybenzyl)oxy>-2-cyclopentene
CAS No.:160343-89-5
Molecular Formula:C₂₄H₂₈O₅
Molecular Weight:396.483
Hs Code.:

Synonyms:<1S-(1α,4α,5α)>-3-<(Benzyloxy)methyl>-4,5-(isopropylidenedioxy)-1-<(4-methoxybenzyl)oxy>-2-cyclopentene

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Chemical Property of <1S-(1α,4α,5α)>-3-<(Benzyloxy)methyl>-4,5-(isopropylidenedioxy)-1-<(4-methoxybenzyl)oxy>-2-cyclopentene

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Technology Process of <1S-(1α,4α,5α)>-3-<(Benzyloxy)methyl>-4,5-(isopropylidenedioxy)-1-<(4-methoxybenzyl)oxy>-2-cyclopentene

There total 8 articles about <1S-(1α,4α,5α)>-3-<(Benzyloxy)methyl>-4,5-(isopropylidenedioxy)-1-<(4-methoxybenzyl)oxy>-2-cyclopentene 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: 100.0%

: 100-39-0
benzyl bromide

: 160343-88-4
<1S-(1α,4α,5α)>-3-(Hydroxymethyl)-4,5-(isopropylidenedioxy)-1-<(4-methoxybenzyl)oxy>-2-cyclopentene

: 160343-89-5
<1S-(1α,4α,5α)>-3-<(Benzyloxy)methyl>-4,5-(isopropylidenedioxy)-1-<(4-methoxybenzyl)oxy>-2-cyclopentene

Guidance literature:: With sodium hydride; In N,N-dimethyl-formamide; at 24 ℃; for 2h;
DOI:10.1016/S0040-4039(00)75990-9

Reference yield:

: 5336-08-3
D-Ribono-1,4-lactone

: 160343-89-5
<1S-(1α,4α,5α)>-3-<(Benzyloxy)methyl>-4,5-(isopropylidenedioxy)-1-<(4-methoxybenzyl)oxy>-2-cyclopentene

Guidance literature:: Multi-step reaction with 8 steps

1: 2.) 1 M aq. HCl / 1.) pyridinium p-toluenesulfonate / 1.) 50 deg C, 1 h, 2.) THF, 24 - 25 deg C, 1 h

2: 95 percent / Dess-Martin reagent / CH₂Cl₂ / 0.5 h / Ambient temperature

3: 43 percent / DABCO / dimethylformamide / 1 h

5: 99 percent / CeCl₃*7H₂O, NaBH₄ / ethanol / 0.5 h / Ambient temperature

6: 69 percent / NaH / dimethylformamide; paraffin / 3 h / Ambient temperature

7: 93 percent / n-Bu₄NF / tetrahydrofuran / 3 h / Ambient temperature

8: 100 percent / NaH / dimethylformamide; paraffin / 2 h / Ambient temperature

With 1,4-diaza-bicyclo[2.2.2]octane; hydrogenchloride; sodium tetrahydroborate; cerium(III) chloride; tetrabutyl ammonium fluoride; sodium hydride; Dess-Martin periodane; pyridinium p-toluenesulfonate; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide; paraffin;
DOI:10.1021/jo00095a021

Reference yield:

: 30725-00-9
2,3-O-isopropylidene-D-ribonic-γ-lactone

: 160343-89-5
<1S-(1α,4α,5α)>-3-<(Benzyloxy)methyl>-4,5-(isopropylidenedioxy)-1-<(4-methoxybenzyl)oxy>-2-cyclopentene

Guidance literature:: Multi-step reaction with 7 steps

1: 95 percent / Dess-Martin reagent / CH₂Cl₂ / 0.5 h / Ambient temperature

2: 43 percent / DABCO / dimethylformamide / 1 h

4: 99 percent / CeCl₃*7H₂O, NaBH₄ / ethanol / 0.5 h / Ambient temperature

5: 69 percent / NaH / dimethylformamide; paraffin / 3 h / Ambient temperature

6: 93 percent / n-Bu₄NF / tetrahydrofuran / 3 h / Ambient temperature

7: 100 percent / NaH / dimethylformamide; paraffin / 2 h / Ambient temperature

With 1,4-diaza-bicyclo[2.2.2]octane; sodium tetrahydroborate; cerium(III) chloride; tetrabutyl ammonium fluoride; sodium hydride; Dess-Martin periodane; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide; paraffin;
DOI:10.1021/jo00095a021