<1R-(1α,2β,3β,4β,5β)>-5-Azido-1-(benzyloxy)-1-<(benzyloxy)methyl>-2,3-(isopropylidenedioxy)-4-<(4-methoxybenzyl)oxy>cyclopentane

Base Information

Chemical Name:<1R-(1α,2β,3β,4β,5β)>-5-Azido-1-(benzyloxy)-1-<(benzyloxy)methyl>-2,3-(isopropylidenedioxy)-4-<(4-methoxybenzyl)oxy>cyclopentane
CAS No.:160343-99-7
Molecular Formula:C₃₁H₃₅N₃O₆
Molecular Weight:545.635
Hs Code.:

Synonyms:<1R-(1α,2β,3β,4β,5β)>-5-Azido-1-(benzyloxy)-1-<(benzyloxy)methyl>-2,3-(isopropylidenedioxy)-4-<(4-methoxybenzyl)oxy>cyclopentane

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Chemical Property of <1R-(1α,2β,3β,4β,5β)>-5-Azido-1-(benzyloxy)-1-<(benzyloxy)methyl>-2,3-(isopropylidenedioxy)-4-<(4-methoxybenzyl)oxy>cyclopentane

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Technology Process of <1R-(1α,2β,3β,4β,5β)>-5-Azido-1-(benzyloxy)-1-<(benzyloxy)methyl>-2,3-(isopropylidenedioxy)-4-<(4-methoxybenzyl)oxy>cyclopentane

There total 14 articles about <1R-(1α,2β,3β,4β,5β)>-5-Azido-1-(benzyloxy)-1-<(benzyloxy)methyl>-2,3-(isopropylidenedioxy)-4-<(4-methoxybenzyl)oxy>cyclopentane 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: 89.0%

: 100-39-0
benzyl bromide

: 160343-98-6
<1R-(1α,2β,3β,4β,5β)>-5-Azido-1-(hydroxymethyl)-2,3-(isopropylidenedioxy)-4-<(4-methoxybenzyl)oxy>cyclopentan-1-ol

: 160343-99-7
<1R-(1α,2β,3β,4β,5β)>-5-Azido-1-(benzyloxy)-1-<(benzyloxy)methyl>-2,3-(isopropylidenedioxy)-4-<(4-methoxybenzyl)oxy>cyclopentane

Guidance literature:: With sodium hydride; In N,N-dimethyl-formamide; paraffin; at 10 ℃; for 16h;
DOI:10.1021/jo00095a021

Reference yield:

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

: 160343-99-7
<1R-(1α,2β,3β,4β,5β)>-5-Azido-1-(benzyloxy)-1-<(benzyloxy)methyl>-2,3-(isopropylidenedioxy)-4-<(4-methoxybenzyl)oxy>cyclopentane

Guidance literature:: Multi-step reaction with 12 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: 84 percent / DMAP / CH₂Cl₂ / 1.) 0 deg C, 1 h, 2.) r.t., 30 min

6: 89 percent / 85percent m-chloroperoxybenzoic acid / CHCl₃ / 96 h / Ambient temperature

7: 100 percent / H₂ / 10percent Pd/C / ethyl acetate / 0.5 h / Ambient temperature

8: 92 percent / NaN₃, NH₄Cl / dimethylformamide / 16 h / 100 °C

9: 82 percent / p-TsOH*H₂O / dimethylformamide / 16 h / Ambient temperature

10: 90 percent / NaH / dimethylformamide; tetrahydrofuran; paraffin / 16 h / Ambient temperature

11: 64 percent / 85percent aq. AcOH / 24 h / 40 - 45 °C

12: 89 percent / NaH / dimethylformamide; paraffin / 16 h / 10 °C

With 1,4-diaza-bicyclo[2.2.2]octane; dmap; sodium tetrahydroborate; sodium azide; cerium(III) chloride; hydrogen; sodium hydride; ammonium chloride; Dess-Martin periodane; toluene-4-sulfonic acid; acetic acid; 3-chloro-benzenecarboperoxoic acid; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; chloroform; ethyl acetate; N,N-dimethyl-formamide; paraffin;
DOI:10.1021/jo00095a021

Reference yield:

: 160343-79-3
(3aS,4S,6aR)-6-{{[(1,1-dimethylethyl)dimethylsilyl]oxy}methyl}-3a,6a-dihydro-2,2-dimethyl-4H-cyclopenta[d]-1,3-dioxol-4-ol

: 160343-99-7
<1R-(1α,2β,3β,4β,5β)>-5-Azido-1-(benzyloxy)-1-<(benzyloxy)methyl>-2,3-(isopropylidenedioxy)-4-<(4-methoxybenzyl)oxy>cyclopentane

Guidance literature:: Multi-step reaction with 8 steps

1: 84 percent / DMAP / CH₂Cl₂ / 1.) 0 deg C, 1 h, 2.) r.t., 30 min

2: 89 percent / 85percent m-chloroperoxybenzoic acid / CHCl₃ / 96 h / Ambient temperature

3: 100 percent / H₂ / 10percent Pd/C / ethyl acetate / 0.5 h / Ambient temperature

4: 92 percent / NaN₃, NH₄Cl / dimethylformamide / 16 h / 100 °C

5: 82 percent / p-TsOH*H₂O / dimethylformamide / 16 h / Ambient temperature

6: 90 percent / NaH / dimethylformamide; tetrahydrofuran; paraffin / 16 h / Ambient temperature

7: 64 percent / 85percent aq. AcOH / 24 h / 40 - 45 °C

8: 89 percent / NaH / dimethylformamide; paraffin / 16 h / 10 °C

With dmap; sodium azide; hydrogen; sodium hydride; ammonium chloride; toluene-4-sulfonic acid; acetic acid; 3-chloro-benzenecarboperoxoic acid; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; chloroform; ethyl acetate; N,N-dimethyl-formamide; paraffin;
DOI:10.1021/jo00095a021