(1R,3R)-N-allyloxycarbonyl-1-(4-hydroxymethylphenyl)-3,4-O-isopropylidene-3,4-dihydroxybutylamine

Base Information

Chemical Name:(1R,3R)-N-allyloxycarbonyl-1-(4-hydroxymethylphenyl)-3,4-O-isopropylidene-3,4-dihydroxybutylamine
CAS No.:304655-62-7
Molecular Formula:C₁₈H₂₅NO₅
Molecular Weight:335.4
Hs Code.:

Synonyms:(1R,3R)-N-allyloxycarbonyl-1-(4-hydroxymethylphenyl)-3,4-O-isopropylidene-3,4-dihydroxybutylamine

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Chemical Property of (1R,3R)-N-allyloxycarbonyl-1-(4-hydroxymethylphenyl)-3,4-O-isopropylidene-3,4-dihydroxybutylamine

Chemical Property:

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Technology Process of (1R,3R)-N-allyloxycarbonyl-1-(4-hydroxymethylphenyl)-3,4-O-isopropylidene-3,4-dihydroxybutylamine

There total 9 articles about (1R,3R)-N-allyloxycarbonyl-1-(4-hydroxymethylphenyl)-3,4-O-isopropylidene-3,4-dihydroxybutylamine 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: 98.3%

: 262846-31-1
(1R,3R)-N-allyloxycarbonyl-1-(4-tert-butyldimethylsiloxymethylphenyl)-3,4-O-isopropylidene-3,4-dihydroxybutylamine

: 304655-62-7
(1R,3R)-N-allyloxycarbonyl-1-(4-hydroxymethylphenyl)-3,4-O-isopropylidene-3,4-dihydroxybutylamine

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 ℃; for 0.5h;
DOI:10.1016/S0968-0896(00)00125-5

Reference yield:

: 72496-37-8
((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-acetaldehyde

: 304655-62-7
(1R,3R)-N-allyloxycarbonyl-1-(4-hydroxymethylphenyl)-3,4-O-isopropylidene-3,4-dihydroxybutylamine

Guidance literature:: Multi-step reaction with 8 steps

1: 88 percent / n-BuLi / tetrahydrofuran / -70 °C

2: 88 percent / tetrapropylammonium perruthenate; 4-methylmorpholine / CH₂Cl₂

3: NaBH₄ / methanol / 0 °C

4: TEA / CH₂Cl₂ / 0 °C

5: NaN₃ / dimethylformamide / 50 °C

6: PPh₃; water / tetrahydrofuran / 20 °C

7: TEA / tetrahydrofuran / 0 °C

8: n-Bu₄NF / tetrahydrofuran / 0 °C

With 4-methyl-morpholine; sodium tetrahydroborate; n-butyllithium; sodium azide; tetrapropylammonium perruthennate; TEA; tetrabutyl ammonium fluoride; water; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1248/cpb.48.310

Reference yield:

: 228267-27-4
(3R)-1-(4-tert-butyldimethylsiloxymethylphenyl)-3,4-O-isopropylidene-3,4-dihydroxybutanol

: 304655-62-7
(1R,3R)-N-allyloxycarbonyl-1-(4-hydroxymethylphenyl)-3,4-O-isopropylidene-3,4-dihydroxybutylamine

Guidance literature:: Multi-step reaction with 7 steps

1: 88 percent / tetrapropylammonium perruthenate; 4-methylmorpholine / CH₂Cl₂

2: NaBH₄ / methanol / 0 °C

3: TEA / CH₂Cl₂ / 0 °C

4: NaN₃ / dimethylformamide / 50 °C

5: PPh₃; water / tetrahydrofuran / 20 °C

6: TEA / tetrahydrofuran / 0 °C

7: n-Bu₄NF / tetrahydrofuran / 0 °C

With 4-methyl-morpholine; sodium tetrahydroborate; sodium azide; tetrapropylammonium perruthennate; TEA; tetrabutyl ammonium fluoride; water; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1248/cpb.48.310