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

Base Information

Chemical Name:(1R,3R)-N-allyloxycarbonyl-1-(4-tert-butyldimethylsiloxymethylphenyl)-3,4-O-isopropylidene-3,4-dihydroxybutylamine
CAS No.:262846-31-1
Molecular Formula:C₂₄H₃₉NO₅Si
Molecular Weight:449.663
Hs Code.:

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

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

Chemical Property:

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

There total 9 articles about (1R,3R)-N-allyloxycarbonyl-1-(4-tert-butyldimethylsiloxymethylphenyl)-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: 90.8%

: 2937-50-0
Allyl chloroformate

: 304655-61-6
(1R,3R)-1-(4-tert-butyldimethylsiloxymethylphenyl)-3,4-O-isopropylidene-3,4-dihydroxybutylazide

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

Guidance literature:: (1R,3R)-1-(4-tert-butyldimethylsiloxymethylphenyl)-3,4-O-isopropylidene-3,4-dihydroxybutylazide; With triphenylphosphine; In tetrahydrofuran; water; at 50 ℃; for 5h;

Allyl chloroformate; With triethylamine; In tetrahydrofuran; at 0 ℃;
DOI:10.1016/S0968-0896(00)00125-5

Reference yield:

: 2937-50-0
Allyl chloroformate

: (R)-1-[4-(tert-Butyl-dimethyl-silanyloxymethyl)-phenyl]-2-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-ethylamine

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

Guidance literature:: With TEA; In tetrahydrofuran; at 0 ℃;
DOI:10.1248/cpb.48.310

Reference yield:

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

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

Guidance literature:: Multi-step reaction with 7 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

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