(S)-N-allyl-N-benzyl-1-((3aR,5R,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)but-3-en-1-amine

Base Information

Chemical Name:(S)-N-allyl-N-benzyl-1-((3aR,5R,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)but-3-en-1-amine
CAS No.:760974-20-7
Molecular Formula:C₂₈H₃₅NO₄
Molecular Weight:449.59
Hs Code.:

Synonyms:(S)-N-allyl-N-benzyl-1-((3aR,5R,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)but-3-en-1-amine

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Chemical Property of (S)-N-allyl-N-benzyl-1-((3aR,5R,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)but-3-en-1-amine

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Technology Process of (S)-N-allyl-N-benzyl-1-((3aR,5R,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)but-3-en-1-amine

There total 3 articles about (S)-N-allyl-N-benzyl-1-((3aR,5R,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)but-3-en-1-amine 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%

: 106-95-6
allyl bromide

: 690981-80-7
(S)-N-benzyl-1-((3aR,5R,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)but-3-en-1-amine

: 760974-20-7
(S)-N-allyl-N-benzyl-1-((3aR,5R,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)but-3-en-1-amine

Guidance literature:: (S)-N-benzyl-1-((3aR,5R,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)but-3-en-1-amine; With sodium hydride; In N,N-dimethyl-formamide; for 0.5h;

allyl bromide; In N,N-dimethyl-formamide; at 20 ℃; for 12h;
DOI:10.1016/j.tetasy.2009.03.038

Reference yield:

: 162740-21-8,191997-36-1
(Z)-N-benzyl-(3-O-benzyl-1,2-O-isopropylidene-α-D-xylofuranos-5-ylidene)amine N-oxide

: 760974-20-7
(S)-N-allyl-N-benzyl-1-((3aR,5R,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)but-3-en-1-amine

Guidance literature:: Multi-step reaction with 3 steps

1: 13 percent / TMSOTf / tetrahydrofuran / 2 h / -78 °C

2: 80 percent / Zn; Cu(OAc)2 / acetic acid / 1 h / 70 °C

3: 71 percent / K₂CO₃ / dimethylformamide / 18 h / 25 °C

With copper diacetate; trimethylsilyl trifluoromethanesulfonate; potassium carbonate; zinc; In tetrahydrofuran; acetic acid; N,N-dimethyl-formamide;
DOI:10.1055/s-2004-829538

Reference yield:

: 690981-78-3
3-O-benzyl-1,2-O-isopropylidene-5,6,7,8-tetradeoxy-5-(N-benzyl-N-hydroxyamino)-β-L-ido-7-eno-octo-1,4-furanose

: 760974-20-7
(S)-N-allyl-N-benzyl-1-((3aR,5R,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)but-3-en-1-amine

Guidance literature:: Multi-step reaction with 2 steps

1: 80 percent / Zn; Cu(OAc)2 / acetic acid / 1 h / 70 °C

2: 71 percent / K₂CO₃ / dimethylformamide / 18 h / 25 °C

With copper diacetate; potassium carbonate; zinc; In acetic acid; N,N-dimethyl-formamide;
DOI:10.1055/s-2004-829538