<3R,5R,5(1S)>-N-Benzyl-5-<1-(benzyloxy)pentyl>-3-<<(p-tolylsulfonyl)oxy>-methyl>isoxazolidine

Base Information

Chemical Name:<3R,5R,5(1S)>-N-Benzyl-5-<1-(benzyloxy)pentyl>-3-<<(p-tolylsulfonyl)oxy>-methyl>isoxazolidine
CAS No.:138890-23-0
Molecular Formula:C₃₀H₃₇NO₅S
Molecular Weight:523.693
Hs Code.:

Synonyms:<3R,5R,5(1S)>-N-Benzyl-5-<1-(benzyloxy)pentyl>-3-<<(p-tolylsulfonyl)oxy>-methyl>isoxazolidine

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Chemical Property of <3R,5R,5(1S)>-N-Benzyl-5-<1-(benzyloxy)pentyl>-3-<<(p-tolylsulfonyl)oxy>-methyl>isoxazolidine

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Technology Process of <3R,5R,5(1S)>-N-Benzyl-5-<1-(benzyloxy)pentyl>-3-<<(p-tolylsulfonyl)oxy>-methyl>isoxazolidine

There total 9 articles about <3R,5R,5(1S)>-N-Benzyl-5-<1-(benzyloxy)pentyl>-3-<<(p-tolylsulfonyl)oxy>-methyl>isoxazolidine 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: 97.0%

: 138890-22-9
<3R,5R,5(1S)>-N-Benzyl-5-<1-(benzyloxy)pentyl>-3-(hydroxymethyl)isoxazolidine

: 98-59-9
p-toluenesulfonyl chloride

: 138890-23-0
<3R,5R,5(1S)>-N-Benzyl-5-<1-(benzyloxy)pentyl>-3-<<(p-tolylsulfonyl)oxy>-methyl>isoxazolidine

Guidance literature:: With dmap; N-ethyl-N,N-diisopropylamine; In dichloromethane; for 1.5h; Ambient temperature;
DOI:10.1016/S0040-4020(01)80881-4

Reference yield:

: 84379-53-3
2-O-benzyl-3,4-O-isopropylidene-L-threitol

: 138890-23-0
<3R,5R,5(1S)>-N-Benzyl-5-<1-(benzyloxy)pentyl>-3-<<(p-tolylsulfonyl)oxy>-methyl>isoxazolidine

Guidance literature:: Multi-step reaction with 8 steps

1: 97 percent / N,N-dimethylaminopyridine / CH₂Cl₂ / 2 h

2: 87 percent / Li₂CuCl₄ / tetrahydrofuran / 1) -78 deg C, 1.5 h, 2) room temp., 65 h

3: 98 percent / 6N HCl / methanol / 1 h / 55 °C

4: 1.5 h / 70 °C

5: acetic anhydride / 1 h / Heating

6: 57 percent / toluene / 14 h / Heating

7: 96 percent / LiAlH₄ / diethyl ether / 14 h / Ambient temperature

8: 97 percent / N,N-dimethylaminopyridine, diisopropylethylamine / CH₂Cl₂ / 1.5 h / Ambient temperature

With hydrogenchloride; dmap; lithium aluminium tetrahydride; dilithium tetrachlorocuprate; acetic anhydride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; toluene;
DOI:10.1016/S0040-4020(01)80881-4

Reference yield:

: 131446-96-3
(S)-2-(benzyloxy)-2-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)ethyl 4-methylbenzenesulfonate

: 138890-23-0
<3R,5R,5(1S)>-N-Benzyl-5-<1-(benzyloxy)pentyl>-3-<<(p-tolylsulfonyl)oxy>-methyl>isoxazolidine

Guidance literature:: Multi-step reaction with 7 steps

1: 87 percent / Li₂CuCl₄ / tetrahydrofuran / 1) -78 deg C, 1.5 h, 2) room temp., 65 h

2: 98 percent / 6N HCl / methanol / 1 h / 55 °C

3: 1.5 h / 70 °C

4: acetic anhydride / 1 h / Heating

5: 57 percent / toluene / 14 h / Heating

6: 96 percent / LiAlH₄ / diethyl ether / 14 h / Ambient temperature

7: 97 percent / N,N-dimethylaminopyridine, diisopropylethylamine / CH₂Cl₂ / 1.5 h / Ambient temperature

With hydrogenchloride; dmap; lithium aluminium tetrahydride; dilithium tetrachlorocuprate; acetic anhydride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; toluene;
DOI:10.1016/S0040-4020(01)80881-4