(3R,3aR,6aR)-3-(tert-butyldiphenylsilyloxymethyl)-N-(tert-butyloxycarbonyl)tetrahydrofuro[2,3-d]isoxazol-5-one

Base Information

Chemical Name:(3R,3aR,6aR)-3-(tert-butyldiphenylsilyloxymethyl)-N-(tert-butyloxycarbonyl)tetrahydrofuro[2,3-d]isoxazol-5-one
CAS No.:420846-38-4
Molecular Formula:C₂₇H₃₅NO₆Si
Molecular Weight:497.663
Hs Code.:

Synonyms:(3R,3aR,6aR)-3-(tert-butyldiphenylsilyloxymethyl)-N-(tert-butyloxycarbonyl)tetrahydrofuro[2,3-d]isoxazol-5-one

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Chemical Property of (3R,3aR,6aR)-3-(tert-butyldiphenylsilyloxymethyl)-N-(tert-butyloxycarbonyl)tetrahydrofuro[2,3-d]isoxazol-5-one

Chemical Property:

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Technology Process of (3R,3aR,6aR)-3-(tert-butyldiphenylsilyloxymethyl)-N-(tert-butyloxycarbonyl)tetrahydrofuro[2,3-d]isoxazol-5-one

There total 5 articles about (3R,3aR,6aR)-3-(tert-butyldiphenylsilyloxymethyl)-N-(tert-butyloxycarbonyl)tetrahydrofuro[2,3-d]isoxazol-5-one 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: 64.0%

: 24424-99-5
di-tert-butyl dicarbonate

: 1053616-43-5
(3R,3aR,6aR)-3-tert-butyldiphenylsilyloxymethyl-N-(2',3':5',6'-di-O-isopropylidene-α-L-gulofuranosyl)tetrahydrofuro[2,3-d]isoxazol-5-one

: 420846-38-4
(3R,3aR,6aR)-3-(tert-butyldiphenylsilyloxymethyl)-N-(tert-butyloxycarbonyl)tetrahydrofuro[2,3-d]isoxazol-5-one

Guidance literature:: (3R,3aR,6aR)-3-tert-butyldiphenylsilyloxymethyl-N-(2',3':5',6'-di-O-isopropylidene-α-L-gulofuranosyl)tetrahydrofuro[2,3-d]isoxazol-5-one; With perchloric acid; In acetonitrile; at 20 ℃; for 5h;

di-tert-butyl dicarbonate; With sodium hydrogencarbonate; In acetonitrile;
DOI:10.1039/c1ob06067h

Reference yield:

: 115869-43-7
(tert-butyldiphenylsilanyloxy)acetaldehyde

: 420846-38-4
(3R,3aR,6aR)-3-(tert-butyldiphenylsilyloxymethyl)-N-(tert-butyloxycarbonyl)tetrahydrofuro[2,3-d]isoxazol-5-one

Guidance literature:: Multi-step reaction with 4 steps

1.1: 93 percent / MgSO₄ / CHCl₃ / 20 °C

2.1: TMSOTf / CH₂Cl₂ / 0.25 h / -78 °C

2.2: TBAF / tetrahydrofuran; CH₂Cl₂ / 0.17 h / 0 °C

3.1: HClO₄ / acetonitrile; H₂O / 5 h / 20 °C

With perchloric acid; trimethylsilyl trifluoromethanesulfonate; magnesium sulfate; In dichloromethane; chloroform; water; acetonitrile;
DOI:10.1021/ol0200044

Reference yield:

: 1053616-43-5
(3R,3aR,6aR)-3-tert-butyldiphenylsilyloxymethyl-N-(2',3':5',6'-di-O-isopropylidene-α-L-gulofuranosyl)tetrahydrofuro[2,3-d]isoxazol-5-one

: 420846-38-4
(3R,3aR,6aR)-3-(tert-butyldiphenylsilyloxymethyl)-N-(tert-butyloxycarbonyl)tetrahydrofuro[2,3-d]isoxazol-5-one

Guidance literature:: Multi-step reaction with 2 steps

1: HClO₄ / acetonitrile; H₂O / 5 h / 20 °C

With perchloric acid; In water; acetonitrile;
DOI:10.1021/ol0200044