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

Base Information

Chemical Name:(3R,3aR,6aR)-3-tert-butyldiphenylsilyloxymethyl-N-(2',3':5',6'-di-O-isopropylidene-α-L-gulofuranosyl)tetrahydrofuro[2,3-d]isoxazol-5-one
CAS No.:1053616-43-5
Molecular Formula:C₃₄H₄₅NO₉Si
Molecular Weight:639.818
Hs Code.:

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

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

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

There total 5 articles about (3R,3aR,6aR)-3-tert-butyldiphenylsilyloxymethyl-N-(2',3':5',6'-di-O-isopropylidene-α-L-gulofuranosyl)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:

: 61550-02-5
(furan-2-yloxy)-trimethylsilane

: 1054646-14-8
(Z)-2-tert-butyldiphenylsilyloxy-N-(2,3:5,6-di-O-isopropylidene-α-L-gulofuranosyl)ethylideneamine N-oxide

: (3aS,6aS)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-2-[(3aS,4S,6R,6aS)-6-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-tetrahydro-furo[2,3-d]isoxazol-5-one

: 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

Guidance literature:: (furan-2-yloxy)-trimethylsilane; (Z)-2-tert-butyldiphenylsilyloxy-N-(2,3:5,6-di-O-isopropylidene-α-L-gulofuranosyl)ethylideneamine N-oxide; With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -78 ℃; for 0.25h;

With tetrabutyl ammonium fluoride; In tetrahydrofuran; dichloromethane; at 0 ℃; for 0.166667h; Further stages.;
DOI:10.1021/ol0200044

Reference yield:

: 61550-02-5
(furan-2-yloxy)-trimethylsilane

: 1054646-14-8
(Z)-2-tert-butyldiphenylsilyloxy-N-(2,3:5,6-di-O-isopropylidene-α-L-gulofuranosyl)ethylideneamine N-oxide

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

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

: 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

Guidance literature:: (furan-2-yloxy)-trimethylsilane; (Z)-2-tert-butyldiphenylsilyloxy-N-(2,3:5,6-di-O-isopropylidene-α-L-gulofuranosyl)ethylideneamine N-oxide; With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -78 ℃; for 0.25h;

With tetrabutyl ammonium fluoride; In tetrahydrofuran; dichloromethane; at 0 ℃; for 0.166667h; stereoselective reaction;
DOI:10.1039/c1ob06067h

Reference yield:

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

: 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

Guidance literature:: Multi-step reaction with 2 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

With trimethylsilyl trifluoromethanesulfonate; magnesium sulfate; In dichloromethane; chloroform;
DOI:10.1021/ol0200044