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

Base Information

• Chemical Name: (Z)-2-tert-butyldiphenylsilyloxy-N-(2,3:5,6-di-O-isopropylidene-α-L-gulofuranosyl)ethylideneamine N-oxide
• CAS No.: 1054646-14-8
• Molecular Formula: C₃₀H₄₁NO₇Si
• Molecular Weight: 555.744
• Mol file: 1054646-14-8.mol

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

Chemical Property of (Z)-2-tert-butyldiphenylsilyloxy-N-(2,3:5,6-di-O-isopropylidene-α-L-gulofuranosyl)ethylideneamine N-oxide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (Z)-2-tert-butyldiphenylsilyloxy-N-(2,3:5,6-di-O-isopropylidene-α-L-gulofuranosyl)ethylideneamine N-oxide

There total 1 articles about (Z)-2-tert-butyldiphenylsilyloxy-N-(2,3:5,6-di-O-isopropylidene-α-L-gulofuranosyl)ethylideneamine N-oxide 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: 93.0%

2,3:5,6-O-diisopropylidene-L-gulose oxime (420846-29-3) + (tert-butyldiphenylsilanyloxy)acetaldehyde (115869-43-7) → (Z)-2-tert-butyldiphenylsilyloxy-N-(2,3:5,6-di-O-isopropylidene-α-L-gulofuranosyl)ethylideneamine N-oxide (1054646-14-8)

Guidance literature:

With magnesium sulfate; In chloroform; at 20 ℃;

DOI:10.1021/ol0200044

Reference yield:

(furan-2-yloxy)-trimethylsilane (61550-02-5) + (Z)-2-tert-butyldiphenylsilyloxy-N-(2,3:5,6-di-O-isopropylidene-α-L-gulofuranosyl)ethylideneamine N-oxide (1054646-14-8) → (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 + (3R,3aR,6aR)-3-tert-butyldiphenylsilyloxymethyl-N-(2',3':5',6'-di-O-isopropylidene-α-L-gulofuranosyl)tetrahydrofuro[2,3-d]isoxazol-5-one (1053616-43-5)

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:

(furan-2-yloxy)-trimethylsilane (61550-02-5) + (Z)-2-tert-butyldiphenylsilyloxy-N-(2,3:5,6-di-O-isopropylidene-α-L-gulofuranosyl)ethylideneamine N-oxide (1054646-14-8) → (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 + (3R,3aR,6aR)-3-tert-butyldiphenylsilyloxymethyl-N-(2',3':5',6'-di-O-isopropylidene-α-L-gulofuranosyl)tetrahydrofuro[2,3-d]isoxazol-5-one (1053616-43-5)

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

upstream raw materials:

2,3:5,6-O-diisopropylidene-L-gulose oxime

(tert-butyldiphenylsilanyloxy)acetaldehyde

Downstream raw materials:

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