(4aR,6R,7R,8aR)-8-((tert-butyldimethylsilyl)oxy)-2-phenyl-6-(2,2,2-trichloro-1-iminoethoxy)hexahydropyrano[3,2-d][1,3]dioxin-7-yl benzoate

Base Information

Chemical Name:(4aR,6R,7R,8aR)-8-((tert-butyldimethylsilyl)oxy)-2-phenyl-6-(2,2,2-trichloro-1-iminoethoxy)hexahydropyrano[3,2-d][1,3]dioxin-7-yl benzoate
CAS No.:649554-90-5
Molecular Formula:C₂₈H₃₄Cl₃NO₇Si
Molecular Weight:631.025
Hs Code.:

Synonyms:(4aR,6R,7R,8aR)-8-((tert-butyldimethylsilyl)oxy)-2-phenyl-6-(2,2,2-trichloro-1-iminoethoxy)hexahydropyrano[3,2-d][1,3]dioxin-7-yl benzoate

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Chemical Property of (4aR,6R,7R,8aR)-8-((tert-butyldimethylsilyl)oxy)-2-phenyl-6-(2,2,2-trichloro-1-iminoethoxy)hexahydropyrano[3,2-d][1,3]dioxin-7-yl benzoate

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Technology Process of (4aR,6R,7R,8aR)-8-((tert-butyldimethylsilyl)oxy)-2-phenyl-6-(2,2,2-trichloro-1-iminoethoxy)hexahydropyrano[3,2-d][1,3]dioxin-7-yl benzoate

There total 3 articles about (4aR,6R,7R,8aR)-8-((tert-butyldimethylsilyl)oxy)-2-phenyl-6-(2,2,2-trichloro-1-iminoethoxy)hexahydropyrano[3,2-d][1,3]dioxin-7-yl benzoate 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: 95.0%

: 545-06-2
trichloroacetonitrile

: 2-O-benzoyl-4,6-O-benzylidene-3-O-(tert-butyldimethylsilyl)-D-glucopyranose

: 649554-90-5
(4aR,6R,7R,8aR)-8-((tert-butyldimethylsilyl)oxy)-2-phenyl-6-(2,2,2-trichloro-1-iminoethoxy)hexahydropyrano[3,2-d][1,3]dioxin-7-yl benzoate

Guidance literature:: With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 0 ℃; for 4h;
DOI:10.1016/j.tetlet.2003.09.230

Reference yield:

: 545-06-2
trichloroacetonitrile

: 2-O-benzoyl-4,6-O-benzylidene-3-O-(tert-butyldimethylsilyl)-D-glucopyranose

: (2R,4aR,6S,7R,8S,8aR)-8-((tert-butyldimethylsilyl)oxy)-2-phenyl-6-(2,2,2-trichloro-1-iminoethoxy)hexahydropyrano[3,2-d][1,3]dioxin-7-yl benzoate

: 649554-90-5
(4aR,6R,7R,8aR)-8-((tert-butyldimethylsilyl)oxy)-2-phenyl-6-(2,2,2-trichloro-1-iminoethoxy)hexahydropyrano[3,2-d][1,3]dioxin-7-yl benzoate

Guidance literature:: With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 20 ℃; for 5h; optical yield given as %de;
DOI:10.1016/j.carres.2008.12.014

Reference yield:

: 460741-88-2
ethyl 2-O-benzoyl-4,6-O-benzylidene-3-O-(tert-butyldimethylsilyl)-1-thio-β-D-glucopyranoside

: 649554-90-5
(4aR,6R,7R,8aR)-8-((tert-butyldimethylsilyl)oxy)-2-phenyl-6-(2,2,2-trichloro-1-iminoethoxy)hexahydropyrano[3,2-d][1,3]dioxin-7-yl benzoate

Guidance literature:: Multi-step reaction with 3 steps

1: 90 percent / N-bromosuccinimide; TMSOTf / CH₂Cl₂; H₂O / 0.17 h / 0 °C

2: 95 percent / Et₃N / CH₂Cl₂ / 24 h / 20 °C

3: 95 percent / DBU / CH₂Cl₂ / 4 h / 0 °C

With N-Bromosuccinimide; trimethylsilyl trifluoromethanesulfonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In dichloromethane; water;
DOI:10.1016/j.tetlet.2003.09.230