(2S,3S)-methyl 3-azido-3-(4-(2-(tert-butyldimethylsilyloxy)ethyl)phenyl)-2-hydroxypropanoate

Base Information

Chemical Name:(2S,3S)-methyl 3-azido-3-(4-(2-(tert-butyldimethylsilyloxy)ethyl)phenyl)-2-hydroxypropanoate
CAS No.:1353660-41-9
Molecular Formula:C₁₈H₂₉N₃O₄Si
Molecular Weight:379.531
Hs Code.:

Synonyms:(2S,3S)-methyl 3-azido-3-(4-(2-(tert-butyldimethylsilyloxy)ethyl)phenyl)-2-hydroxypropanoate

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Chemical Property of (2S,3S)-methyl 3-azido-3-(4-(2-(tert-butyldimethylsilyloxy)ethyl)phenyl)-2-hydroxypropanoate

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Technology Process of (2S,3S)-methyl 3-azido-3-(4-(2-(tert-butyldimethylsilyloxy)ethyl)phenyl)-2-hydroxypropanoate

There total 7 articles about (2S,3S)-methyl 3-azido-3-(4-(2-(tert-butyldimethylsilyloxy)ethyl)phenyl)-2-hydroxypropanoate 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: 80.0%

: 1353660-33-9
(2S,3R)-methyl 3-(4-(2-(tert-butyldimethylsilyloxy)ethyl)phenyl)-2,3-dihydroxypropanoate

: 1353660-41-9
(2S,3S)-methyl 3-azido-3-(4-(2-(tert-butyldimethylsilyloxy)ethyl)phenyl)-2-hydroxypropanoate

Guidance literature:: With hydrogen azide; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; toluene; at -25 - 20 ℃; regioselective reaction; Inert atmosphere;
DOI:10.1002/chem.201101978

Reference yield:

: 167264-41-7
4-[2-(t-butyldimethylsilyloxy)ethyl]benzaldehyde

: 1353660-41-9
(2S,3S)-methyl 3-azido-3-(4-(2-(tert-butyldimethylsilyloxy)ethyl)phenyl)-2-hydroxypropanoate

Guidance literature:: Multi-step reaction with 3 steps

1: dichloromethane / 20 °C / Inert atmosphere

2: hydroquinidine 1 4-phthalazinediyl diether; potassium dioxotetrahydroxoosmate(VI); methanesulfonamide; water; potassium carbonate; potassium hexacyanoferrate(III) / tert-butyl alcohol / 0 - 20 °C / Inert atmosphere

3: hydrogen azide; triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran; toluene / -25 - 20 °C / Inert atmosphere

With hydroquinidine 1 4-phthalazinediyl diether; hydrogen azide; potassium dioxotetrahydroxoosmate(VI); methanesulfonamide; water; potassium carbonate; triphenylphosphine; potassium hexacyanoferrate(III); diethylazodicarboxylate; In tetrahydrofuran; dichloromethane; toluene; tert-butyl alcohol; 1: Wittig reaction / 2: Sharpless dihydroxylation / 3: Mitsunobu reaction;
DOI:10.1002/chem.201101978

Reference yield:

: 167264-35-9
(E)-methyl 3-(4-(2-(tert-butyldimethylsilyloxy)ethyl)phenyl)acrylate

: 1353660-41-9
(2S,3S)-methyl 3-azido-3-(4-(2-(tert-butyldimethylsilyloxy)ethyl)phenyl)-2-hydroxypropanoate

Guidance literature:: Multi-step reaction with 2 steps

1: hydroquinidine 1 4-phthalazinediyl diether; potassium dioxotetrahydroxoosmate(VI); methanesulfonamide; water; potassium carbonate; potassium hexacyanoferrate(III) / tert-butyl alcohol / 0 - 20 °C / Inert atmosphere

2: hydrogen azide; triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran; toluene / -25 - 20 °C / Inert atmosphere

With hydroquinidine 1 4-phthalazinediyl diether; hydrogen azide; potassium dioxotetrahydroxoosmate(VI); methanesulfonamide; water; potassium carbonate; triphenylphosphine; potassium hexacyanoferrate(III); diethylazodicarboxylate; In tetrahydrofuran; toluene; tert-butyl alcohol; 1: Sharpless dihydroxylation / 2: Mitsunobu reaction;
DOI:10.1002/chem.201101978