(2S,3R)-methyl 3-(4-((tert-butyldimethylsilyloxy)methyl)phenyl)-2,3-dihydroxypropanoate

Base Information

Chemical Name:(2S,3R)-methyl 3-(4-((tert-butyldimethylsilyloxy)methyl)phenyl)-2,3-dihydroxypropanoate
CAS No.:1353660-32-8
Molecular Formula:C₁₇H₂₈O₅Si
Molecular Weight:340.492
Hs Code.:

Synonyms:(2S,3R)-methyl 3-(4-((tert-butyldimethylsilyloxy)methyl)phenyl)-2,3-dihydroxypropanoate

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (2S,3R)-methyl 3-(4-((tert-butyldimethylsilyloxy)methyl)phenyl)-2,3-dihydroxypropanoate

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Technology Process of (2S,3R)-methyl 3-(4-((tert-butyldimethylsilyloxy)methyl)phenyl)-2,3-dihydroxypropanoate

There total 2 articles about (2S,3R)-methyl 3-(4-((tert-butyldimethylsilyloxy)methyl)phenyl)-2,3-dihydroxypropanoate 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%

: 1353660-31-7
(E)-methyl 4-[tert-butyldimethylsilyloxymethyl]cinnamate

: 1353660-32-8
(2S,3R)-methyl 3-(4-((tert-butyldimethylsilyloxy)methyl)phenyl)-2,3-dihydroxypropanoate

Guidance literature:: With hydroquinidine 1 4-phthalazinediyl diether; potassium dioxotetrahydroxoosmate(VI); methanesulfonamide; water; potassium carbonate; potassium hydrogencarbonate; potassium hexacyanoferrate(III); In tert-butyl alcohol; at 0 - 20 ℃; optical yield given as %ee; stereoselective reaction; Inert atmosphere;
DOI:10.1002/chem.201101978

Reference yield:

: 141286-90-0,117390-06-4
methyl (E)-3-(4-(hydroxymethyl)phenyl)acrylate

: 1353660-32-8
(2S,3R)-methyl 3-(4-((tert-butyldimethylsilyloxy)methyl)phenyl)-2,3-dihydroxypropanoate

Guidance literature:: Multi-step reaction with 2 steps

1: 1H-imidazole / dichloromethane / 1 h / 20 °C / Inert atmosphere; Cooling with water bath

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

With 1H-imidazole; hydroquinidine 1 4-phthalazinediyl diether; potassium dioxotetrahydroxoosmate(VI); methanesulfonamide; water; potassium carbonate; potassium hydrogencarbonate; potassium hexacyanoferrate(III); In dichloromethane; tert-butyl alcohol; 2: Sharpless dihydroxylation;
DOI:10.1002/chem.201101978

Reference yield: 63.0%

: 1353660-32-8
(2S,3R)-methyl 3-(4-((tert-butyldimethylsilyloxy)methyl)phenyl)-2,3-dihydroxypropanoate

: 1353660-40-8
(2S,3S)-methyl 3-azido-3-(4-((tert-butyldimethylsilyloxy)methyl)phenyl)-2-hydroxypropanoate

Guidance literature:: With hydrogen azide; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; toluene; at -25 - 20 ℃; for 23h; regioselective reaction; Inert atmosphere;
DOI:10.1002/chem.201101978