dimethyl (2'E,1'R)-2-[1'-acetoxy-4'-(tertbutyldiphenylsilyloxy)-2'-buten-1'-yl]-2-methylmalonate

Base Information

Chemical Name:dimethyl (2'E,1'R)-2-[1'-acetoxy-4'-(tertbutyldiphenylsilyloxy)-2'-buten-1'-yl]-2-methylmalonate
CAS No.:169689-13-8
Molecular Formula:C₂₈H₃₆O₇Si
Molecular Weight:512.675
Hs Code.:

Synonyms:dimethyl (2'E,1'R)-2-[1'-acetoxy-4'-(tertbutyldiphenylsilyloxy)-2'-buten-1'-yl]-2-methylmalonate

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Chemical Property of dimethyl (2'E,1'R)-2-[1'-acetoxy-4'-(tertbutyldiphenylsilyloxy)-2'-buten-1'-yl]-2-methylmalonate

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Technology Process of dimethyl (2'E,1'R)-2-[1'-acetoxy-4'-(tertbutyldiphenylsilyloxy)-2'-buten-1'-yl]-2-methylmalonate

There total 3 articles about dimethyl (2'E,1'R)-2-[1'-acetoxy-4'-(tertbutyldiphenylsilyloxy)-2'-buten-1'-yl]-2-methylmalonate 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: 86.0%

: sodium salt of dimethyl methylmalonate

: 169689-20-7
(E)-1,1-diacetoxy-4-(t-butyldiphenylsilyloxy)-2-butene

: dimethyl (2'E,1'S)-2-[1'-acetoxy-4'-(tertbutyldiphenylsilyloxy)-2'-buten-1'-yl]-2-methylmalonate

: 169689-13-8
dimethyl (2'E,1'R)-2-[1'-acetoxy-4'-(tertbutyldiphenylsilyloxy)-2'-buten-1'-yl]-2-methylmalonate

: 5-(tert-butyl-diphenyl-silanyloxymethyl)-2,6-bis-methoxycarbonyl-2,6-dimethyl-hept-3-enedioic acid dimethyl ester

Guidance literature:: With 1,3-bis-(diphenylphosphino)propane; In tetrahydrofuran;
DOI:10.1021/ja003774o

Reference yield:

: 609-02-9
methyl-malonic acid dimethylester

: 169689-20-7
(E)-1,1-diacetoxy-4-(t-butyldiphenylsilyloxy)-2-butene

: dimethyl (2'E,1'S)-2-[1'-acetoxy-4'-(tertbutyldiphenylsilyloxy)-2'-buten-1'-yl]-2-methylmalonate

: 169689-13-8
dimethyl (2'E,1'R)-2-[1'-acetoxy-4'-(tertbutyldiphenylsilyloxy)-2'-buten-1'-yl]-2-methylmalonate

Guidance literature:: With bis(η3-allyl-μ-chloropalladium(II)); sodium hydride; (1R,2R)-1,2-bis[(2-diphenylphosphanyl)benzoylamino]cyclohexane; Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts; 1.) THF, RT, 2.) THF, 0 deg C, 5 h;
DOI:10.1021/ja00132a026

Reference yield:

: 131380-48-8
(E)-4-(t-butyldiphenylsilyl)oxy-2-butenal

: 169689-13-8
dimethyl (2'E,1'R)-2-[1'-acetoxy-4'-(tertbutyldiphenylsilyloxy)-2'-buten-1'-yl]-2-methylmalonate

Guidance literature:: Multi-step reaction with 2 steps

1: 97 percent / FeCl₃

2: 1.) NaH, 2.) (π-allyl)palladium chloride dimer, bis(2-triphenylphosphinobenzoyl)-(1R,2R)-cyclohexyldiamide / 1.) THF, RT, 2.) THF, 0 deg C, 5 h

With bis(η3-allyl-μ-chloropalladium(II)); iron(III) chloride; sodium hydride; (1R,2R)-1,2-bis[(2-diphenylphosphanyl)benzoylamino]cyclohexane;
DOI:10.1021/ja00132a026