diethyl (2S,5S)-2-[2-(tert-butyldimethylsilyloxy)-5-(2,6-dimethylphenoxycarbonyloxy)-6-(4-methoxyphenylmethoxy)-hex-3-enyl]malonate

Base Information

Chemical Name:diethyl (2S,5S)-2-[2-(tert-butyldimethylsilyloxy)-5-(2,6-dimethylphenoxycarbonyloxy)-6-(4-methoxyphenylmethoxy)-hex-3-enyl]malonate
CAS No.:477198-51-9
Molecular Formula:C₃₆H₅₂O₁₀Si
Molecular Weight:672.888
Hs Code.:

Synonyms:diethyl (2S,5S)-2-[2-(tert-butyldimethylsilyloxy)-5-(2,6-dimethylphenoxycarbonyloxy)-6-(4-methoxyphenylmethoxy)-hex-3-enyl]malonate

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Chemical Property of diethyl (2S,5S)-2-[2-(tert-butyldimethylsilyloxy)-5-(2,6-dimethylphenoxycarbonyloxy)-6-(4-methoxyphenylmethoxy)-hex-3-enyl]malonate

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Technology Process of diethyl (2S,5S)-2-[2-(tert-butyldimethylsilyloxy)-5-(2,6-dimethylphenoxycarbonyloxy)-6-(4-methoxyphenylmethoxy)-hex-3-enyl]malonate

There total 7 articles about diethyl (2S,5S)-2-[2-(tert-butyldimethylsilyloxy)-5-(2,6-dimethylphenoxycarbonyloxy)-6-(4-methoxyphenylmethoxy)-hex-3-enyl]malonate 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:

: 876-99-3
2,6-dimethylphenyl chloroformic acid ester

: 477198-57-5
2-[(E)-(2S,5S)-2-(tert-Butyl-dimethyl-silanyloxy)-5-hydroxy-6-(4-methoxy-benzyloxy)-hex-3-enyl]-malonic acid diethyl ester

: 477198-51-9
diethyl (2S,5S)-2-[2-(tert-butyldimethylsilyloxy)-5-(2,6-dimethylphenoxycarbonyloxy)-6-(4-methoxyphenylmethoxy)-hex-3-enyl]malonate

Guidance literature:: With pyridine; dmap; In tetrahydrofuran; at 20 ℃; for 2h;
DOI:10.1021/ol0267174

Reference yield:

: 69739-34-0
t-butyldimethylsiyl triflate

: 477198-51-9
diethyl (2S,5S)-2-[2-(tert-butyldimethylsilyloxy)-5-(2,6-dimethylphenoxycarbonyloxy)-6-(4-methoxyphenylmethoxy)-hex-3-enyl]malonate

Guidance literature:: Multi-step reaction with 6 steps

1: 19.76 g / pyridine / 2 h / 0 °C

2: 93 percent / NaH / dimethylformamide / 40 h / Heating

3: 95 percent / H₂ / Pd/C / ethyl acetate / 48 h / 2585.81 Torr

4: 90 percent / CHCl₃ / 7 h / Heating

5: BH₃*S(CH₃)2 / (S)-2-Me-4,4-Ph₂-1-aza-2-bora-3-oxabicyclo[3.3.0]octan / CH₂Cl₂ / 13.5 h / -20 °C

6: 14.53 g / pyridine / DMAP / tetrahydrofuran / 2 h / 20 °C

With pyridine; dimethylsulfide borane complex; hydrogen; sodium hydride; dmap; palladium on activated charcoal; (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole; In tetrahydrofuran; dichloromethane; chloroform; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1021/ol0267174

Reference yield:

: 173613-40-6
1-(4-methoxyphenylmethoxy)-3-(triphenylphosphanylidene)-propan-2-one

: 477198-51-9
diethyl (2S,5S)-2-[2-(tert-butyldimethylsilyloxy)-5-(2,6-dimethylphenoxycarbonyloxy)-6-(4-methoxyphenylmethoxy)-hex-3-enyl]malonate

Guidance literature:: Multi-step reaction with 3 steps

1: 90 percent / CHCl₃ / 7 h / Heating

2: BH₃*S(CH₃)2 / (S)-2-Me-4,4-Ph₂-1-aza-2-bora-3-oxabicyclo[3.3.0]octan / CH₂Cl₂ / 13.5 h / -20 °C

3: 14.53 g / pyridine / DMAP / tetrahydrofuran / 2 h / 20 °C

With pyridine; dimethylsulfide borane complex; dmap; (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole; In tetrahydrofuran; dichloromethane; chloroform;
DOI:10.1021/ol0267174