diethyl (2S,3S)-3-(tert-butyldimethylsilyloxy)-2-[3-(4-methoxyphenylmethoxy)-propenyl]-cyclobutane-1,1-dicarboxylate

Base Information

Chemical Name:diethyl (2S,3S)-3-(tert-butyldimethylsilyloxy)-2-[3-(4-methoxyphenylmethoxy)-propenyl]-cyclobutane-1,1-dicarboxylate
CAS No.:477198-59-7
Molecular Formula:C₂₇H₄₂O₇Si
Molecular Weight:506.712
Hs Code.:

Synonyms:diethyl (2S,3S)-3-(tert-butyldimethylsilyloxy)-2-[3-(4-methoxyphenylmethoxy)-propenyl]-cyclobutane-1,1-dicarboxylate

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Chemical Property of diethyl (2S,3S)-3-(tert-butyldimethylsilyloxy)-2-[3-(4-methoxyphenylmethoxy)-propenyl]-cyclobutane-1,1-dicarboxylate

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Technology Process of diethyl (2S,3S)-3-(tert-butyldimethylsilyloxy)-2-[3-(4-methoxyphenylmethoxy)-propenyl]-cyclobutane-1,1-dicarboxylate

There total 8 articles about diethyl (2S,3S)-3-(tert-butyldimethylsilyloxy)-2-[3-(4-methoxyphenylmethoxy)-propenyl]-cyclobutane-1,1-dicarboxylate 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: 75.0%

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

: 477198-59-7
diethyl (2S,3S)-3-(tert-butyldimethylsilyloxy)-2-[3-(4-methoxyphenylmethoxy)-propenyl]-cyclobutane-1,1-dicarboxylate

Guidance literature:: With sodium hydride; In toluene; at 120 ℃; for 0.5h;
DOI:10.1021/ol0267174

Reference yield:

: 69739-34-0
t-butyldimethylsiyl triflate

: 477198-59-7
diethyl (2S,3S)-3-(tert-butyldimethylsilyloxy)-2-[3-(4-methoxyphenylmethoxy)-propenyl]-cyclobutane-1,1-dicarboxylate

Guidance literature:: Multi-step reaction with 7 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

7: 75 percent / NaH / toluene / 0.5 h / 120 °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; toluene;
DOI:10.1021/ol0267174

Reference yield:

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

: 477198-59-7
diethyl (2S,3S)-3-(tert-butyldimethylsilyloxy)-2-[3-(4-methoxyphenylmethoxy)-propenyl]-cyclobutane-1,1-dicarboxylate

Guidance literature:: Multi-step reaction with 4 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

4: 75 percent / NaH / toluene / 0.5 h / 120 °C

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