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

Base Information

Chemical Name:2-[(E)-(2S,5S)-2-(tert-Butyl-dimethyl-silanyloxy)-5-hydroxy-6-(4-methoxy-benzyloxy)-hex-3-enyl]-malonic acid diethyl ester
CAS No.:477198-57-5
Molecular Formula:C₂₇H₄₄O₈Si
Molecular Weight:524.727
Hs Code.:

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

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

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

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

: 477198-55-3
diethyl (2S)-2-[2-(tert-butyldimethylsilyloxy)-6-(4-methoxyphenylmethoxy)-5-oxo-hex-3-enyl]malonate

: 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

Guidance literature:: With dimethylsulfide borane complex; (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole; In dichloromethane; at -20 ℃; for 13.5h;
DOI:10.1021/ol0267174

Reference yield:

: 69739-34-0
t-butyldimethylsiyl triflate

: 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

Guidance literature:: Multi-step reaction with 5 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

With pyridine; dimethylsulfide borane complex; hydrogen; sodium hydride; palladium on activated charcoal; (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole; In 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

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

Guidance literature:: Multi-step reaction with 2 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

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