(2S,3S)-{3-(tert-butyldimethylsilyloxy)-1-hydroxymethyl-2-[3-(4-methoxyphenylmethoxy)-propenyl]-cyclobutyl}-methanol

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Chemical Name:(2S,3S)-{3-(tert-butyldimethylsilyloxy)-1-hydroxymethyl-2-[3-(4-methoxyphenylmethoxy)-propenyl]-cyclobutyl}-methanol
CAS No.:477198-64-4
Molecular Formula:C₂₃H₃₈O₅Si
Molecular Weight:422.637
Hs Code.:

Synonyms:(2S,3S)-{3-(tert-butyldimethylsilyloxy)-1-hydroxymethyl-2-[3-(4-methoxyphenylmethoxy)-propenyl]-cyclobutyl}-methanol

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Chemical Property of (2S,3S)-{3-(tert-butyldimethylsilyloxy)-1-hydroxymethyl-2-[3-(4-methoxyphenylmethoxy)-propenyl]-cyclobutyl}-methanol

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Technology Process of (2S,3S)-{3-(tert-butyldimethylsilyloxy)-1-hydroxymethyl-2-[3-(4-methoxyphenylmethoxy)-propenyl]-cyclobutyl}-methanol

There total 9 articles about (2S,3S)-{3-(tert-butyldimethylsilyloxy)-1-hydroxymethyl-2-[3-(4-methoxyphenylmethoxy)-propenyl]-cyclobutyl}-methanol 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: 92.0%

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

: 477198-64-4
(2S,3S)-{3-(tert-butyldimethylsilyloxy)-1-hydroxymethyl-2-[3-(4-methoxyphenylmethoxy)-propenyl]-cyclobutyl}-methanol

Guidance literature:: With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 - 20 ℃;
DOI:10.1021/ol0267174

Reference yield:

: 69739-34-0
t-butyldimethylsiyl triflate

: 477198-64-4
(2S,3S)-{3-(tert-butyldimethylsilyloxy)-1-hydroxymethyl-2-[3-(4-methoxyphenylmethoxy)-propenyl]-cyclobutyl}-methanol

Guidance literature:: Multi-step reaction with 8 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

8: 92 percent / lithium aluminum hydride / tetrahydrofuran / 0 - 20 °C

With pyridine; lithium aluminium tetrahydride; 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

: 477198-64-4
(2S,3S)-{3-(tert-butyldimethylsilyloxy)-1-hydroxymethyl-2-[3-(4-methoxyphenylmethoxy)-propenyl]-cyclobutyl}-methanol

Guidance literature:: Multi-step reaction with 5 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

5: 92 percent / lithium aluminum hydride / tetrahydrofuran / 0 - 20 °C

With pyridine; lithium aluminium tetrahydride; 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