(2S,3S,4R)-5-(4-Methoxy-benzyloxy)-2,4-dimethyl-3-triisopropylsilanyloxy-pentanoic acid tert-butyl ester

Base Information

Chemical Name:(2S,3S,4R)-5-(4-Methoxy-benzyloxy)-2,4-dimethyl-3-triisopropylsilanyloxy-pentanoic acid tert-butyl ester
CAS No.:850416-18-1
Molecular Formula:C₂₈H₅₀O₅Si
Molecular Weight:494.788
Hs Code.:

Synonyms:(2S,3S,4R)-5-(4-Methoxy-benzyloxy)-2,4-dimethyl-3-triisopropylsilanyloxy-pentanoic acid tert-butyl ester

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Chemical Property of (2S,3S,4R)-5-(4-Methoxy-benzyloxy)-2,4-dimethyl-3-triisopropylsilanyloxy-pentanoic acid tert-butyl ester

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Technology Process of (2S,3S,4R)-5-(4-Methoxy-benzyloxy)-2,4-dimethyl-3-triisopropylsilanyloxy-pentanoic acid tert-butyl ester

There total 5 articles about (2S,3S,4R)-5-(4-Methoxy-benzyloxy)-2,4-dimethyl-3-triisopropylsilanyloxy-pentanoic acid tert-butyl 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: 92.0%

: 80522-42-5
triisopropylsilyl trifluoromethanesulfonate

: 3-hydroxy-5-(4-methoxy-benzyloxy)-2,4-dimethyl-pentanoic acid tert-butyl ester

: 850416-18-1
(2S,3S,4R)-5-(4-Methoxy-benzyloxy)-2,4-dimethyl-3-triisopropylsilanyloxy-pentanoic acid tert-butyl ester

Guidance literature:: With 2,6-dimethylpyridine; In dichloromethane; at -15 ℃; for 2.5h;
DOI:10.1055/s-2005-862351

Reference yield:

: 89238-99-3
O-(4-methoxybenzyl)-trichloroacetimidate

: 850416-18-1
(2S,3S,4R)-5-(4-Methoxy-benzyloxy)-2,4-dimethyl-3-triisopropylsilanyloxy-pentanoic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 5 steps

1.1: 75 percent / CSA / CH₂Cl₂ / 24 h / 20 °C

2.1: LDA / tetrahydrofuran / -40 °C

2.2: 85 percent / tetrahydrofuran / 3 h / -40 °C

3.1: 74 percent / H₂ / {Ru[(S)-SYNPHOS]Br₂} / methanol; 2-methyl-propan-2-ol / 23 h / 50 °C / 56254.5 Torr

4.1: LDA / tetrahydrofuran / -40 °C

4.2: 72 percent / tetrahydrofuran; hexamethylphosphoric acid triamide / 6 h / -40 - -10 °C

5.1: 92 percent / 2.6-lutidine / CH₂Cl₂ / 2.5 h / -15 °C

With 2,6-dimethylpyridine; camphor-10-sulfonic acid; hydrogen; lithium diisopropyl amide; RuBr₂[(S)-(C₆H₂OCH₂CH₂OP(C₆H₅)2)2]; In tetrahydrofuran; methanol; dichloromethane; tert-butyl alcohol;
DOI:10.1055/s-2005-862351

Reference yield:

: 212051-35-9
(R)-methyl 3-((4-methoxybenzyl)oxy)-2-methylpropanoate

: 850416-18-1
(2S,3S,4R)-5-(4-Methoxy-benzyloxy)-2,4-dimethyl-3-triisopropylsilanyloxy-pentanoic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: LDA / tetrahydrofuran / -40 °C

1.2: 85 percent / tetrahydrofuran / 3 h / -40 °C

2.1: 74 percent / H₂ / {Ru[(S)-SYNPHOS]Br₂} / methanol; 2-methyl-propan-2-ol / 23 h / 50 °C / 56254.5 Torr

3.1: LDA / tetrahydrofuran / -40 °C

3.2: 72 percent / tetrahydrofuran; hexamethylphosphoric acid triamide / 6 h / -40 - -10 °C

4.1: 92 percent / 2.6-lutidine / CH₂Cl₂ / 2.5 h / -15 °C

With 2,6-dimethylpyridine; hydrogen; lithium diisopropyl amide; RuBr₂[(S)-(C₆H₂OCH₂CH₂OP(C₆H₅)2)2]; In tetrahydrofuran; methanol; dichloromethane; tert-butyl alcohol;
DOI:10.1055/s-2005-862351