(2R,3S)-2-(2-(benzyloxy)ethyl)-6-((3S,4R)-4-tert-butyldimethylsilyloxy-5-(4-methoxybenzyloxy)-3-methylpentyl)-3-methyl-3,4-dihydro-2H-pyran

Base Information

Chemical Name:(2R,3S)-2-(2-(benzyloxy)ethyl)-6-((3S,4R)-4-tert-butyldimethylsilyloxy-5-(4-methoxybenzyloxy)-3-methylpentyl)-3-methyl-3,4-dihydro-2H-pyran
CAS No.:1299293-80-3
Molecular Formula:C₃₅H₅₄O₅Si
Molecular Weight:582.896
Hs Code.:

Synonyms:(2R,3S)-2-(2-(benzyloxy)ethyl)-6-((3S,4R)-4-tert-butyldimethylsilyloxy-5-(4-methoxybenzyloxy)-3-methylpentyl)-3-methyl-3,4-dihydro-2H-pyran

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Chemical Property of (2R,3S)-2-(2-(benzyloxy)ethyl)-6-((3S,4R)-4-tert-butyldimethylsilyloxy-5-(4-methoxybenzyloxy)-3-methylpentyl)-3-methyl-3,4-dihydro-2H-pyran

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Technology Process of (2R,3S)-2-(2-(benzyloxy)ethyl)-6-((3S,4R)-4-tert-butyldimethylsilyloxy-5-(4-methoxybenzyloxy)-3-methylpentyl)-3-methyl-3,4-dihydro-2H-pyran

There total 11 articles about (2R,3S)-2-(2-(benzyloxy)ethyl)-6-((3S,4R)-4-tert-butyldimethylsilyloxy-5-(4-methoxybenzyloxy)-3-methylpentyl)-3-methyl-3,4-dihydro-2H-pyran 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: 83.0%

: 1299293-79-0
(1R,2S)-1-[2-(benzyloxy)ethyl]-2-methylpent-4-en-1-yl (4S,5R)-5-{[tert-butyl(dimethyl)-silyl]oxy}-6-[(4-methoxybenzyl)oxy]-4-methylhexanoate

: 1299293-80-3
(2R,3S)-2-(2-(benzyloxy)ethyl)-6-((3S,4R)-4-tert-butyldimethylsilyloxy-5-(4-methoxybenzyloxy)-3-methylpentyl)-3-methyl-3,4-dihydro-2H-pyran

Guidance literature:: With 1,1-Dibromoethane; N,N,N,N,-tetramethylethylenediamine; titanium tetrachloride; lead(II) chloride; zinc; In tetrahydrofuran; dichloromethane; at 55 ℃; for 2.5h;
DOI:10.1055/s-0030-1259287

Reference yield:

: 1299293-74-5
ethyl (4S,5R)-5-{[tert-butyl(dimethyl)silyl]oxy}-6-[(4-methoxybenzyl)oxy]-4-methylhexanoate

: 1299293-80-3
(2R,3S)-2-(2-(benzyloxy)ethyl)-6-((3S,4R)-4-tert-butyldimethylsilyloxy-5-(4-methoxybenzyloxy)-3-methylpentyl)-3-methyl-3,4-dihydro-2H-pyran

Guidance literature:: Multi-step reaction with 3 steps

1.1: water; sodium hydroxide / ethanol / 0 - 20 °C

2.1: 2,4,6-trichlorobenzoyl chloride; triethylamine / toluene / 0.5 h / 20 °C

2.2: 2 h

3.1: 1,1-Dibromoethane; N,N,N,N,-tetramethylethylenediamine; titanium tetrachloride; lead(II) chloride; zinc / tetrahydrofuran; dichloromethane / 2.5 h / 55 °C

With 1,1-Dibromoethane; N,N,N,N,-tetramethylethylenediamine; 2,4,6-trichlorobenzoyl chloride; water; titanium tetrachloride; triethylamine; sodium hydroxide; lead(II) chloride; zinc; In tetrahydrofuran; ethanol; dichloromethane; toluene;
DOI:10.1055/s-0030-1259287

Reference yield:

: 1299293-72-3
(4R)-4-benzyl-3-{(2R,3R)-3-{[tert-butyl(dimethyl)silyl]oxy}-4-[(4-methoxybenzyl)oxy]-2-methylbutanoyl}-1,3-oxazolidin-2-one

: 1299293-80-3
(2R,3S)-2-(2-(benzyloxy)ethyl)-6-((3S,4R)-4-tert-butyldimethylsilyloxy-5-(4-methoxybenzyloxy)-3-methylpentyl)-3-methyl-3,4-dihydro-2H-pyran

Guidance literature:: Multi-step reaction with 7 steps

1.1: lithium borohydride / tetrahydrofuran; methanol / 19 h / 0 - 20 °C

2.1: Dess-Martin periodane / dichloromethane / 3 h / 0 - 20 °C

3.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium chloride / acetonitrile / 1 h / 0 °C

3.2: 0 - 20 °C

4.1: 10% palladium on activated charcoal; hydrogen / ethyl acetate / 18 h / 20 °C

5.1: water; sodium hydroxide / ethanol / 0 - 20 °C

6.1: 2,4,6-trichlorobenzoyl chloride; triethylamine / toluene / 0.5 h / 20 °C

6.2: 2 h

7.1: 1,1-Dibromoethane; N,N,N,N,-tetramethylethylenediamine; titanium tetrachloride; lead(II) chloride; zinc / tetrahydrofuran; dichloromethane / 2.5 h / 55 °C

With lithium borohydride; 1,1-Dibromoethane; N,N,N,N,-tetramethylethylenediamine; 2,4,6-trichlorobenzoyl chloride; 10% palladium on activated charcoal; water; hydrogen; titanium tetrachloride; Dess-Martin periodane; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; lithium chloride; sodium hydroxide; lead(II) chloride; zinc; In tetrahydrofuran; methanol; ethanol; dichloromethane; ethyl acetate; toluene; acetonitrile; 2.1: Dess-Martin oxidation / 3.1: Wittig-Horner reaction / 3.2: Wittig-Horner reaction;
DOI:10.1055/s-0030-1259287