(4S,5S)-5-[(1S)-2-tert-butyldimethylsilyloxy-1-methylethyl]-2,2-dimethyl-5-[(1R)-1-methyl-2-phenylsulfonylethyl]-1,3-dioxolane

Base Information

Chemical Name:(4S,5S)-5-[(1S)-2-tert-butyldimethylsilyloxy-1-methylethyl]-2,2-dimethyl-5-[(1R)-1-methyl-2-phenylsulfonylethyl]-1,3-dioxolane
CAS No.:489440-28-0
Molecular Formula:C₂₃H₄₀O₅SSi
Molecular Weight:456.719
Hs Code.:

Synonyms:(4S,5S)-5-[(1S)-2-tert-butyldimethylsilyloxy-1-methylethyl]-2,2-dimethyl-5-[(1R)-1-methyl-2-phenylsulfonylethyl]-1,3-dioxolane

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Chemical Property of (4S,5S)-5-[(1S)-2-tert-butyldimethylsilyloxy-1-methylethyl]-2,2-dimethyl-5-[(1R)-1-methyl-2-phenylsulfonylethyl]-1,3-dioxolane

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Technology Process of (4S,5S)-5-[(1S)-2-tert-butyldimethylsilyloxy-1-methylethyl]-2,2-dimethyl-5-[(1R)-1-methyl-2-phenylsulfonylethyl]-1,3-dioxolane

There total 5 articles about (4S,5S)-5-[(1S)-2-tert-butyldimethylsilyloxy-1-methylethyl]-2,2-dimethyl-5-[(1R)-1-methyl-2-phenylsulfonylethyl]-1,3-dioxolane 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: 87.0%

: 873-55-2
sodium benzenesulfonate

: 489440-27-9
(4S,5S)-5-[(1S)-2-tert-butyldimethylsilyloxy-1-methylethyl]-2,2-dimethyl-4-[(1S)-1-methyl-2-(4-methylphenylsulfonyloxy)ethyl]-1,3-dioxolane

: 489440-28-0
(4S,5S)-5-[(1S)-2-tert-butyldimethylsilyloxy-1-methylethyl]-2,2-dimethyl-5-[(1R)-1-methyl-2-phenylsulfonylethyl]-1,3-dioxolane

Guidance literature:: With sodium iodide; In N,N-dimethyl-formamide; at 70 ℃; for 12h;
DOI:10.1002/1099-0690(200208)2002:15<2613::AID-EJOC2613<3.0.CO;2-Y

Reference yield:

: 81706-69-6
(4R,trans)-2,2,α,α,α',α'-hexamethyl-1,3-dioxolane-4,5-dimethanol

: 489440-28-0
(4S,5S)-5-[(1S)-2-tert-butyldimethylsilyloxy-1-methylethyl]-2,2-dimethyl-5-[(1R)-1-methyl-2-phenylsulfonylethyl]-1,3-dioxolane

Guidance literature:: Multi-step reaction with 5 steps

1.1: 98 percent / methanesulfonyl chloride; 4-dimethylaminopyridine; triethylamine / CH₂Cl₂ / 30 h / 20 °C

2.1: borane*DMSO; triethylborane / dimethylsulfoxide; hexane; diethyl ether / 12 h

2.2: 50 percent / H₂O₂; NaOH; water / 4 h / 20 °C

3.1: 73 percent / sodium hydride / tetrahydrofuran / 1 h / 20 °C

4.1: 99 percent / triethylamine; 4-dimethylaminopyridine / CH₂Cl₂ / 12 h

5.1: 87 percent / sodium iodide / dimethylformamide / 12 h / 70 °C

With dmap; triethyl borane; borane*DMSO; sodium hydride; methanesulfonyl chloride; triethylamine; sodium iodide; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide;
DOI:10.1002/1099-0690(200208)2002:15<2613::AID-EJOC2613<3.0.CO;2-Y

Reference yield:

: 110454-08-5
(4S,5S)-2,2-dimethyl-4,5-bis(1-methylvinyl)-1,3-dioxolane

: 489440-28-0
(4S,5S)-5-[(1S)-2-tert-butyldimethylsilyloxy-1-methylethyl]-2,2-dimethyl-5-[(1R)-1-methyl-2-phenylsulfonylethyl]-1,3-dioxolane

Guidance literature:: Multi-step reaction with 4 steps

1.1: borane*DMSO; triethylborane / dimethylsulfoxide; hexane; diethyl ether / 12 h

1.2: 50 percent / H₂O₂; NaOH; water / 4 h / 20 °C

2.1: 73 percent / sodium hydride / tetrahydrofuran / 1 h / 20 °C

3.1: 99 percent / triethylamine; 4-dimethylaminopyridine / CH₂Cl₂ / 12 h

4.1: 87 percent / sodium iodide / dimethylformamide / 12 h / 70 °C

With dmap; triethyl borane; borane*DMSO; sodium hydride; triethylamine; sodium iodide; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide;
DOI:10.1002/1099-0690(200208)2002:15<2613::AID-EJOC2613<3.0.CO;2-Y