1-[5,6-di-O-(tert-butyldimethylsilyl)-2,3-dideoxy-β-D-erythro-hex-2-enopyranosyl]-4-(trifluoromethyl)benzene

Base Information

Chemical Name:1-[5,6-di-O-(tert-butyldimethylsilyl)-2,3-dideoxy-β-D-erythro-hex-2-enopyranosyl]-4-(trifluoromethyl)benzene
CAS No.:326474-04-8
Molecular Formula:C₂₅H₄₁F₃O₃Si₂
Molecular Weight:502.765
Hs Code.:

Synonyms:1-[5,6-di-O-(tert-butyldimethylsilyl)-2,3-dideoxy-β-D-erythro-hex-2-enopyranosyl]-4-(trifluoromethyl)benzene

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Chemical Property of 1-[5,6-di-O-(tert-butyldimethylsilyl)-2,3-dideoxy-β-D-erythro-hex-2-enopyranosyl]-4-(trifluoromethyl)benzene

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Technology Process of 1-[5,6-di-O-(tert-butyldimethylsilyl)-2,3-dideoxy-β-D-erythro-hex-2-enopyranosyl]-4-(trifluoromethyl)benzene

There total 1 articles about 1-[5,6-di-O-(tert-butyldimethylsilyl)-2,3-dideoxy-β-D-erythro-hex-2-enopyranosyl]-4-(trifluoromethyl)benzene 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: 48.0%

: 402-43-7
p-trifluoromethylphenyl bromide

: 201232-73-7
p-tert-butylphenyl 4,6-di-O-tert-butyl(dimethyl)silyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside

: 326474-04-8
1-[5,6-di-O-(tert-butyldimethylsilyl)-2,3-dideoxy-β-D-erythro-hex-2-enopyranosyl]-4-(trifluoromethyl)benzene

Guidance literature:: p-trifluoromethylphenyl bromide; With magnesium; In tetrahydrofuran;

p-tert-butylphenyl 4,6-di-O-tert-butyl(dimethyl)silyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside; 1,2-bis(diphenylphosphino)ethane nickel(II) chloride; In tetrahydrofuran; for 24h; Further stages.;
DOI:10.1002/1099-0690(200101)2001:2<375::AID-EJOC375>3.0.CO;2-J

Reference yield: 100.0%

: 326474-04-8
1-[5,6-di-O-(tert-butyldimethylsilyl)-2,3-dideoxy-β-D-erythro-hex-2-enopyranosyl]-4-(trifluoromethyl)benzene

: (2R,3S,6R)-2-Hydroxymethyl-6-(4-trifluoromethyl-phenyl)-3,6-dihydro-2H-pyran-3-ol

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 2h;
DOI:10.1002/1099-0690(200101)2001:2<375::AID-EJOC375>3.0.CO;2-J

Reference yield:

: 326474-04-8
1-[5,6-di-O-(tert-butyldimethylsilyl)-2,3-dideoxy-β-D-erythro-hex-2-enopyranosyl]-4-(trifluoromethyl)benzene

: 1-{4',6'-di-O-[4''-(4-hexyloxybenzoyloxy)benzoyl]-2',3'-dideoxy-β-D-erythro-hexopyranosyl}-4-trifluoromethylbenzene

Guidance literature:: Multi-step reaction with 3 steps

1: 100 percent / Bu₄NF*3H₂O / tetrahydrofuran / 2 h / 20 °C

2: 53 percent / H₂ / [Rh(COD)(dppb)]ClO₄ / ethanol / 24 h / 20 °C / 760.05 Torr

3: 55 percent / N,N'-dicyclohexylcarbodiimide; DMAP / CH₂Cl₂ / 25 °C

With dmap; tetrabutyl ammonium fluoride; hydrogen; dicyclohexyl-carbodiimide; [Rh(COD)(1,4-bis(diphenylphosphino)butane)]ClO₄; In tetrahydrofuran; ethanol; dichloromethane;
DOI:10.1002/1099-0690(200101)2001:2<375::AID-EJOC375>3.0.CO;2-J