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

Base Information

Chemical Name:1-[4,6-di-O-(tert-butyldimethylsilyl)-2,3-dideoxy-β-D-erythro-hex-2-enopyranosyl]-4-methylbenzene
CAS No.:201232-91-9
Molecular Formula:C₂₅H₄₄O₃Si₂
Molecular Weight:448.794
Hs Code.:

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

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

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

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

: 4294-57-9
para-methylphenylmagnesium bromide

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

: 201232-91-9
1-[4,6-di-O-(tert-butyldimethylsilyl)-2,3-dideoxy-β-D-erythro-hex-2-enopyranosyl]-4-methylbenzene

Guidance literature:: With 1,2-bis(diphenylphosphino)ethane nickel(II) chloride; In tetrahydrofuran; at -40 ℃; for 2h;
DOI:10.1021/jo9714674

Reference yield:

: 201233-15-0
(2R,3S,6R)-6-(4-tert-Butyl-phenoxy)-2-hydroxymethyl-3,6-dihydro-2H-pyran-3-ol

: 201232-91-9
1-[4,6-di-O-(tert-butyldimethylsilyl)-2,3-dideoxy-β-D-erythro-hex-2-enopyranosyl]-4-methylbenzene

Guidance literature:: Multi-step reaction with 2 steps

1: imidazole / dimethylformamide / 48 h / Ambient temperature

2: 83 percent / NiCl₂(dppe) / tetrahydrofuran / 2 h / -40 °C

With 1H-imidazole; 1,2-bis(diphenylphosphino)ethane nickel(II) chloride; In tetrahydrofuran; N,N-dimethyl-formamide;
DOI:10.1021/jo9714674

Reference yield:

: 171082-23-8
4-t-butylphenyl4, 6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside

: 201232-91-9
1-[4,6-di-O-(tert-butyldimethylsilyl)-2,3-dideoxy-β-D-erythro-hex-2-enopyranosyl]-4-methylbenzene

Guidance literature:: Multi-step reaction with 3 steps

1: CH₃ONa / methanol / 1 h / 25 °C

2: imidazole / dimethylformamide / 48 h / Ambient temperature

3: 83 percent / NiCl₂(dppe) / tetrahydrofuran / 2 h / -40 °C

With 1H-imidazole; 1,2-bis(diphenylphosphino)ethane nickel(II) chloride; sodium methylate; In tetrahydrofuran; methanol; N,N-dimethyl-formamide;
DOI:10.1021/jo9714674