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

Base Information

Chemical Name:1-[5,6-di-O-(tert-butyldimethylsilyl)-2,3-dideoxy-β-D-erythro-hex-2-enopyranosyl]-4-chlorobenzene
CAS No.:201233-00-3
Molecular Formula:C₂₄H₄₁ClO₃Si₂
Molecular Weight:469.212
Hs Code.:

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

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

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

There total 4 articles about 1-[5,6-di-O-(tert-butyldimethylsilyl)-2,3-dideoxy-β-D-erythro-hex-2-enopyranosyl]-4-chlorobenzene 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: 60.0%

: 873-77-8
(4-chlorphenyl)magnesium bromide

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

: 201233-00-3
1-[5,6-di-O-(tert-butyldimethylsilyl)-2,3-dideoxy-β-D-erythro-hex-2-enopyranosyl]-4-chlorobenzene

Guidance literature:: With 1,2-bis(diphenylphosphino)ethane nickel(II) chloride; In tetrahydrofuran; at 10 ℃; for 2h;
DOI:10.1021/jo9714674

Reference yield: 60.0%

: 106-39-8
bromochlorobenzene

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

: 201233-00-3
1-[5,6-di-O-(tert-butyldimethylsilyl)-2,3-dideoxy-β-D-erythro-hex-2-enopyranosyl]-4-chlorobenzene

Guidance literature:: bromochlorobenzene; 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:

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

: 201233-00-3
1-[5,6-di-O-(tert-butyldimethylsilyl)-2,3-dideoxy-β-D-erythro-hex-2-enopyranosyl]-4-chlorobenzene

Guidance literature:: Multi-step reaction with 3 steps

1: CH₃ONa / methanol / 1 h / 25 °C

2: imidazole / dimethylformamide / 48 h / Ambient temperature

3: 60 percent / NiCl₂(dppe) / tetrahydrofuran / 2 h / 10 °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