4-nitrophenyl 4-O-(2'-bromoprop-2'-enyl)-6-O-(tert-butyldimethylsilyl)-2,3-dideoxy-α-D-threo-hex-2-enopyranoside

Base Information

Chemical Name:4-nitrophenyl 4-O-(2'-bromoprop-2'-enyl)-6-O-(tert-butyldimethylsilyl)-2,3-dideoxy-α-D-threo-hex-2-enopyranoside
CAS No.:220758-07-6
Molecular Formula:C₂₁H₃₀BrNO₆Si
Molecular Weight:500.462
Hs Code.:

Synonyms:4-nitrophenyl 4-O-(2'-bromoprop-2'-enyl)-6-O-(tert-butyldimethylsilyl)-2,3-dideoxy-α-D-threo-hex-2-enopyranoside

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Chemical Property of 4-nitrophenyl 4-O-(2'-bromoprop-2'-enyl)-6-O-(tert-butyldimethylsilyl)-2,3-dideoxy-α-D-threo-hex-2-enopyranoside

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Technology Process of 4-nitrophenyl 4-O-(2'-bromoprop-2'-enyl)-6-O-(tert-butyldimethylsilyl)-2,3-dideoxy-α-D-threo-hex-2-enopyranoside

There total 4 articles about 4-nitrophenyl 4-O-(2'-bromoprop-2'-enyl)-6-O-(tert-butyldimethylsilyl)-2,3-dideoxy-α-D-threo-hex-2-enopyranoside 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%

: 273199-63-6
4-nitrophenyl 6-O-(tert-butyldimethylsilyl)-2,3-dideoxy-α-D-threo-hex-2-enopyranoside

: 513-31-5
2-bromoallyl bromide

: 220758-07-6
4-nitrophenyl 4-O-(2'-bromoprop-2'-enyl)-6-O-(tert-butyldimethylsilyl)-2,3-dideoxy-α-D-threo-hex-2-enopyranoside

Guidance literature:: 4-nitrophenyl 6-O-(tert-butyldimethylsilyl)-2,3-dideoxy-α-D-threo-hex-2-enopyranoside; With sodium hydride; In tetrahydrofuran; at 20 ℃; for 2h;

2-bromoallyl bromide; In tetrahydrofuran; at 60 ℃; for 24h;
DOI:10.1080/07328300008544075

Reference yield:

: 90114-67-3
(3S)-2t-hydroxymethyl-6c-(4-nitro-phenoxy)-3,6-dihydro-2H-pyran-3r-ol

: 220758-07-6
4-nitrophenyl 4-O-(2'-bromoprop-2'-enyl)-6-O-(tert-butyldimethylsilyl)-2,3-dideoxy-α-D-threo-hex-2-enopyranoside

Guidance literature:: Multi-step reaction with 3 steps

1.1: Et₃N; imidazole / CH₂Cl₂ / 24 h / 20 °C

2.1: PPh₃; ClCH₂CO₂H / toluene / 0.5 h / 0 °C

2.2: DEAD / toluene / 24.5 h / 0 - 20 °C

2.3: 65 percent / NaOMe / methanol

3.1: NaH / tetrahydrofuran / 2 h / 20 °C

3.2: 60 percent / tetrahydrofuran / 24 h / 60 °C

With 1H-imidazole; sodium hydride; triethylamine; chloroacetic acid; triphenylphosphine; In tetrahydrofuran; dichloromethane; toluene; 1.1: silylation / 2.1: Mitsunobu reaction / 2.2: Mitsunobu reaction / 2.3: Substitution / 3.1: Metallation / 3.2: Alkylation;
DOI:10.1080/07328300008544075

Reference yield:

: 14675-51-5,56196-13-5
p-nitrophenyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside

: 220758-07-6
4-nitrophenyl 4-O-(2'-bromoprop-2'-enyl)-6-O-(tert-butyldimethylsilyl)-2,3-dideoxy-α-D-threo-hex-2-enopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1.1: NaOMe / methanol / 20 °C

2.1: Et₃N; imidazole / CH₂Cl₂ / 24 h / 20 °C

3.1: PPh₃; ClCH₂CO₂H / toluene / 0.5 h / 0 °C

3.2: DEAD / toluene / 24.5 h / 0 - 20 °C

3.3: 65 percent / NaOMe / methanol

4.1: NaH / tetrahydrofuran / 2 h / 20 °C

4.2: 60 percent / tetrahydrofuran / 24 h / 60 °C

With 1H-imidazole; sodium methylate; sodium hydride; triethylamine; chloroacetic acid; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane; toluene; 1.1: Deacetylation / 2.1: silylation / 3.1: Mitsunobu reaction / 3.2: Mitsunobu reaction / 3.3: Substitution / 4.1: Metallation / 4.2: Alkylation;
DOI:10.1080/07328300008544075