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

Base Information

Chemical Name:4-nitrophenyl 6-O-(tert-butyldimethylsilyl)-2,3-dideoxy-α-D-threo-hex-2-enopyranoside
CAS No.:273199-63-6
Molecular Formula:C₁₈H₂₇NO₆Si
Molecular Weight:381.501
Hs Code.:

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

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

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

There total 3 articles about 4-nitrophenyl 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: 65.0%

: 157430-17-6
4-nitrophenyl 6-O-(tert-butyldimethylsilyl)-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside

: 273199-63-6
4-nitrophenyl 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-erythro-hex-2-enopyranoside; With chloroacetic acid; triphenylphosphine; In toluene; at 0 ℃; for 0.5h;

With diethylazodicarboxylate; In toluene; at 0 - 20 ℃; for 24.5h;

With sodium methylate; In methanol;
DOI:10.1080/07328300008544075

Reference yield:

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

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

Guidance literature:: Multi-step reaction with 2 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

With 1H-imidazole; triethylamine; chloroacetic acid; triphenylphosphine; In dichloromethane; toluene; 1.1: silylation / 2.1: Mitsunobu reaction / 2.2: Mitsunobu reaction / 2.3: Substitution;
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

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

Guidance literature:: Multi-step reaction with 3 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

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