N-[1-acetoxy-4-phenyl-3-butene-2-yl] 4,5,6,8-tetra-O-acetyl-3,7-anhydro-2-deoxy-D-glycero-D-gulo-octonoyl amide

Base Information

Chemical Name:N-[1-acetoxy-4-phenyl-3-butene-2-yl] 4,5,6,8-tetra-O-acetyl-3,7-anhydro-2-deoxy-D-glycero-D-gulo-octonoyl amide
CAS No.:312521-56-5
Molecular Formula:C₂₈H₃₅NO₁₂
Molecular Weight:577.585
Hs Code.:

Synonyms:N-[1-acetoxy-4-phenyl-3-butene-2-yl] 4,5,6,8-tetra-O-acetyl-3,7-anhydro-2-deoxy-D-glycero-D-gulo-octonoyl amide

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Chemical Property of N-[1-acetoxy-4-phenyl-3-butene-2-yl] 4,5,6,8-tetra-O-acetyl-3,7-anhydro-2-deoxy-D-glycero-D-gulo-octonoyl amide

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Technology Process of N-[1-acetoxy-4-phenyl-3-butene-2-yl] 4,5,6,8-tetra-O-acetyl-3,7-anhydro-2-deoxy-D-glycero-D-gulo-octonoyl amide

There total 4 articles about N-[1-acetoxy-4-phenyl-3-butene-2-yl] 4,5,6,8-tetra-O-acetyl-3,7-anhydro-2-deoxy-D-glycero-D-gulo-octonoyl amide 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: 84.0%

: 77838-20-1
4,5,6,8-tetra-O-acetyl-3,7-anhydro-2-deoxy-D-glycero-D-gulo-octonoyl chloride

: 312521-55-4
(E)-1-acetoxy-2-t-butoxycarbonylamido-4-phenyl-3-butene

: 312521-56-5
N-[1-acetoxy-4-phenyl-3-butene-2-yl] 4,5,6,8-tetra-O-acetyl-3,7-anhydro-2-deoxy-D-glycero-D-gulo-octonoyl amide

Guidance literature:: (E)-1-acetoxy-2-t-butoxycarbonylamido-4-phenyl-3-butene; With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 1.5h;

4,5,6,8-tetra-O-acetyl-3,7-anhydro-2-deoxy-D-glycero-D-gulo-octonoyl chloride; With pyridine; In dichloromethane; at 20 ℃; for 24h;
DOI:10.1016/S0957-4166(00)00294-9

Reference yield:

: 34010-29-2
2-((2S,3S,4R,5R,6R)-3,4,5-triacetoxy-6-(acetoxymethyl)tetrahydro-2H-pyran-2-yl)acetic acid

: 312521-56-5
N-[1-acetoxy-4-phenyl-3-butene-2-yl] 4,5,6,8-tetra-O-acetyl-3,7-anhydro-2-deoxy-D-glycero-D-gulo-octonoyl amide

Guidance literature:: Multi-step reaction with 2 steps

1.1: thionyl chloride / 2 h / 80 °C

2.1: CF₃CO₂H / CH₂Cl₂ / 1.5 h / 20 °C

2.2: 84 percent / pyridine / CH₂Cl₂ / 24 h / 20 °C

With thionyl chloride; trifluoroacetic acid; In dichloromethane; 1.1: Chlorination / 2.1: Hydrolysis / 2.2: Acylation;
DOI:10.1016/S0957-4166(00)00294-9

Reference yield:

: 132803-75-9
(+/-)-(3E)-2-amino-4-phenylbut-3-en-1-ol

: 312521-56-5
N-[1-acetoxy-4-phenyl-3-butene-2-yl] 4,5,6,8-tetra-O-acetyl-3,7-anhydro-2-deoxy-D-glycero-D-gulo-octonoyl amide

Guidance literature:: Multi-step reaction with 3 steps

1.1: 73 percent / Et₃N / CH₂Cl₂ / 3 h / 20 °C

2.1: 97 percent / pyridine / CH₂Cl₂ / 1.5 h / 20 °C

3.1: CF₃CO₂H / CH₂Cl₂ / 1.5 h / 20 °C

3.2: 84 percent / pyridine / CH₂Cl₂ / 24 h / 20 °C

With pyridine; triethylamine; trifluoroacetic acid; In dichloromethane; 1.1: Acylation / 2.1: Acetylation / 3.1: Hydrolysis / 3.2: Acylation;
DOI:10.1016/S0957-4166(00)00294-9