(6Z)-3,6-anhydro-1,2:4,5-bis-O-(1-methylethylidene)-7-deoxy-7-(3-nitrophenyl)-7-(2-thienyl)-L-gluco-hept-6-enitol

Base Information

• Chemical Name: (6Z)-3,6-anhydro-1,2:4,5-bis-O-(1-methylethylidene)-7-deoxy-7-(3-nitrophenyl)-7-(2-thienyl)-L-gluco-hept-6-enitol
• CAS No.: 1198465-45-0
• Molecular Formula: C₂₃H₂₅NO₇S
• Molecular Weight: 459.52

Synonyms:(6Z)-3,6-anhydro-1,2:4,5-bis-O-(1-methylethylidene)-7-deoxy-7-(3-nitrophenyl)-7-(2-thienyl)-L-gluco-hept-6-enitol

Chemical Property of (6Z)-3,6-anhydro-1,2:4,5-bis-O-(1-methylethylidene)-7-deoxy-7-(3-nitrophenyl)-7-(2-thienyl)-L-gluco-hept-6-enitol

Chemical Property:

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Safty Information:

• Pictogram(s):  
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Technology Process of (6Z)-3,6-anhydro-1,2:4,5-bis-O-(1-methylethylidene)-7-deoxy-7-(3-nitrophenyl)-7-(2-thienyl)-L-gluco-hept-6-enitol

There total 3 articles about (6Z)-3,6-anhydro-1,2:4,5-bis-O-(1-methylethylidene)-7-deoxy-7-(3-nitrophenyl)-7-(2-thienyl)-L-gluco-hept-6-enitol 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%

thiophene boronic acid (6165-68-0) + (6Z)-3,6-anhydro-1,2:4,5-bis-O-(1-methylethylidene)-7-bromo-7-deoxy-7-(3-nitrophenyl)-L-gluco-hept-6-enitol (1198465-29-0) → (6Z)-3,6-anhydro-1,2:4,5-bis-O-(1-methylethylidene)-7-deoxy-7-(3-nitrophenyl)-7-(2-thienyl)-L-gluco-hept-6-enitol (1198465-45-0)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; trifuran-2-yl-phosphane; potassium carbonate; In 1,2-dimethoxyethane; water; at 85 ℃; for 24h; Inert atmosphere;

DOI:10.1016/j.tetlet.2009.09.019

Reference yield:

m-nitrobenzene boronic acid (13331-27-6) → (6Z)-3,6-anhydro-1,2:4,5-bis-O-(1-methylethylidene)-7-deoxy-7-(3-nitrophenyl)-7-(2-thienyl)-L-gluco-hept-6-enitol (1198465-45-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: potassium carbonate / 1,2-dimethoxyethane; water / 0.17 h

1.2: 24 h / 85 °C

2.1: potassium carbonate / 1,2-dimethoxyethane; water / 0.17 h

2.2: 24 h / 85 °C

With potassium carbonate; In 1,2-dimethoxyethane; water; 1.2: Suzuki coupling / 2.2: Suzuki coupling;

DOI:10.1002/ejoc.201100949

Reference yield:

(3aR,6S,6aR)-4-Dibromomethylene-6-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole → (6Z)-3,6-anhydro-1,2:4,5-bis-O-(1-methylethylidene)-7-deoxy-7-(3-nitrophenyl)-7-(2-thienyl)-L-gluco-hept-6-enitol (1198465-45-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: potassium carbonate / 1,2-dimethoxyethane; water / 0.17 h

1.2: 24 h / 85 °C

2.1: potassium carbonate / 1,2-dimethoxyethane; water / 0.17 h

2.2: 24 h / 85 °C

With potassium carbonate; In 1,2-dimethoxyethane; water; 1.2: Suzuki coupling / 2.2: Suzuki coupling;

DOI:10.1002/ejoc.201100949

upstream raw materials:

thiophene boronic acid

(6Z)-3,6-anhydro-1,2:4,5-bis-O-(1-methylethylidene)-7-bromo-7-deoxy-7-(3-nitrophenyl)-L-gluco-hept-6-enitol

m-nitrobenzene boronic acid

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