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

Base Information

• Chemical Name: (6E)-3,6-anhydro-1,2:4,5-bis-O-(1-methylethylidene)-7-deoxy-7-(4-methoxyphenyl)-7-(3-nitrophenyl)-L-gluco-hept-6-enitol
• CAS No.: 1198465-43-8
• Molecular Formula: C₂₆H₂₉NO₈
• Molecular Weight: 483.518

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

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

Chemical Property:

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Technology Process of (6E)-3,6-anhydro-1,2:4,5-bis-O-(1-methylethylidene)-7-deoxy-7-(4-methoxyphenyl)-7-(3-nitrophenyl)-L-gluco-hept-6-enitol

There total 3 articles about (6E)-3,6-anhydro-1,2:4,5-bis-O-(1-methylethylidene)-7-deoxy-7-(4-methoxyphenyl)-7-(3-nitrophenyl)-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: 95.0%

(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) + 4-methoxyphenylboronic acid (5720-07-0) → (6E)-3,6-anhydro-1,2:4,5-bis-O-(1-methylethylidene)-7-deoxy-7-(4-methoxyphenyl)-7-(3-nitrophenyl)-L-gluco-hept-6-enitol (1198465-43-8)

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) → (6E)-3,6-anhydro-1,2:4,5-bis-O-(1-methylethylidene)-7-deoxy-7-(4-methoxyphenyl)-7-(3-nitrophenyl)-L-gluco-hept-6-enitol (1198465-43-8)

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 → (6E)-3,6-anhydro-1,2:4,5-bis-O-(1-methylethylidene)-7-deoxy-7-(4-methoxyphenyl)-7-(3-nitrophenyl)-L-gluco-hept-6-enitol (1198465-43-8)

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:

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

4-methoxyphenylboronic acid

m-nitrobenzene boronic acid

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