1,6-anhydro-3,4-O-(2,3-dimethoxybutane-2,3-diyl)-2-O-(p-methoxybenzyl)-5a-carba-β-L-guluronic acid

Base Information

• Chemical Name: 1,6-anhydro-3,4-O-(2,3-dimethoxybutane-2,3-diyl)-2-O-(p-methoxybenzyl)-5a-carba-β-L-guluronic acid
• CAS No.: 1392067-46-7
• Molecular Formula: C₂₁H₂₈O₈
• Molecular Weight: 408.449

Synonyms:1,6-anhydro-3,4-O-(2,3-dimethoxybutane-2,3-diyl)-2-O-(p-methoxybenzyl)-5a-carba-β-L-guluronic acid

Chemical Property of 1,6-anhydro-3,4-O-(2,3-dimethoxybutane-2,3-diyl)-2-O-(p-methoxybenzyl)-5a-carba-β-L-guluronic acid

Chemical Property:

Purity/Quality:

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Technology Process of 1,6-anhydro-3,4-O-(2,3-dimethoxybutane-2,3-diyl)-2-O-(p-methoxybenzyl)-5a-carba-β-L-guluronic acid

There total 8 articles about 1,6-anhydro-3,4-O-(2,3-dimethoxybutane-2,3-diyl)-2-O-(p-methoxybenzyl)-5a-carba-β-L-guluronic acid 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: 88.0%

3,4-O-(2,3-dimethoxybutane-2,3-diyl)-2-O-(p-methoxybenzyl)-5a-carba-β-L-gulopyranose (1392067-45-6) → 1,6-anhydro-3,4-O-(2,3-dimethoxybutane-2,3-diyl)-2-O-(p-methoxybenzyl)-5a-carba-β-L-guluronic acid (1392067-46-7)

Guidance literature:

With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; In dichloromethane; at 20 ℃; for 20h; Inert atmosphere;

DOI:10.1021/jo301240j

Reference yield:

(2R,3S,4S,5S,6S)-2-(hydroxymethyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triol (617-04-9) → 1,6-anhydro-3,4-O-(2,3-dimethoxybutane-2,3-diyl)-2-O-(p-methoxybenzyl)-5a-carba-β-L-guluronic acid (1392067-46-7)

Guidance literature:

Multi-step reaction with 9 steps

1.1: (1S)-10-camphorsulfonic acid / methanol / 17 h / Reflux

2.1: triphenylphosphine; 1H-imidazole; iodine / tetrahydrofuran / Reflux

3.1: (1S)-(+)-camphorsulfonic acid monohydrate / dichloromethane / 16 h / 20 °C

4.1: potassium tert-butylate / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere

5.1: palladium dichloride / 1,4-dioxane; water / 3 h / 60 °C / Inert atmosphere

6.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / 0 - 20 °C / Inert atmosphere

6.2: 2 h / 0 - 20 °C / Inert atmosphere

7.1: tetrahydrofuran / 2.5 h / 20 °C / Inert atmosphere

8.1: sodium hydroxide; dihydrogen peroxide / tetrahydrofuran; water / 2 h / 0 - 20 °C / Inert atmosphere

9.1: [bis(acetoxy)iodo]benzene; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical / dichloromethane / 20 h / 20 °C / Inert atmosphere

With 1H-imidazole; n-butyllithium; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; (1S)-(+)-camphorsulfonic acid monohydrate; [bis(acetoxy)iodo]benzene; (1S)-10-camphorsulfonic acid; potassium tert-butylate; dihydrogen peroxide; iodine; triphenylphosphine; sodium hydroxide; palladium dichloride; In tetrahydrofuran; 1,4-dioxane; methanol; hexane; dichloromethane; water; 6.1: |Wittig Olefination;

DOI:10.1021/jo301240j

Reference yield:

methyl 6-deoxy-3,4-O-(2,3-dimethoxybutane-2,3-diyl)-6-iodo-α-D-mannoside (197577-12-1) → 1,6-anhydro-3,4-O-(2,3-dimethoxybutane-2,3-diyl)-2-O-(p-methoxybenzyl)-5a-carba-β-L-guluronic acid (1392067-46-7)

Guidance literature:

Multi-step reaction with 7 steps

1.1: (1S)-(+)-camphorsulfonic acid monohydrate / dichloromethane / 16 h / 20 °C

2.1: potassium tert-butylate / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere

3.1: palladium dichloride / 1,4-dioxane; water / 3 h / 60 °C / Inert atmosphere

4.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / 0 - 20 °C / Inert atmosphere

4.2: 2 h / 0 - 20 °C / Inert atmosphere

5.1: tetrahydrofuran / 2.5 h / 20 °C / Inert atmosphere

6.1: sodium hydroxide; dihydrogen peroxide / tetrahydrofuran; water / 2 h / 0 - 20 °C / Inert atmosphere

7.1: [bis(acetoxy)iodo]benzene; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical / dichloromethane / 20 h / 20 °C / Inert atmosphere

With n-butyllithium; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; (1S)-(+)-camphorsulfonic acid monohydrate; [bis(acetoxy)iodo]benzene; potassium tert-butylate; dihydrogen peroxide; sodium hydroxide; palladium dichloride; In tetrahydrofuran; 1,4-dioxane; hexane; dichloromethane; water; 4.1: |Wittig Olefination;

DOI:10.1021/jo301240j

upstream raw materials:

methyl 6-deoxy-3,4-O-(2,3-dimethoxybutane-2,3-diyl)-6-iodo-α-D-mannoside

(2'S,3'S)-methyl 6-deoxy-2-O-(4-methoxybenzyl)-3,4-O-(2',3'-dimethoxybutane-2',3'-diyl)-6-iodo-α-D-mannopyranoside

6-deoxy-2-O-(p-methoxybenzyl)-3,4-O-(2,3-dimethoxybutane-2,3-diyl)-5a-carba-α-D-lyxo-hex-5-enopyranoside

(2R,3S,4S,5S,6S)-2-(hydroxymethyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triol

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