1-O-benzyl-3,4-O-(2,3-dimethoxybutane-2,3-diyl)-5a-carba-α-D-manuronic acid

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Chemical Name:1-O-benzyl-3,4-O-(2,3-dimethoxybutane-2,3-diyl)-5a-carba-α-D-manuronic acid
CAS No.:1392067-32-1
Molecular Formula:C₂₀H₂₈O₈
Molecular Weight:396.438
Hs Code.:

Synonyms:1-O-benzyl-3,4-O-(2,3-dimethoxybutane-2,3-diyl)-5a-carba-α-D-manuronic acid

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Chemical Property of 1-O-benzyl-3,4-O-(2,3-dimethoxybutane-2,3-diyl)-5a-carba-α-D-manuronic acid

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Technology Process of 1-O-benzyl-3,4-O-(2,3-dimethoxybutane-2,3-diyl)-5a-carba-α-D-manuronic acid

There total 13 articles about 1-O-benzyl-3,4-O-(2,3-dimethoxybutane-2,3-diyl)-5a-carba-α-D-manuronic 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: 99.0%

: 1392067-18-3
(2S,3S,4aR,5S,7S,8R,8aR)-7-(benzyloxy)-8-hydroxy-2,3-dimethoxy-2,3-dimethyloctahydrobenzo[b][1,4]dioxine-5-carbaldehyde

: 1392067-32-1
1-O-benzyl-3,4-O-(2,3-dimethoxybutane-2,3-diyl)-5a-carba-α-D-manuronic acid

Guidance literature:: With sodium chlorite; sodium dihydrogen phosphate monohydrate; dimethyl sulfoxide; In water; tert-butyl alcohol; at 0 ℃; for 1.5h;
DOI:10.1021/jo301240j

Reference yield:

: 176897-12-4
(2S,3S,4aR,5R,7S,8S,8aR)-5-(hydroxymethyl)-2,3,7-trimethoxy-2,3-dimethylhexahydro-2Hpyrano[3,4-b][1,4]dioxin-8-ol4

: 1392067-32-1
1-O-benzyl-3,4-O-(2,3-dimethoxybutane-2,3-diyl)-5a-carba-α-D-manuronic acid

Guidance literature:: Multi-step reaction with 12 steps

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

2.1: (1S)-(+)-camphorsulfonic acid monohydrate / dichloromethane / 16 h / 20 °C

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

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

5.1: tetrahydrofuran; toluene / 2 h / 0 - 20 °C / Inert atmosphere

6.1: sodium hydride / N,N-dimethyl-formamide / 0.17 h / 0 °C / Inert atmosphere

6.2: 3 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: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 21 h / 20 °C

10.1: pyridine / methanol / 72 h / 60 °C

11.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; water / 2.67 h / 0 - 20 °C

12.1: sodium dihydrogen phosphate monohydrate; dimethyl sulfoxide; sodium chlorite / water; tert-butyl alcohol / 1.5 h / 0 °C

With pyridine; 1H-imidazole; sodium chlorite; sodium dihydrogen phosphate monohydrate; (1S)-(+)-camphorsulfonic acid monohydrate; potassium tert-butylate; dihydrogen peroxide; iodine; sodium hydride; dimethyl sulfoxide; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; sodium hydroxide; palladium dichloride; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; tert-butyl alcohol;
DOI:10.1021/jo301240j

Reference yield:

: 197577-12-1
methyl 6-deoxy-3,4-O-(2,3-dimethoxybutane-2,3-diyl)-6-iodo-α-D-mannoside

: 1392067-32-1
1-O-benzyl-3,4-O-(2,3-dimethoxybutane-2,3-diyl)-5a-carba-α-D-manuronic acid

Guidance literature:: Multi-step reaction with 11 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: tetrahydrofuran; toluene / 2 h / 0 - 20 °C / Inert atmosphere

5.1: sodium hydride / N,N-dimethyl-formamide / 0.17 h / 0 °C / Inert atmosphere

5.2: 3 h / 0 - 20 °C / Inert atmosphere

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

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

8.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 21 h / 20 °C

9.1: pyridine / methanol / 72 h / 60 °C

10.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; water / 2.67 h / 0 - 20 °C

11.1: sodium dihydrogen phosphate monohydrate; dimethyl sulfoxide; sodium chlorite / water; tert-butyl alcohol / 1.5 h / 0 °C

With pyridine; sodium chlorite; sodium dihydrogen phosphate monohydrate; (1S)-(+)-camphorsulfonic acid monohydrate; potassium tert-butylate; dihydrogen peroxide; sodium hydride; dimethyl sulfoxide; 2,3-dicyano-5,6-dichloro-p-benzoquinone; sodium hydroxide; palladium dichloride; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; tert-butyl alcohol;
DOI:10.1021/jo301240j