1,2-O-isopropylidene-3-keto-5-O-benzyl-6-deoxy-6-C-vinyl-α-D-galactofuranose

Base Information

Chemical Name:1,2-O-isopropylidene-3-keto-5-O-benzyl-6-deoxy-6-C-vinyl-α-D-galactofuranose
CAS No.:1352234-69-5
Molecular Formula:C₁₈H₂₂O₅
Molecular Weight:318.37
Hs Code.:

Synonyms:1,2-O-isopropylidene-3-keto-5-O-benzyl-6-deoxy-6-C-vinyl-α-D-galactofuranose

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Chemical Property of 1,2-O-isopropylidene-3-keto-5-O-benzyl-6-deoxy-6-C-vinyl-α-D-galactofuranose

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Technology Process of 1,2-O-isopropylidene-3-keto-5-O-benzyl-6-deoxy-6-C-vinyl-α-D-galactofuranose

There total 10 articles about 1,2-O-isopropylidene-3-keto-5-O-benzyl-6-deoxy-6-C-vinyl-α-D-galactofuranose 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: 90.0%

: 1352234-68-4
1,2-O-isopropylidene-5-O-benzyl-6-deoxy-6-C-vinyl-α-D-galactofuranose

: 1352234-69-5
1,2-O-isopropylidene-3-keto-5-O-benzyl-6-deoxy-6-C-vinyl-α-D-galactofuranose

Guidance literature:: With sodium acetate; pyridinium chlorochromate; In dichloromethane; at 0 - 20 ℃; for 3h;
DOI:10.1021/jo401166q

Reference yield:

: 1352234-51-5
1,2-O-isopropylidene-3-O-(2-naphthylmethyl)-β-L-arabinopentodialdofuranose

: 1352234-69-5
1,2-O-isopropylidene-3-keto-5-O-benzyl-6-deoxy-6-C-vinyl-α-D-galactofuranose

Guidance literature:: Multi-step reaction with 4 steps

1.1: magnesium bromide diethyl etherate / dichloromethane / 0.08 h / -78 °C

1.2: 3 h / 78 °C

2.1: sodium hydride; tetra-(n-butyl)ammonium iodide / N,N-dimethyl-formamide; tetrahydrofuran; mineral oil / 4 h / 0 - 20 °C

3.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; water / 4 h

4.1: pyridinium chlorochromate; sodium acetate / dichloromethane / 3 h / 0 - 20 °C

With magnesium bromide diethyl etherate; sodium acetate; tetra-(n-butyl)ammonium iodide; sodium hydride; pyridinium chlorochromate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; mineral oil; 1.1: |Sakurai Allylation / 1.2: |Sakurai Allylation;
DOI:10.1021/jo401166q

Reference yield:

: 532-20-7,613-83-2,7261-25-8,7687-39-0,13221-22-2,14795-83-6,15761-67-8,20074-49-1,25545-03-3,25545-04-4,32445-75-3,34436-17-4,36441-93-7,36468-53-8,37110-85-3,37388-49-1,38029-69-5,40461-77-6,40461-89-0,41546-19-4,41546-20-7,41546-21-8,41546-26-3,41546-29-6,41546-30-9,41546-31-0,126872-16-0,131064-98-7
L-arabinose

: 1352234-69-5
1,2-O-isopropylidene-3-keto-5-O-benzyl-6-deoxy-6-C-vinyl-α-D-galactofuranose

Guidance literature:: Multi-step reaction with 9 steps

1.1: 1H-imidazole / N,N-dimethyl-formamide / 4 h / 60 °C

2.1: copper(II) sulfate; sulfuric acid / 1 h / 23 °C

3.1: sodium hydride; tetra-(n-butyl)ammonium iodide / N,N-dimethyl-formamide; tetrahydrofuran; mineral oil / 2 h / 0 - 23 °C

4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 4 h / 23 °C

5.1: N-ethyl-N,N-diisopropylamine; sulfur trioxide pyridine complex / dimethyl sulfoxide; dichloromethane / 0.17 h / -20 °C

6.1: magnesium bromide diethyl etherate / dichloromethane / 0.08 h / -78 °C

6.2: 3 h / 78 °C

7.1: sodium hydride; tetra-(n-butyl)ammonium iodide / N,N-dimethyl-formamide; tetrahydrofuran; mineral oil / 4 h / 0 - 20 °C

8.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; water / 4 h

9.1: pyridinium chlorochromate; sodium acetate / dichloromethane / 3 h / 0 - 20 °C

With 1H-imidazole; magnesium bromide diethyl etherate; sulfuric acid; tetrabutyl ammonium fluoride; sodium acetate; sulfur trioxide pyridine complex; tetra-(n-butyl)ammonium iodide; sodium hydride; copper(II) sulfate; N-ethyl-N,N-diisopropylamine; pyridinium chlorochromate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; mineral oil; 5.1: |Parikh-Doering Oxidation / 6.1: |Sakurai Allylation / 6.2: |Sakurai Allylation;
DOI:10.1021/jo401166q