3,5-O-(S)[2-((R)-2-benzoyloxy-1-hydroxyethyl)benzylidene]-1,2-O-isopropylidene-α-D-xylofuranose

Base Information

Chemical Name:3,5-O-(S)[2-((R)-2-benzoyloxy-1-hydroxyethyl)benzylidene]-1,2-O-isopropylidene-α-D-xylofuranose
CAS No.:549513-44-2
Molecular Formula:C₂₄H₂₆O₈
Molecular Weight:442.466
Hs Code.:

Synonyms:3,5-O-(S)[2-((R)-2-benzoyloxy-1-hydroxyethyl)benzylidene]-1,2-O-isopropylidene-α-D-xylofuranose

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Chemical Property of 3,5-O-(S)[2-((R)-2-benzoyloxy-1-hydroxyethyl)benzylidene]-1,2-O-isopropylidene-α-D-xylofuranose

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Technology Process of 3,5-O-(S)[2-((R)-2-benzoyloxy-1-hydroxyethyl)benzylidene]-1,2-O-isopropylidene-α-D-xylofuranose

There total 5 articles about 3,5-O-(S)[2-((R)-2-benzoyloxy-1-hydroxyethyl)benzylidene]-1,2-O-isopropylidene-α-D-xylofuranose 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: 72.0%

: 98-88-4
benzoyl chloride

: 446242-24-6
3,5-O-(S)[2-((R)-1,2-dihydroxyethyl)benzylidene]-1,2-O-isopropylidene-α-D-xylofuranose

: 549513-44-2
3,5-O-(S)[2-((R)-2-benzoyloxy-1-hydroxyethyl)benzylidene]-1,2-O-isopropylidene-α-D-xylofuranose

Guidance literature:: With triethylamine; In toluene; at -20 ℃; for 12h;
DOI:10.1081/CAR-120019011

Reference yield:

: 20031-21-4
1,2-O-isopropylidene-α-D-xylose

: 549513-44-2
3,5-O-(S)[2-((R)-2-benzoyloxy-1-hydroxyethyl)benzylidene]-1,2-O-isopropylidene-α-D-xylofuranose

Guidance literature:: Multi-step reaction with 4 steps

1.1: p-TSA / tetrahydrofuran

2.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / 0 - 20 °C

2.2: 69 percent / tetrahydrofuran; hexane / 1 h / 0 - 20 °C

3.1: 78 percent / AD-mix β / 2-methyl-propan-2-ol; H2O / 10 h / 0 °C

4.1: 72 percent / triethylamine / toluene / 12 h / -20 °C

With n-butyllithium; toluene-4-sulfonic acid; 1,4-bis(9-O-dihydroquinidine)phthalazine; triethylamine; In tetrahydrofuran; hexane; water; toluene; tert-butyl alcohol; 2.2: Wittig reaction / 3.1: Sharpless asymmetric dihydroxylation;
DOI:10.1081/CAR-120019011

Reference yield:

: 337903-22-7
3,5-O-(2-formylbenzylidene)-1,2-O-isopropylidene-α-D-xylofuranose

: 549513-44-2
3,5-O-(S)[2-((R)-2-benzoyloxy-1-hydroxyethyl)benzylidene]-1,2-O-isopropylidene-α-D-xylofuranose

Guidance literature:: Multi-step reaction with 3 steps

1.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / 0 - 20 °C

1.2: 69 percent / tetrahydrofuran; hexane / 1 h / 0 - 20 °C

2.1: 78 percent / AD-mix β / 2-methyl-propan-2-ol; H2O / 10 h / 0 °C

3.1: 72 percent / triethylamine / toluene / 12 h / -20 °C

With n-butyllithium; 1,4-bis(9-O-dihydroquinidine)phthalazine; triethylamine; In tetrahydrofuran; hexane; water; toluene; tert-butyl alcohol; 1.2: Wittig reaction / 2.1: Sharpless asymmetric dihydroxylation;
DOI:10.1081/CAR-120019011