1,5-anhydro-3-O-benzoyl-2-deoxy-4,6-O-isopropylidene-D-arabino-hex-1-enitol

Base Information

• Chemical Name: 1,5-anhydro-3-O-benzoyl-2-deoxy-4,6-O-isopropylidene-D-arabino-hex-1-enitol
• CAS No.: 58871-20-8
• Molecular Formula: C₁₆H₁₈O₅
• Molecular Weight: 290.316

Synonyms:1,5-anhydro-3-O-benzoyl-2-deoxy-4,6-O-isopropylidene-D-arabino-hex-1-enitol

Chemical Property of 1,5-anhydro-3-O-benzoyl-2-deoxy-4,6-O-isopropylidene-D-arabino-hex-1-enitol

Chemical Property:

• Boiling Point: 402.7±45.0 °C(Predicted)
• Density: 1.24±0.1 g/cm3(Predicted)

Purity/Quality:

99% ^*data from raw suppliers

3-O-BENZOYL-4,6-O-ISOPROPYLIDENE-D-GLUCAL 95+% ^*data from reagent suppliers

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Technology Process of 1,5-anhydro-3-O-benzoyl-2-deoxy-4,6-O-isopropylidene-D-arabino-hex-1-enitol

There total 4 articles about 1,5-anhydro-3-O-benzoyl-2-deoxy-4,6-O-isopropylidene-D-arabino-hex-1-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: 67.0%

1,5-anhydro-3-O-benzoyl-2-deoxy-D-arabino-hex-1-enitol (151990-41-9) + 2,2-dimethoxy-propane (77-76-9) → 1,5-anhydro-3-O-benzoyl-2-deoxy-4,6-O-isopropylidene-D-arabino-hex-1-enitol (58871-20-8) + Benzoic acid (2R,3S,4R)-3-hydroxy-2-(1-methoxy-1-methyl-ethoxymethyl)-3,4-dihydro-2H-pyran-4-yl ester

Guidance literature:

With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In acetone; at 0 ℃; for 4.5h;

Reference yield: 58.0%

1,5-anhydro-3-O-benzoyl-2-deoxy-D-arabino-hex-1-enitol (151990-41-9) + 2,2-dimethoxy-propane (77-76-9) → 1,5-anhydro-3-O-benzoyl-2-deoxy-4,6-O-isopropylidene-D-arabino-hex-1-enitol (58871-20-8)

Guidance literature:

With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; for 22h; Ambient temperature;

Reference yield:

Benzoic acid (2R,3S,4R)-2-(tert-butyl-dimethyl-silanyloxymethyl)-3-hydroxy-3,4-dihydro-2H-pyran-4-yl ester (114861-44-8) → 1,5-anhydro-3-O-benzoyl-2-deoxy-4,6-O-isopropylidene-D-arabino-hex-1-enitol (58871-20-8)

Guidance literature:

Multi-step reaction with 2 steps

1: tetrabutylammonium fluoride / tetrahydrofuran / 0 °C

2: 58 percent / 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ) / CH₂Cl₂ / 22 h / Ambient temperature

With tetrabutyl ammonium fluoride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; dichloromethane;

upstream raw materials:

1,5-anhydro-3-O-benzoyl-2-deoxy-D-arabino-hex-1-enitol

2,2-dimethoxy-propane

Benzoic acid (2R,3S,4R)-2-(tert-butyl-dimethyl-silanyloxymethyl)-3-hydroxy-3,4-dihydro-2H-pyran-4-yl ester

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