1,5-ANHYDRO-4,6-O-BENZYLIDENE-3-DEOXY-D-GLUCITOL

Base Information

• Chemical Name: 1,5-ANHYDRO-4,6-O-BENZYLIDENE-3-DEOXY-D-GLUCITOL
• CAS No.: 152613-20-2
• Molecular Formula: C13H16 O4
• Molecular Weight: 236.268
• Mol file: 152613-20-2.mol

Synonyms:Pyrano[3,2-d]-1,3-dioxin,D-ribo-hexitol deriv.

Chemical Property of 1,5-ANHYDRO-4,6-O-BENZYLIDENE-3-DEOXY-D-GLUCITOL

Chemical Property:

• Melting Point: 140-142?C
• PSA: 47.92000
• LogP: 1.25040
• Storage Temp.: -20°C Freezer
• Solubility.: Acetontrile (Slightly), Chloroform (Slightly)

Purity/Quality:

98%Min ^*data from raw suppliers

1,5-Anhydro-4,6-O-benzylidene-3-deoxy-D-glucitol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 1,5-Anhydro-4,6-O-benzylidene-3-deoxy-D-glucitol is used in the preparation of fluorescein-containing Mannitol and Glucitol derivatives as probes for DNA hybridization. An useful synthetic intermediate in the preparation of sugar nucleotides

Technology Process of 1,5-ANHYDRO-4,6-O-BENZYLIDENE-3-DEOXY-D-GLUCITOL

There total 7 articles about 1,5-ANHYDRO-4,6-O-BENZYLIDENE-3-DEOXY-D-GLUCITOL 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: 80.0%

1,5-anhydro-4,6-O-benzylidene-3-deoxy-2-O-toluoyl-D-ribo-hexitol (149312-19-6) → (4aR,7R,8aS)-2-phenylhexahydropyrano[3,2-d][1,3]dioxin-7-ol (152613-20-2)

Guidance literature:

With sodium methylate; In methanol; for 4h; Ambient temperature;

DOI:10.1021/jm00066a013

Reference yield:

(4aR,7S,8R,8aS)-2-phenylhexahydropyrano[3,2-d][1,3]dioxine-7,8-diol (65190-39-8) → (4aR,7R,8aS)-2-phenylhexahydropyrano[3,2-d][1,3]dioxin-7-ol (152613-20-2)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) dibutyltin oxide / 1.) benzene, reflux, 16 h, 2.) dioxane, RT, 5 h

2: 4-(dimethylamino)pyridine (DMAP) / CH₂Cl₂ / 1 h / Ambient temperature

3: CH₂Cl₂ / 2 h / Ambient temperature

4: tri-n-butyltin hydride, 2,2'-azobis(2-methylpropionitrile) / toluene / 80 °C

5: 80 percent / NaOMe / methanol / 4 h / Ambient temperature

With dmap; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; sodium methylate; di(n-butyl)tin oxide; In methanol; dichloromethane; toluene;

DOI:10.1021/jm00066a013

Reference yield:

1,5-anhydro-4,6-O-benzylidene-2-O-(p-toluoyl)-D-glucitol (156715-23-0) → (4aR,7R,8aS)-2-phenylhexahydropyrano[3,2-d][1,3]dioxin-7-ol (152613-20-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 4-(dimethylamino)pyridine (DMAP) / CH₂Cl₂ / 1 h / Ambient temperature

2: CH₂Cl₂ / 2 h / Ambient temperature

3: tri-n-butyltin hydride, 2,2'-azobis(2-methylpropionitrile) / toluene / 80 °C

4: 80 percent / NaOMe / methanol / 4 h / Ambient temperature

With dmap; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; sodium methylate; In methanol; dichloromethane; toluene;

DOI:10.1021/jm00066a013

upstream raw materials:

1,5-anhydro-4,6-O-benzylidene-3-deoxy-2-O-toluoyl-D-ribo-hexitol

(4aR,7S,8R,8aS)-2-phenylhexahydropyrano[3,2-d][1,3]dioxine-7,8-diol

1,5-anhydro-4,6-O-benzylidene-2-O-(p-toluoyl)-D-glucitol

1,5-anhydro-D-glucitol

Downstream raw materials:

3-Benzoyl-5-iodo-1-((4aR,7S,8aS)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-1H-pyrimidine-2,4-dione

3-Benzoyl-5-ethyl-1-((4aR,7S,8aS)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-1H-pyrimidine-2,4-dione

3-Benzoyl-1-((4aR,7S,8aS)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-1H-pyrimidine-2,4-dione

3-Benzoyl-5-fluoro-1-((4aR,7S,8aS)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-1H-pyrimidine-2,4-dione

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