5-O-Benzoyl-1,2-O-(1-methylethylidene)pentofuranos-3-ulose

Base Information

• Chemical Name: 5-O-Benzoyl-1,2-O-(1-methylethylidene)pentofuranos-3-ulose
• CAS No.: 6698-46-0
• Molecular Formula: C15H16O6
• Molecular Weight: 292.288
• NSC Number: 101766
• DSSTox Substance ID: DTXSID20985789
• Mol file: 6698-46-0.mol

Synonyms:6698-46-0;5-O-Benzoyl-1,2-O-(1-methylethylidene)pentofuranos-3-ulose;NSC101766;NSC 101766;(2,2-dimethyl-6-oxo-3a,6a-dihydrofuro[2,3-d][1,3]dioxol-5-yl)methyl benzoate;5-O-Benzoyl-1,2-O-isopropylidene-alpha-D-erythro-pent-3-ulofuranose;NCIOpen2_006751;SCHEMBL14356276;DTXSID20985789;NSC-101766;A900460;(2,2-Dimethyl-6-oxotetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methyl benzoate

Chemical Property of 5-O-Benzoyl-1,2-O-(1-methylethylidene)pentofuranos-3-ulose

Chemical Property:

• Vapor Pressure: 5.77E-07mmHg at 25°C
• Melting Point: 93-94.5 °C
• Boiling Point: 411°C at 760 mmHg
• Flash Point: 182.4°C
• PSA: 71.06000
• Density: 1.247g/cm³
• LogP: 1.28890
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 4
• Exact Mass: 292.09468823
• Heavy Atom Count: 21
• Complexity: 426

Purity/Quality:

97% ^*data from raw suppliers

5-O-Benzoyl-1,2-O-isopropylidene-3-keto-a-D-xylofuranoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(OC2C(O1)OC(C2=O)COC(=O)C3=CC=CC=C3)C
• Uses: 5-O-Benzoyl-1,2-O-isopropylidene-3-keto-a-D-xylofuranoside (CAS# 6698-46-0) is a key intermediate in the chemical manufacture of D-ribose. Also useful in the preparation of methylated nucleoside derivatives (1)

Technology Process of 5-O-Benzoyl-1,2-O-(1-methylethylidene)pentofuranos-3-ulose

There total 15 articles about 5-O-Benzoyl-1,2-O-(1-methylethylidene)pentofuranos-3-ulose 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%

5-O-benzoyl-α-D-xylofuranose (6022-96-4) → 5-O-benzoyl-1,2-O-isopropylidene-α-D-ribofuranos-3-ulose (6698-46-0)

Guidance literature:

With pyridinium dichromate; acetic anhydride; In dichloromethane; for 2h; Heating;

DOI:10.1021/jo00364a015

Reference yield: 96.0%

oxalyl dichloride (79-37-8) + 5-O-benzoyl-α-D-xylofuranose (6022-96-4) → 5-O-benzoyl-1,2-O-isopropylidene-α-D-ribofuranos-3-ulose (6698-46-0)

Guidance literature:

With triethylamine; In dichloromethane; water; dimethyl sulfoxide;

Reference yield: 86.0%

D-xylofuranose (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) + benzoyl chloride (98-88-4) + acetone (67-64-1) → 5-O-benzoyl-1,2-O-isopropylidene-α-D-ribofuranos-3-ulose (6698-46-0)

Guidance literature:

D-xylofuranose; acetone; With sulfuric acid; sodium carbonate; In water; Inert atmosphere;

benzoyl chloride; With triethylamine; at 0 - 20 ℃; Inert atmosphere;

With dipyridinium dichromate; acetic anhydride; In dichloromethane; Inert atmosphere; Reflux;

DOI:10.1039/c9cc09093b

upstream raw materials:

5-O-benzoyl-α-D-xylofuranose

D-xylose

benzoyl chloride

1,2-O-isopropylidene-α-D-xylose

Downstream raw materials:

(6R)-5t-benzoyloxymethyl-2,2-dimethyl-(3at,6rN,6at)-dihydro-spiro[furo[2,3-d][1,3]dioxole-6,4'-imidazolidine]-2',5'-dione

1,2-isopropylidene-3-C-dimethylphosphono-5-O-benzoyl-α-D-ribofuranose

Benzoic acid (3aR,5R,6R,6aR)-6-cyano-6-hydroxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-ylmethyl ester

5-O-benzoyl-1,2-O-isopropylidene-3-C-<(benzyloxy)methylene>-α-D-ribofuranose