5-O-CARBOMETHOXY-1,2-O-ISOPROPYLIDENE-D-XYLOFURANOSE

Base Information

• Chemical Name: 5-O-CARBOMETHOXY-1,2-O-ISOPROPYLIDENE-D-XYLOFURANOSE
• CAS No.: 5432-33-7
• Molecular Formula: C10H16O7
• Molecular Weight: 248.233
• Mol file: 5432-33-7.mol

Synonyms:Xylofuranose,1,2-O-isopropylidene-, 5-(methyl carbonate), D- (6CI);NSC 18194;1,2-O-Isopropylidene-5-O-methoxycarbonyl-a-D-xylofuranose;5-O-(Methoxycarbonyl)-1,2-O-(1-methylethylidene)pentofuranose;5-O-Carbomethoxy-1,2-O-isopropylidene-D-xylofuranose;

Chemical Property of 5-O-CARBOMETHOXY-1,2-O-ISOPROPYLIDENE-D-XYLOFURANOSE

Chemical Property:

• Vapor Pressure: 2.03E-06mmHg at 25°C
• Refractive Index: 1.467
• Boiling Point: 353.7 °C at 760 mmHg
• PKA: 13.06±0.60(Predicted)
• Flash Point: 134.9 °C
• PSA: 83.45000
• Density: 1.27 g/cm³
• LogP: 0.00670
• Storage Temp.: −20°C

Purity/Quality:

99% ^*data from raw suppliers

5-O-Carbomethoxy-1,2-O-isopropylidene-a-D-xylofuranose ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

Technology Process of 5-O-CARBOMETHOXY-1,2-O-ISOPROPYLIDENE-D-XYLOFURANOSE

There total 2 articles about 5-O-CARBOMETHOXY-1,2-O-ISOPROPYLIDENE-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: 73.0%

5-O-tert-butyldimethylsilyl-1,2-O-isopropylidene-3-O-methoxycarbonyl-α-D-xylofuranoside (1388091-75-5) → 3-hydroxy-5-O-carboxymethyl-1,2-O-(1-methylethylidene)-α-D-xylofuranoside (5432-33-7) + 1,2-O-isopropylidene-α-D-xylose (20031-21-4)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 0.166667h;

DOI:10.1016/j.tet.2012.05.117

Reference yield:

1,2-O-isopropylidene-5-O-(tert-butyl)dimethylsilyl-α-D-xylofuranoside (85951-12-8) → 3-hydroxy-5-O-carboxymethyl-1,2-O-(1-methylethylidene)-α-D-xylofuranoside (5432-33-7) + 1,2-O-isopropylidene-α-D-xylose (20031-21-4)

Guidance literature:

Multi-step reaction with 2 steps

1: pyridine; dmap / 0 - 20 °C / Inert atmosphere

2: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.17 h / 20 °C

With pyridine; dmap; tetrabutyl ammonium fluoride; In tetrahydrofuran;

DOI:10.1016/j.tet.2012.05.117

Reference yield: 100.0%

3-hydroxy-5-O-carboxymethyl-1,2-O-(1-methylethylidene)-α-D-xylofuranoside (5432-33-7) + phenylcarbonochloridothioate (1005-56-7) → 1,2-O-isopropylidene-5-O-methoxycarbonyl-3-O-phenoxythiocarbonyl-α-D-xylofuranose (415704-29-9)

Guidance literature:

With pyridine; dmap; In acetonitrile; at 50 - 60 ℃; for 24h;

upstream raw materials:

5-O-tert-butyldimethylsilyl-1,2-O-isopropylidene-3-O-methoxycarbonyl-α-D-xylofuranoside

1,2-O-isopropylidene-5-O-(tert-butyl)dimethylsilyl-α-D-xylofuranoside

Downstream raw materials:

1,2-O-isopropylidene-5-O-(methoxycarbonyl)-3-O-tosyl-α-D-xylofuranose

3-deoxy-1,2-O-isopropylidene-5-O-p-tolylsulfonyl-β-L-threo-pentofuranose

Methanesulfonic acid (2R,3S,4R,5R)-5-(2-amino-6-methoxy-purin-9-yl)-2-methoxycarbonyloxymethyl-4-phenoxythiocarbonyloxy-tetrahydro-furan-3-yl ester

3-Trifluoromethyl-benzoic acid (2R,3R,4S,5R)-2-(2-amino-6-methoxy-purin-9-yl)-4-methanesulfonyloxy-5-methoxycarbonyloxymethyl-tetrahydro-furan-3-yl ester

Refernces