5-O-(Triphenylmethyl)-alpha-D-ribofuranose

Base Information

• Chemical Name: 5-O-(Triphenylmethyl)-alpha-D-ribofuranose
• CAS No.: 55726-00-6
• Molecular Formula: C₂₄H₂₄O₅
• Molecular Weight: 392.452
• DSSTox Substance ID: DTXSID401282718
• Mol file: 55726-00-6.mol

Synonyms:55726-00-6;5-O-(Triphenylmethyl)-alpha-D-ribofuranose;SCHEMBL3194078;DTXSID401282718;(2S,3R,4S,5R)-5-((trityloxy)methyl)tetrahydrofuran-2,3,4-triol

Chemical Property of 5-O-(Triphenylmethyl)-alpha-D-ribofuranose

Chemical Property:

• XLogP3: 2.7
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 6
• Exact Mass: 392.16237386
• Heavy Atom Count: 29
• Complexity: 448

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C(C2=CC=CC=C2)(C3=CC=CC=C3)OCC4C(C(C(O4)O)O)O
• Isomeric SMILES: C1=CC=C(C=C1)C(C2=CC=CC=C2)(C3=CC=CC=C3)OC[C@@H]4[C@H]([C@H]([C@H](O4)O)O)O

Technology Process of 5-O-(Triphenylmethyl)-alpha-D-ribofuranose

There total 14 articles about 5-O-(Triphenylmethyl)-alpha-D-ribofuranose 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: 78.0%

trityl chloride (76-83-5) + L(+)-arabinose (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) → 5-O-triphenylmethyl-L-arabinofuranose (55726-00-6,72521-12-1,72521-13-2,72521-20-1,72521-21-2,72521-22-3,131285-09-1,131285-24-0)

Guidance literature:

With pyridine; for 24h; Ambient temperature;

DOI:10.1139/v90-347

Reference yield: 70.0%

D-arabinopyranose (28697-53-2) + trityl chloride (76-83-5) → (3S,4S,5R)-5-((trityloxy)methyl)tetrahydrofuran-2,3,4-triol (55726-00-6,72521-12-1,72521-13-2,72521-20-1,72521-21-2,72521-22-3,131285-09-1,131285-24-0)

Guidance literature:

With pyridine; stereospecific reaction;

DOI:10.1016/j.tetlet.2011.05.073

Reference yield: 67.0%

L-arabinose (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) + trityl chloride (76-83-5) → 5-O-triphenylmethyl-L-arabinofuranose (55726-00-6,72521-12-1,72521-13-2,72521-20-1,72521-21-2,72521-22-3,131285-09-1,131285-24-0)

Guidance literature:

With pyridine; dmap; at 60 ℃; for 1h;

DOI:10.1271/bbb.64.2320

upstream raw materials:

D-xylose

trityl chloride

D-arabinofuranose

D-arabinopyranose

Downstream raw materials:

(2R,3R,4R)-2,3-dihydroxy-5-trityloxy-4-pentanolide

1,2-O-isopropylidene-5-O-triphenylmethyl-β-D-arabinofuranose

1,2,3-tri-O-benzoyl-5-O-trityl-α-D-arabinofuranose

C₄₅H₄₂O₅