5-O-Trityl-D-ribofuranose

Base Information

• Chemical Name: 5-O-Trityl-D-ribofuranose
• CAS No.: 53225-58-4
• Molecular Formula: C₂₄H₂₄O₅
• Molecular Weight: 392.452
• Hs Code.: 2932190090
• DSSTox Substance ID: DTXSID60447477
• Nikkaji Number: J859.468F
• Mol file: 53225-58-4.mol

Synonyms:5-O-TRITYL-D-RIBOFURANOSE;53225-58-4;(3R,4S,5R)-5-(trityloxymethyl)oxolane-2,3,4-triol;SCHEMBL3194070;DTXSID60447477

Chemical Property of 5-O-Trityl-D-ribofuranose

Chemical Property:

• PSA: 79.15000
• LogP: 2.43410
• 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:

97% ^*data from raw suppliers

5-O-Trityl-D-ribose ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

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(O4)O)O)O
• Uses: 5-O-Trityl-D-ribose is a protected ribose sugar compound. It is used as a reactant in the preparation of 1,1-dibromo-1-alkenes using the Wittig reaction.

Technology Process of 5-O-Trityl-D-ribofuranose

There total 1 articles about 5-O-Trityl-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: 38.0%

D-Arabinose (10323-20-3) + trityl chloride (76-83-5) → 5-O-trityl-D-arabinose (53225-58-4,67816-38-0,69557-99-9,69558-00-5,69557-98-8)

Guidance literature:

With dmap; triethylamine; In tetrahydrofuran; at 20 ℃; for 1h;

DOI:10.1016/j.tet.2011.11.068

Reference yield: 64.0%

5-O-trityl-D-arabinose (53225-58-4,67816-38-0,69557-99-9,69558-00-5,69557-98-8) → 5-O-trityl-D-arabinitol (1373719-20-0)

Guidance literature:

With sodium tetrahydroborate; In methanol; ethanol; at 0 ℃; for 2h;

DOI:10.1016/j.tet.2011.11.068

Reference yield:

5-O-trityl-D-arabinose (53225-58-4,67816-38-0,69557-99-9,69558-00-5,69557-98-8) → 3-O-allyl-1,2-O-isopropylidene-5-O-triphenylmethyl-β-D-arabinofuranose (139615-45-5)

Guidance literature:

Multi-step reaction with 2 steps

1: p-toluenesulfonic acid / CHCl₃

2: 76 percent / NaH / dimethylformamide

With sodium hydride; toluene-4-sulfonic acid; In chloroform; N,N-dimethyl-formamide;

DOI:10.1246/cl.1992.25

upstream raw materials:

D-Arabinose

trityl chloride

Downstream raw materials:

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

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

5-O-trityl-D-arabinitol

1-O-linoleoyl-5-O-trityl-D-arabinitol