(2R,3S,4S)-2,3,5-Tris(benzyloxy)pentane-1,4-diol

Base Information

• Chemical Name: (2R,3S,4S)-2,3,5-Tris(benzyloxy)pentane-1,4-diol
• CAS No.: 131897-00-2
• Molecular Formula: C26H30O5
• Molecular Weight: 422.51
• DSSTox Substance ID: DTXSID90551152
• Wikidata: Q82430675
• Mol file: 131897-00-2.mol

Synonyms:131897-00-2;(2R,3S,4S)-2,3,5-Tris(benzyloxy)pentane-1,4-diol;(2R,3S,4S)-2,3,5-tris(phenylmethoxy)pentane-1,4-diol;1,3,4-tri-O-benzyl-D-ribitol;DTXSID90551152

Chemical Property of (2R,3S,4S)-2,3,5-Tris(benzyloxy)pentane-1,4-diol

Chemical Property:

• PSA: 68.15000
• LogP: 3.72720
• Storage Temp.: 2-8°C
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 13
• Exact Mass: 422.20932405
• Heavy Atom Count: 31
• Complexity: 441

Purity/Quality:

97% ^*data from raw suppliers

(2R,3S,4S)-2,3,5-Tris(benzyloxy)pentane-1,4-diol 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1=CC=C(C=C1)COCC(C(C(CO)OCC2=CC=CC=C2)OCC3=CC=CC=C3)O
• Isomeric SMILES: C1=CC=C(C=C1)COC[C@@H]([C@@H]([C@@H](CO)OCC2=CC=CC=C2)OCC3=CC=CC=C3)O

Technology Process of (2R,3S,4S)-2,3,5-Tris(benzyloxy)pentane-1,4-diol

There total 15 articles about (2R,3S,4S)-2,3,5-Tris(benzyloxy)pentane-1,4-diol 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: 87.0%

2,3,5-tri-O-benzyl-α-L-ribofuranose (16838-89-4,17073-88-0,60933-68-8,60933-69-9,73068-66-3,89361-52-4,89615-42-9,89615-45-2,96192-07-3) → 1,3,4-tri-O-benzyl-D-ribitol (131897-00-2)

Guidance literature:

With sodium tetrahydroborate; In ethanol; at 50 ℃; for 1h;

Reference yield:

4-Nitro-benzoic acid (1S,2R,3R)-2,3-bis-benzyloxy-1-benzyloxymethyl-4-(tert-butyl-dimethyl-silanyloxy)-butyl ester → 1,3,4-tri-O-benzyl-D-ribitol (131897-00-2)

Guidance literature:

4-Nitro-benzoic acid (1S,2R,3R)-2,3-bis-benzyloxy-1-benzyloxymethyl-4-(tert-butyl-dimethyl-silanyloxy)-butyl ester; With sodium methylate; In methanol; at 20 ℃; for 1h;

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 1.5h;

DOI:10.1016/j.carres.2005.09.004

Reference yield:

2,3,5-tri-O-benzyl-D-lyxitol (122565-72-4) → 1,3,4-tri-O-benzyl-D-ribitol (131897-00-2)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 93 percent / imidazole / dimethylformamide / 0.5 h / 0 °C

2.1: PPh₃; diisopropylazodicarboxylate / tetrahydrofuran / 22 h / 20 °C

3.1: NaOMe / methanol / 1 h / 20 °C

3.2: 2.80 g / tetrabutylammonium fluoride / tetrahydrofuran / 1.5 h / 20 °C

With 1H-imidazole; di-isopropyl azodicarboxylate; sodium methylate; triphenylphosphine; In tetrahydrofuran; methanol; N,N-dimethyl-formamide;

DOI:10.1016/j.carres.2005.09.004

upstream raw materials:

2,3,5-tri-O-benzyl-α-L-ribofuranose

2,3,5-tri-O-benzyl-D-lyxitol

2,3,5-tri-O-benzyl-1-O-tert-butyldimethylsilyl-D-lyxitol

2,3,5-tri-O-benzyl-D-lyxofuranoside

Downstream raw materials:

1,4-anhydro-2,3,5-tri-O-benzyl-4-thio-D-lyxitol

2,3,5-tri-O-benzyl-α-L-ribofuranose

1,3,4-tri-O-benzyl-2-O-<2-O-(benzyloxymethyl)-5-O-(dimethoxytrityl)-β-D-ribofuranosyl>-5-O-(dimethoxytrityl)-D-ribitol