1-(2',3',5'-tri-O-benzyl-β-D-ribofuranosyl)-2-phenylacetylene

Base Information

• Chemical Name: 1-(2',3',5'-tri-O-benzyl-β-D-ribofuranosyl)-2-phenylacetylene
• CAS No.: 113889-66-0
• Molecular Formula: C₃₄H₃₂O₄
• Molecular Weight: 504.626
• Mol file: 113889-66-0.mol

Synonyms:1-(2',3',5'-tri-O-benzyl-β-D-ribofuranosyl)-2-phenylacetylene

Chemical Property of 1-(2',3',5'-tri-O-benzyl-β-D-ribofuranosyl)-2-phenylacetylene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-(2',3',5'-tri-O-benzyl-β-D-ribofuranosyl)-2-phenylacetylene

There total 9 articles about 1-(2',3',5'-tri-O-benzyl-β-D-ribofuranosyl)-2-phenylacetylene 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: 93.0%

(2R,3R,4R,5R)-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)tetrahydrofuran-2-carboxylic acid (42890-06-2) + phenylacetylene (536-74-3) → 1-(2',3',5'-tri-O-benzyl-β-D-ribofuranosyl)-2-phenylacetylene (113889-66-0)

Guidance literature:

With [4,4′-bis(1,1-dimethylethyl)-2,2′-bipyridine-N1,N1′]bis{3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-κN]phenyl-κC}iridium(III) hexafluorophosphate; (1R,2R)-1,2-diaminocyclohexane; cesium acetate; copper diacetate; In N,N-dimethyl acetamide; at 20 ℃; for 24h; diastereoselective reaction; Irradiation;

DOI:10.1021/acscatal.1c01600

Reference yield: 79.0%

1-(2,3,5-Tri-O-benzyl)-D-ribofuranosylcarboxylic acid (42890-06-2,136520-25-7,138809-95-7) + 1-Phenylethynyl-1H-1λ3-benzo[d][1,2]iodoxol-3-one → 1-(2',3',5'-tri-O-benzyl-β-D-ribofuranosyl)-2-phenylacetylene (113889-66-0)

Guidance literature:

With [Ir(2-(2,4-difluorophenyl)-4-(trifluoromethyl)pyridine)₂(5,5'-bis(trifluoromethyl)-2,2'-bipyridine)]PF₆; potassium carbonate; In dichloromethane; at 40 ℃; for 4h; stereoselective reaction; Schlenk technique; Irradiation; Inert atmosphere; Sealed tube; Green chemistry;

DOI:10.1002/cjoc.202100438

Reference yield: 39.0%

(2R,3R,4S,5R)-1,3,4-tribenzoxy-7-phenylhept-6-yne-2,5-diol (935693-85-9) → 1-(2',3',5'-tri-O-benzyl-β-D-ribofuranosyl)-2-phenylacetylene (113889-66-0)

Guidance literature:

With pyridine; p-toluenesulfonyl chloride; at 60 ℃; for 3h;

DOI:10.1055/s-2007-968030

upstream raw materials:

(2R,3R,4R,5S)-3,4-Bis-benzyloxy-2-benzyloxymethyl-5-bromo-tetrahydro-furan

(2R,3R,4S,5R)-1,3,4-tribenzoxy-7-phenylhept-6-yne-2,5-diol

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

phenylacetylene

Downstream raw materials:

2,5-anhydro-1,3,4,6-tetra-O-benzyl-meso-allitol

(2',3',5'-tri-O-benzyl-β-D-ribofuranosyl)methyl alcohol

1-(1-phenyl-2(Z)-ethylene)-2,3,5-tri-O-benzyl-β-D-ribose