(1R,3R,4R,5R,8R)-5,8-dibenzyloxy-4-(N-imidazolylthiocarbonyloxy)-3-(thymin-1-yl)-2-oxabicyclo[3.3.0]oct-6-ene

Base Information

• Chemical Name: (1R,3R,4R,5R,8R)-5,8-dibenzyloxy-4-(N-imidazolylthiocarbonyloxy)-3-(thymin-1-yl)-2-oxabicyclo[3.3.0]oct-6-ene
• CAS No.: 557099-63-5
• Molecular Formula: C₃₀H₂₈N₄O₆S
• Molecular Weight: 572.642
• Mol file: 557099-63-5.mol

Synonyms:(1R,3R,4R,5R,8R)-5,8-dibenzyloxy-4-(N-imidazolylthiocarbonyloxy)-3-(thymin-1-yl)-2-oxabicyclo[3.3.0]oct-6-ene

Chemical Property of (1R,3R,4R,5R,8R)-5,8-dibenzyloxy-4-(N-imidazolylthiocarbonyloxy)-3-(thymin-1-yl)-2-oxabicyclo[3.3.0]oct-6-ene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,3R,4R,5R,8R)-5,8-dibenzyloxy-4-(N-imidazolylthiocarbonyloxy)-3-(thymin-1-yl)-2-oxabicyclo[3.3.0]oct-6-ene

There total 1 articles about (1R,3R,4R,5R,8R)-5,8-dibenzyloxy-4-(N-imidazolylthiocarbonyloxy)-3-(thymin-1-yl)-2-oxabicyclo[3.3.0]oct-6-ene 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: 84.0%

1,1'-Thiocarbonyldiimidazole (6160-65-2) + (1R,3R,4R,5R,8R)-5,8-Bis(benzyloxy)-4-hydroxy-3-(thymin-1-yl)-2-oxabicyclo[3.3.0]oct-6-ene (352422-92-5) → (1R,3R,4R,5R,8R)-5,8-dibenzyloxy-4-(N-imidazolylthiocarbonyloxy)-3-(thymin-1-yl)-2-oxabicyclo[3.3.0]oct-6-ene (557099-63-5)

Guidance literature:

In toluene; acetonitrile; at 80 ℃; for 3h;

DOI:10.1039/b210439c

Reference yield: 61.0%

(1R,3R,4R,5R,8R)-5,8-dibenzyloxy-4-(N-imidazolylthiocarbonyloxy)-3-(thymin-1-yl)-2-oxabicyclo[3.3.0]oct-6-ene (557099-63-5) → (1R,3R,5R,8R)-5,8-Bis(benzyloxy)-3-(thymin-1-yl)-2-oxabicyclo[3.3.0]octane (352422-96-9)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In acetonitrile; at 80 ℃; for 22h;

DOI:10.1039/b210439c

Reference yield:

(1R,3R,4R,5R,8R)-5,8-dibenzyloxy-4-(N-imidazolylthiocarbonyloxy)-3-(thymin-1-yl)-2-oxabicyclo[3.3.0]oct-6-ene (557099-63-5) → (1R,3R,5R,6R,7R,8R)-5,8-dibenzyloxy-6,7-dihydroxy-3-(thymin-1-yl)-2-oxabicyclo[3.3.0]octane

Guidance literature:

Multi-step reaction with 2 steps

1: 61 percent / AIBN; Bu₃SnH / acetonitrile / 22 h / 80 °C

2: 34 percent / aq. OsO₄; N-methylmorpholine N-oxide / tetrahydrofuran; 2-methyl-propan-2-ol / 3 h / 50 °C

With osmium(VIII) oxide; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; 4-methylmorpholine N-oxide; In tetrahydrofuran; acetonitrile; tert-butyl alcohol;

DOI:10.1039/b210439c

upstream raw materials:

1,1'-Thiocarbonyldiimidazole

(1R,3R,4R,5R,8R)-5,8-Bis(benzyloxy)-4-hydroxy-3-(thymin-1-yl)-2-oxabicyclo[3.3.0]oct-6-ene

Downstream raw materials:

(1R,3R,5R,8R)-5,8-Bis(benzyloxy)-3-(thymin-1-yl)-2-oxabicyclo[3.3.0]octane