5-O-benzoyl-3-O-(1-imidazolylthiocarbonyl)-1,2-O-isopropylidene-α-D-xylofuranose

Base Information

• Chemical Name: 5-O-benzoyl-3-O-(1-imidazolylthiocarbonyl)-1,2-O-isopropylidene-α-D-xylofuranose
• CAS No.: 160999-15-5
• Molecular Formula: C₁₉H₂₀N₂O₆S
• Molecular Weight: 404.444
• Mol file: 160999-15-5.mol

Synonyms:5-O-benzoyl-3-O-(1-imidazolylthiocarbonyl)-1,2-O-isopropylidene-α-D-xylofuranose

Chemical Property of 5-O-benzoyl-3-O-(1-imidazolylthiocarbonyl)-1,2-O-isopropylidene-α-D-xylofuranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5-O-benzoyl-3-O-(1-imidazolylthiocarbonyl)-1,2-O-isopropylidene-α-D-xylofuranose

There total 2 articles about 5-O-benzoyl-3-O-(1-imidazolylthiocarbonyl)-1,2-O-isopropylidene-α-D-xylofuranose 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: 91.0%

1,1'-Thiocarbonyldiimidazole (6160-65-2) + 5-O-benzoyl-α-D-xylofuranose (6022-96-4) → 5-O-benzoyl-3-O-(1-imidazolylthiocarbonyl)-1,2-O-isopropylidene-α-D-xylofuranose (160999-15-5)

Guidance literature:

In dichloromethane; for 4h; Heating;

DOI:10.1016/S0040-4020(01)85259-5

Reference yield:

1,2-O-isopropylidene-α-D-xylose (20031-21-4) → 5-O-benzoyl-3-O-(1-imidazolylthiocarbonyl)-1,2-O-isopropylidene-α-D-xylofuranose (160999-15-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 76 percent / pyridine / 0.5 h / -20 - 0 °C

2: 91 percent / CH₂Cl₂ / 4 h / Heating

In pyridine; dichloromethane;

DOI:10.1016/S0040-4020(01)85259-5

Reference yield: 93.0%

5-O-benzoyl-3-O-(1-imidazolylthiocarbonyl)-1,2-O-isopropylidene-α-D-xylofuranose (160999-15-5) → [(3aR,5S,6aR)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl]methyl benzoate (4105-29-7)

Guidance literature:

With methyl phosphite; dibenzoyl peroxide; In 1,4-dioxane; for 2.5h; Heating;

DOI:10.1016/j.tetlet.2008.03.079

upstream raw materials:

1,1'-Thiocarbonyldiimidazole

5-O-benzoyl-α-D-xylofuranose

1,2-O-isopropylidene-α-D-xylose

Downstream raw materials:

[(3aR,5S,6aR)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl]methyl benzoate

4(S)-<4-amino-2-oxo-1(2H)-pyrimidinyl>-2(S)-(O-benzoylmethyl)tetrahydrofuran

1,4-anhydro-5-O-benzoyl-3-deoxy-2-O-p-toluenesulfonyl-D-ribitol

2(S)-(O-benzoylmethyl)-4(S)-<4-(1,2,4-triazolyl)-2-oxo-1(2H)-pyrimidinyl>tetrahydrofuran