((2R,3S,4S,5R)-3,4-dihydroxy-5-(tosyloxymethyl)tetrahydrofuran-2-yl)methyl benzoate

Base Information

• Chemical Name: ((2R,3S,4S,5R)-3,4-dihydroxy-5-(tosyloxymethyl)tetrahydrofuran-2-yl)methyl benzoate
• CAS No.: 1352744-34-3
• Molecular Formula: C₂₀H₂₂O₈S
• Molecular Weight: 422.456
• Mol file: 1352744-34-3.mol

Synonyms:((2R,3S,4S,5R)-3,4-dihydroxy-5-(tosyloxymethyl)tetrahydrofuran-2-yl)methyl benzoate

Chemical Property of ((2R,3S,4S,5R)-3,4-dihydroxy-5-(tosyloxymethyl)tetrahydrofuran-2-yl)methyl benzoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ((2R,3S,4S,5R)-3,4-dihydroxy-5-(tosyloxymethyl)tetrahydrofuran-2-yl)methyl benzoate

There total 1 articles about ((2R,3S,4S,5R)-3,4-dihydroxy-5-(tosyloxymethyl)tetrahydrofuran-2-yl)methyl benzoate 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: 53.0%

p-toluenesulfonyl chloride (98-59-9) + 1-O-benzoyl-2,5-anhydro-D-mannitol → ((2R,3S,4S,5R)-3,4-dihydroxy-5-(tosyloxymethyl)tetrahydrofuran-2-yl)methyl benzoate (1352744-34-3)

Guidance literature:

With pyridine; at 22 ℃; Cooling with ice;

DOI:10.1016/j.tet.2011.10.067

Reference yield: 80.0%

((2R,3S,4S,5R)-3,4-dihydroxy-5-(tosyloxymethyl)tetrahydrofuran-2-yl)methyl benzoate (1352744-34-3) + benzoyl chloride (98-88-4) → (2R,3R,4R,5R)-2-(benzoyloxymethyl)-5-(tosyloxymethyl)tetrahydrofuran-3,4-diyl dibenzoate (1352744-35-4)

Guidance literature:

With pyridine; at 22 ℃; Cooling with ice;

DOI:10.1016/j.tet.2011.10.067

Reference yield:

((2R,3S,4S,5R)-3,4-dihydroxy-5-(tosyloxymethyl)tetrahydrofuran-2-yl)methyl benzoate (1352744-34-3) → 1-((2-(((2R,3S,4R,5R)-3-benzoyloxy-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)methyl)-2H-1,2,3-triazol-4-yl)methyl)-5-methylpyrimidine-2,4(1H,3H)-dione

Guidance literature:

Multi-step reaction with 3 steps

1: pyridine / 22 °C / Cooling with ice

2: 1,8-diazabicyclo[5.4.0]undec-7-ene / N,N-dimethyl-formamide / 24 h / 20 - 22 °C

3: ammonia / methanol / 72 h / 20 - 22 °C

With pyridine; ammonia; 1,8-diazabicyclo[5.4.0]undec-7-ene; In methanol; N,N-dimethyl-formamide;

DOI:10.1016/j.tet.2011.10.067

upstream raw materials:

p-toluenesulfonyl chloride

Downstream raw materials:

(2R,3R,4R,5R)-2-(benzoyloxymethyl)-5-(tosyloxymethyl)tetrahydrofuran-3,4-diyl dibenzoate

1-((1-(((2R,3R,4R,5R)-3,4-dibenzoyloxy-5-(benzoyloxymethyl)tetrahydrofuran-2-yl)methyl)-1H-1,2,3-triazol-4-yl)methyl)-3-(pivaloyloxymethyl)-5-methylpyrimidine-2,4(1H,3H)-dione

1-((2-(((2R,3R,4R,5R)-3,4-dibenzoyloxy-5-(benzoyloxymethyl)tetrahydrofuran-2-yl)methyl)-2H-1,2,3-triazol-4-yl)methyl)-3-(pivaloyloxymethyl)-5-methylpyrimidine-2,4(1H,3H)-dione