3-O-benzoyl-5-deoxy-1,2-O-isopropylidene-α-D-xylo-hexofuranose

Base Information

• Chemical Name: 3-O-benzoyl-5-deoxy-1,2-O-isopropylidene-α-D-xylo-hexofuranose
• CAS No.: 124572-45-8
• Molecular Formula: C₁₆H₂₀O₆
• Molecular Weight: 308.331
• Mol file: 124572-45-8.mol

Synonyms:3-O-benzoyl-5-deoxy-1,2-O-isopropylidene-α-D-xylo-hexofuranose

Chemical Property of 3-O-benzoyl-5-deoxy-1,2-O-isopropylidene-α-D-xylo-hexofuranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-O-benzoyl-5-deoxy-1,2-O-isopropylidene-α-D-xylo-hexofuranose

There total 6 articles about 3-O-benzoyl-5-deoxy-1,2-O-isopropylidene-α-D-xylo-hexofuranose 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: 19.1%

Benzoic acid (3aR,5R,6S,6aR)-2,2-dimethyl-5-((R)-2-thioxo-[1,3]dioxolan-4-yl)-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester (182412-45-9) → 3-O-benzoyl-5-deoxy-1,2-O-isopropylidene-α-D-xylo-hexofuranose (124572-45-8) + Benzoic acid (3aR,5S,6S,6aR)-2,2-dimethyl-5-((S)-2-oxo-[1,3]oxathiolan-5-yl)-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester (182412-49-3) + Benzoic acid (3aR,5S,6R,6aR)-2,2-dimethyl-5-((S)-2-oxo-[1,3]oxathiolan-4-yl)-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester (182412-42-6) + 3-O-benzoyl-5,6-O-carbonyl-1,2-isopropylidene-5-thio-α-D-glucofuranose (182412-41-5)

Guidance literature:

With bis(tri-n-butyltin); In benzene; at 10 - 15 ℃; for 4h; Further byproducts given; Irradiation;

Reference yield:

1,2-di-O-isopropylidene-5,6-O-thiocarbonyl-α-D-glucofuranose (2816-87-7) → 3-O-benzoyl-5-deoxy-1,2-O-isopropylidene-α-D-xylo-hexofuranose (124572-45-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 89 percent / pyridine

2: 8.6 percent / (Bu₃Sn)2 / benzene / 4 h / 10 - 15 °C / Irradiation

With pyridine; bis(tri-n-butyltin); In benzene;

Reference yield:

1,2-O-isopropylidene-α-D-glucofuranose (18549-40-1) → 3-O-benzoyl-5-deoxy-1,2-O-isopropylidene-α-D-xylo-hexofuranose (124572-45-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) Bu₂SnO / 1.) MeOH, reflux, 3 h, 2.) dioxane, from 5 deg C to 10 deg C, 1 h

2: 89 percent / pyridine

3: 8.6 percent / (Bu₃Sn)2 / benzene / 4 h / 10 - 15 °C / Irradiation

With pyridine; bis(tri-n-butyltin); di(n-butyl)tin oxide; In benzene;

upstream raw materials:

Benzoic acid (3aR,5R,6S,6aR)-2,2-dimethyl-5-((R)-2-thioxo-[1,3]dioxolan-4-yl)-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester

1,2-di-O-isopropylidene-5,6-O-thiocarbonyl-α-D-glucofuranose

1,2-O-isopropylidene-α-D-glucofuranose

benzoyl cyanide

Downstream raw materials:

3-O-benzoyl-5-deoxy-1,2-O-isopropylidene-6-O-trityl-α-D-xylo-hexofuranose

3-O-benzoyl-5-deoxy-1,2-O-isopropylidene-6-O-trityl-α-D-ribo-hexofuranose

1-(2-O-acetyl-3-O-benzoyl-5,6-dideoxy-6-diethylphosphono-β-D-ribo-hexofuranosyl)uracil

Benzoic acid (2R,3R,4R,5R)-4-acetoxy-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-(2-phosphono-ethyl)-tetrahydro-furan-3-yl ester