5-O-benzoyl-3-O-benzyl-1,2-O-isopropylidene-α-D-xylofuranose

Base Information

• Chemical Name: 5-O-benzoyl-3-O-benzyl-1,2-O-isopropylidene-α-D-xylofuranose
• CAS No.: 1611459-79-0
• Molecular Formula: C₂₂H₂₄O₆
• Molecular Weight: 384.429
• Mol file: 1611459-79-0.mol

Synonyms:5-O-benzoyl-3-O-benzyl-1,2-O-isopropylidene-α-D-xylofuranose

Chemical Property of 5-O-benzoyl-3-O-benzyl-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-benzyl-1,2-O-isopropylidene-α-D-xylofuranose

There total 4 articles about 5-O-benzoyl-3-O-benzyl-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: 98.0%

3-O-benzyl-1,2-O-isopropylidene-α-D-xylofuranose (34370-91-7,59358-33-7,68354-70-1,70798-12-8,19139-80-1) + benzoyl chloride (98-88-4) → 5-O-benzoyl-3-O-benzyl-1,2-O-isopropylidene-α-D-xylofuranose (1611459-79-0)

Guidance literature:

With pyridine; dmap; at 0 - 20 ℃; for 1.66667h; Inert atmosphere;

DOI:10.1016/j.tetasy.2014.04.002

Reference yield:

1,2-O-isopropylidene-5-O-trityl-α-D-xylofuranose (20590-53-8) → 5-O-benzoyl-3-O-benzyl-1,2-O-isopropylidene-α-D-xylofuranose (1611459-79-0)

Guidance literature:

Multi-step reaction with 3 steps

1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0 °C / Inert atmosphere

1.2: 0.5 h / 0 - 20 °C / Inert atmosphere

2.1: toluene-4-sulfonic acid / methanol; dichloromethane / 1 h / 20 °C / Inert atmosphere

3.1: dmap; pyridine / 1.67 h / 0 - 20 °C / Inert atmosphere

With pyridine; dmap; sodium hydride; toluene-4-sulfonic acid; In methanol; dichloromethane; N,N-dimethyl-formamide; mineral oil;

DOI:10.1016/j.tetasy.2014.04.002

Reference yield:

1,2-O-isopropylidene-3-O-benzyl-5-O-triphenylmethyl-α-D-xylofuranoside (185541-37-1) → 5-O-benzoyl-3-O-benzyl-1,2-O-isopropylidene-α-D-xylofuranose (1611459-79-0)

Guidance literature:

Multi-step reaction with 2 steps

1: toluene-4-sulfonic acid / methanol; dichloromethane / 1 h / 20 °C / Inert atmosphere

2: dmap; pyridine / 1.67 h / 0 - 20 °C / Inert atmosphere

With pyridine; dmap; toluene-4-sulfonic acid; In methanol; dichloromethane;

DOI:10.1016/j.tetasy.2014.04.002

upstream raw materials:

1,2-O-isopropylidene-5-O-trityl-α-D-xylofuranose

1,2-O-isopropylidene-3-O-benzyl-5-O-triphenylmethyl-α-D-xylofuranoside

3-O-benzyl-1,2-O-isopropylidene-α-D-xylofuranose

benzoyl chloride

Downstream raw materials:

(4R)-4-[(1'R,2'R)-2'-(benzyloxy)-1',3'-dihydroxypropyl]oxazolidin-2-one

(4R)-4-[(1'R,2'R)-2'-(benzyloxy)-1'-hydroxy-3'-(trityloxy)propyl]oxazolidin-2-one

(4R)-3-benzyl-4-[(1'R,2'R)-1',2'-bis(benzyloxy)-3'-(trityloxy)propyl]oxazolidin-2-one

(4R)-3-benzyl-4-[(1'R,2'R)-1',2'-bis(benzyloxy)-3'-hydroxypropyl]oxazolidin-2-one