1-O-benzoyl-5,6-dideoxy-2,3-O-isopropylidene-α-D-lyxo-5-eno-furanoside

Base Information

• Chemical Name: 1-O-benzoyl-5,6-dideoxy-2,3-O-isopropylidene-α-D-lyxo-5-eno-furanoside
• CAS No.: 73111-63-4
• Molecular Formula: C₁₆H₁₈O₅
• Molecular Weight: 290.316
• Mol file: 73111-63-4.mol

Synonyms:1-O-benzoyl-5,6-dideoxy-2,3-O-isopropylidene-α-D-lyxo-5-eno-furanoside

Chemical Property of 1-O-benzoyl-5,6-dideoxy-2,3-O-isopropylidene-α-D-lyxo-5-eno-furanoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-O-benzoyl-5,6-dideoxy-2,3-O-isopropylidene-α-D-lyxo-5-eno-furanoside

There total 6 articles about 1-O-benzoyl-5,6-dideoxy-2,3-O-isopropylidene-α-D-lyxo-5-eno-furanoside 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: 83.0%

1-O-benzoyl-2,3-O-isopropylidene-α-D-mannofuranoside (57492-90-7) → 1-O-benzoyl-5,6-dideoxy-2,3-O-isopropylidene-α-D-lyxo-5-eno-furanoside (73111-63-4)

Guidance literature:

With 1H-imidazole; iodine; triphenylphosphine; In toluene; Heating;

DOI:10.1080/07328300008544144

Reference yield:

(+)-2,3:5,6-di-O-isopropylidene-α-D-mannofuranos-3-yl benzoate (57526-34-8) → 1-O-benzoyl-5,6-dideoxy-2,3-O-isopropylidene-α-D-lyxo-5-eno-furanoside (73111-63-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: aq. AcOH / 2.25 h / 40 °C

2.1: (EtO)3CH; HOAc / 0.5 h / 80 °C

2.2: triphenylacetic acid / 4 h / 170 °C

With acetic acid; orthoformic acid triethyl ester;

DOI:10.1039/b207509a

Reference yield:

benzoyl chloride (98-88-4) → 1-O-benzoyl-5,6-dideoxy-2,3-O-isopropylidene-α-D-lyxo-5-eno-furanoside (73111-63-4)

Guidance literature:

Multi-step reaction with 3 steps

1: triethylamine / dichloromethane / 2 h / 20 °C

2: Amberlite IR-120 ion-exchange resin / methanol / 48 h / 20 °C

3: triphenylphosphine; 1H-imidazole; iodine / toluene / 1.5 h / Inert atmosphere; Reflux

With 1H-imidazole; iodine; triethylamine; triphenylphosphine; In methanol; dichloromethane; toluene;

DOI:10.1055/a-1730-9857

upstream raw materials:

1-O-benzoyl-2,3-O-isopropylidene-α-D-mannofuranoside

(+)-2,3:5,6-di-O-isopropylidene-α-D-mannofuranos-3-yl benzoate

benzoyl chloride

2,3,5,6-di-O-isopropylidene-D-mannofuranose

Downstream raw materials:

1-O-benzoyl-2,3-O-isopropylidene-α-D-mannofuranoside