2',5-anhydro-3-O-benzyl-6-deoxy-1,2-O-isopropylidene-6-C-[3'S/3'R-benzoyloxy-2'S/2'R-hydroxy-tridecyl]-β-L-idofuranose

Base Information

• Chemical Name: 2',5-anhydro-3-O-benzyl-6-deoxy-1,2-O-isopropylidene-6-C-[3'S/3'R-benzoyloxy-2'S/2'R-hydroxy-tridecyl]-β-L-idofuranose
• CAS No.: 247260-31-7
• Molecular Formula: C₃₆H₅₀O₇
• Molecular Weight: 594.789
• Mol file: 247260-31-7.mol

Synonyms:2',5-anhydro-3-O-benzyl-6-deoxy-1,2-O-isopropylidene-6-C-[3'S/3'R-benzoyloxy-2'S/2'R-hydroxy-tridecyl]-β-L-idofuranose

Chemical Property of 2',5-anhydro-3-O-benzyl-6-deoxy-1,2-O-isopropylidene-6-C-[3'S/3'R-benzoyloxy-2'S/2'R-hydroxy-tridecyl]-β-L-idofuranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2',5-anhydro-3-O-benzyl-6-deoxy-1,2-O-isopropylidene-6-C-[3'S/3'R-benzoyloxy-2'S/2'R-hydroxy-tridecyl]-β-L-idofuranose

There total 8 articles about 2',5-anhydro-3-O-benzyl-6-deoxy-1,2-O-isopropylidene-6-C-[3'S/3'R-benzoyloxy-2'S/2'R-hydroxy-tridecyl]-β-L-idofuranose 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: 94.0%

benzoyl chloride (98-88-4) + 2',5-anhydro-3-O-benzyl-6-deoxy-1,2-O-isopropylidene-6-C-[(2'S,3'S/2'R,3'R) and (2'S,3'R/2'R,3'S)-dihydroxytridecyl]-β-L-idofuranose (247214-70-6) → 2',5-anhydro-3-O-benzyl-6-deoxy-1,2-O-isopropylidene-6-C-[3'S/3'R-benzoyloxy-2'S/2'R-hydroxy-tridecyl]-β-L-idofuranose (247260-31-7)

Guidance literature:

With pyridine; In dichloromethane;

Reference yield:

3-O-benzyl-1,2-O-isopropylidene-1,5-D-xylo-dialdofuranose (23558-05-6) → 2',5-anhydro-3-O-benzyl-6-deoxy-1,2-O-isopropylidene-6-C-[3'S/3'R-benzoyloxy-2'S/2'R-hydroxy-tridecyl]-β-L-idofuranose (247260-31-7)

Guidance literature:

Multi-step reaction with 4 steps

1: diethyl ether / 1 h / 20 °C

2: mCPBA / CH₂Cl₂

3: AcOH / CH₂Cl₂ / 24 h

4: 94 percent / pyridine / CH₂Cl₂

With pyridine; acetic acid; 3-chloro-benzenecarboperoxoic acid; In diethyl ether; dichloromethane; 1: Grignard reaction / 2: Epoxidation / 3: Cyclization / 4: Acylation;

Reference yield:

3-O-benzyl-6-deoxy-1,2-O-isopropylidene-6-C-(tridec-2'-ynyl)-β-L-idofuranose (144489-81-6) → 2',5-anhydro-3-O-benzyl-6-deoxy-1,2-O-isopropylidene-6-C-[3'S/3'R-benzoyloxy-2'S/2'R-hydroxy-tridecyl]-β-L-idofuranose (247260-31-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 74 percent / H₂, quinoline / 10 percent Pd/BaSO₄ / methanol / 760 Torr

2: mCPBA / CH₂Cl₂

3: AcOH / CH₂Cl₂ / 24 h

4: 94 percent / pyridine / CH₂Cl₂

With pyridine; quinoline; hydrogen; acetic acid; 3-chloro-benzenecarboperoxoic acid; Pd-BaSO₄; In methanol; dichloromethane; 1: Reduction / 2: Epoxidation / 3: Cyclization / 4: Acylation;

upstream raw materials:

benzoyl chloride

2',5-anhydro-3-O-benzyl-6-deoxy-1,2-O-isopropylidene-6-C-[(2'S,3'S/2'R,3'R) and (2'S,3'R/2'R,3'S)-dihydroxytridecyl]-β-L-idofuranose

3-O-benzyl-1,2-O-isopropylidene-1,5-D-xylo-dialdofuranose

3-O-benzyl-6-deoxy-1,2-O-isopropylidene-6-C-(tridec-(2'Z)-enyl)-β-L-idofuranose

Downstream raw materials:

2',5-anhydro-6-deoxy-1,2-O-isopropylidene-6-C-[3'S-benzoyloxy-2'S-hydroxy-tridecyl]-β-L-idofuranose

2',5-anhydro-6-deoxy-1,2-O-isopropylidene-6-C-[3'R-benzoyloxy-2'R-hydroxy-tridecyl]-β-L-idofuranose