3-O-(2-O-acetyl-α-L-idopyranosyl)-2,5-anhydro-1,6-di-O-benzoyl-D-mannitol

Base Information

• Chemical Name: 3-O-(2-O-acetyl-α-L-idopyranosyl)-2,5-anhydro-1,6-di-O-benzoyl-D-mannitol
• CAS No.: 735327-12-5
• Molecular Formula: C₂₈H₃₂O₁₃
• Molecular Weight: 576.554
• Mol file: 735327-12-5.mol

Synonyms:3-O-(2-O-acetyl-α-L-idopyranosyl)-2,5-anhydro-1,6-di-O-benzoyl-D-mannitol

Chemical Property of 3-O-(2-O-acetyl-α-L-idopyranosyl)-2,5-anhydro-1,6-di-O-benzoyl-D-mannitol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-O-(2-O-acetyl-α-L-idopyranosyl)-2,5-anhydro-1,6-di-O-benzoyl-D-mannitol

There total 11 articles about 3-O-(2-O-acetyl-α-L-idopyranosyl)-2,5-anhydro-1,6-di-O-benzoyl-D-mannitol 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: 95.0%

3-O-(2-O-acetyl-3-O-benzyl-4,6-O-benzylidene-α-L-idopyranosyl)-2,5-anhydro-1,6-di-O-benzoyl-D-mannitol (735327-02-3) → 3-O-(2-O-acetyl-α-L-idopyranosyl)-2,5-anhydro-1,6-di-O-benzoyl-D-mannitol (735327-12-5)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; water; at 20 ℃; for 6h;

DOI:10.1016/j.carres.2004.03.006

Reference yield:

benzoyl chloride (98-88-4) → 3-O-(2-O-acetyl-α-L-idopyranosyl)-2,5-anhydro-1,6-di-O-benzoyl-D-mannitol (735327-12-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 58 percent / pyridine; CH₂Cl₂ / 0 - 20 °C

2: 81 percent / TfOH; NIS; molecular sieve / CH₂Cl₂ / -40 - 20 °C

3: 95 percent / hydrogen / Pd/C / H₂O; methanol / 6 h / 20 °C

With N-iodo-succinimide; molecular sieve; trifluorormethanesulfonic acid; hydrogen; palladium on activated charcoal; In pyridine; methanol; dichloromethane; water;

DOI:10.1016/j.carres.2004.03.006

Reference yield:

(2R,3S,4S,5R)-3,4-dihydroxy(tetrahydrofuran-2,5-diyl)bis(methylene) dibenzoate (86363-73-7) → 3-O-(2-O-acetyl-α-L-idopyranosyl)-2,5-anhydro-1,6-di-O-benzoyl-D-mannitol (735327-12-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 81 percent / TfOH; NIS; molecular sieve / CH₂Cl₂ / -40 - 20 °C

2: 95 percent / hydrogen / Pd/C / H₂O; methanol / 6 h / 20 °C

With N-iodo-succinimide; molecular sieve; trifluorormethanesulfonic acid; hydrogen; palladium on activated charcoal; In methanol; dichloromethane; water;

DOI:10.1016/j.carres.2004.03.006

upstream raw materials:

3-O-(2-O-acetyl-3-O-benzyl-4,6-O-benzylidene-α-L-idopyranosyl)-2,5-anhydro-1,6-di-O-benzoyl-D-mannitol

benzoyl chloride

(2R,3S,4S,5R)-3,4-dihydroxy(tetrahydrofuran-2,5-diyl)bis(methylene) dibenzoate

phenyl 3-O-benzyl-1-thio-α-L-idopyranoside

Downstream raw materials:

C₃₄H₄₆O₁₃Si

3-O-(2-O-acetyl-3,4-di-O-benzoyl-α-L-idopyranosyl)-2,5-anhydro-1,4,6-tri-O-benzoyl-D-mannitol

2,5-anhydro-1,4,6-tri-O-benzoyl-3-O-(2-O-acetyl-3,4-di-O-benzoyl-α-L-idopyranosyluronic acid)-D-mannitol

3-O-(2-O-acetyl-3,4-di-O-benzoyl-6-O-t-butyldimethylsilyl-α-L-idopyranosyl)-2,5-anhydro-1,4,6-tri-O-benzoyl-D-mannitol