methyl 4-O-benzyl-2,6-dideoxy-β-L-threo-hexopyranosid-3-ulose

Base Information

• Chemical Name: methyl 4-O-benzyl-2,6-dideoxy-β-L-threo-hexopyranosid-3-ulose
• CAS No.: 93978-83-7
• Molecular Formula: C₁₄H₁₆O₅
• Molecular Weight: 264.278
• Mol file: 93978-83-7.mol

Synonyms:methyl 4-O-benzyl-2,6-dideoxy-β-L-threo-hexopyranosid-3-ulose

Chemical Property of methyl 4-O-benzyl-2,6-dideoxy-β-L-threo-hexopyranosid-3-ulose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 4-O-benzyl-2,6-dideoxy-β-L-threo-hexopyranosid-3-ulose

There total 7 articles about methyl 4-O-benzyl-2,6-dideoxy-β-L-threo-hexopyranosid-3-ulose 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: 90.8%

methyl 4-O-benzoyl-2,6-dideoxy-β-L-lyxo-hexopyranoside (93960-59-9) → methyl 4-O-benzyl-2,6-dideoxy-β-L-threo-hexopyranosid-3-ulose (93978-83-7)

Guidance literature:

With pyridinium chlorochromate; In dichloromethane; Heating; molecular sieves 3A, overnight;

DOI:10.1246/bcsj.57.2538

Reference yield:

methyl 4-O-benzoyl-6-bromo-2,6-dideoxy-α-D-ribo-hexopyranoside (83497-33-0) → methyl 4-O-benzyl-2,6-dideoxy-β-L-threo-hexopyranosid-3-ulose (93978-83-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 92.2 percent / Ag₂O / dimethylformamide / 24 h

2: 1) AgF, 2) H₂ / 2) 10percent Pd/C / 1) pyridine, 40 h, 2) CH₃OH-CH₃CO₂H, overnight

3: 100 percent / Ag₂O / dimethylformamide / 48 h / Ambient temperature

4: 90.8 percent / pyridinium chlorochromate / CH₂Cl₂ / Heating; molecular sieves 3A, overnight

With hydrogen; silver fluoride; pyridinium chlorochromate; silver(l) oxide; palladium on activated charcoal; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1246/bcsj.57.2538

Reference yield:

methyl 3-O-benzoyl-4-O-benzyl-6-bromo-2,6-dideoxy-α-D-ribo-hexopyranoside (93960-55-5) → methyl 4-O-benzyl-2,6-dideoxy-β-L-threo-hexopyranosid-3-ulose (93978-83-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 1) AgF, 2) H₂ / 2) 10percent Pd/C / 1) pyridine, 40 h, 2) CH₃OH-CH₃CO₂H, overnight

2: 100 percent / Ag₂O / dimethylformamide / 48 h / Ambient temperature

3: 90.8 percent / pyridinium chlorochromate / CH₂Cl₂ / Heating; molecular sieves 3A, overnight

With hydrogen; silver fluoride; pyridinium chlorochromate; silver(l) oxide; palladium on activated charcoal; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1246/bcsj.57.2538

upstream raw materials:

methyl 4-O-benzoyl-2,6-dideoxy-β-L-lyxo-hexopyranoside

methyl 2,6-dideoxy-β-L-lyxo-hexopyranoside

benzyl bromide

methyl 4-O-benzoyl-6-bromo-2,6-dideoxy-α-D-ribo-hexopyranoside