methyl 3-O-benzoyl-2,6-dideoxy-α-D-erythro-hexopyranosid-4-ulose

Base Information

• Chemical Name: methyl 3-O-benzoyl-2,6-dideoxy-α-D-erythro-hexopyranosid-4-ulose
• CAS No.: 123077-03-2
• Molecular Formula: C₁₄H₁₆O₅
• Molecular Weight: 264.278
• Mol file: 123077-03-2.mol

Synonyms:methyl 3-O-benzoyl-2,6-dideoxy-α-D-erythro-hexopyranosid-4-ulose

Chemical Property of methyl 3-O-benzoyl-2,6-dideoxy-α-D-erythro-hexopyranosid-4-ulose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 3-O-benzoyl-2,6-dideoxy-α-D-erythro-hexopyranosid-4-ulose

There total 7 articles about methyl 3-O-benzoyl-2,6-dideoxy-α-D-erythro-hexopyranosid-4-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: 92.0%

methyl 3-O-benzoyl-2,6-dideoxy-α-D-ribo-hexopyranoside (104652-05-3) → methyl 3-O-benzoyl-2,6-dideoxy-α-D-erythro-hexopyranosid-4-ulose (123077-03-2)

Guidance literature:

With mol. siev. 3-A; sodium acetate; pyridinium chlorochromate; In dichloromethane; for 2h; Ambient temperature;

DOI:10.1021/jo00278a035

Reference yield:

Benzoic acid (2S,3S,4S,6S)-2-bromomethyl-3-hydroxy-6-methoxy-tetrahydro-pyran-4-yl ester (93960-50-0) → methyl 3-O-benzoyl-2,6-dideoxy-α-D-erythro-hexopyranosid-4-ulose (123077-03-2)

Guidance literature:

Multi-step reaction with 2 steps

1: Bu₃SnH; AIBN / benzene

2: 69 percent / pyridinium chlorochromate / CH₂Cl₂

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; pyridinium chlorochromate; In dichloromethane; benzene;

DOI:10.1002/1521-3773(20010202)40:3<607::AID-ANIE607>3.0.CO;2-8

Reference yield:

methyl 4,6-O-benzylidene-2-deoxy-α-D-altropyranoside (16718-95-9) → methyl 3-O-benzoyl-2,6-dideoxy-α-D-erythro-hexopyranosid-4-ulose (123077-03-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 60 percent / N-bromosuccinimide, barium carbonate / CCl₄ / 0.33 h / 45 °C

2: tributyltin hydride, azobisisobutyronitrile (AIBN) / toluene / 2 h / 60 °C

3: 92 percent / pyridinium chlorochromate, sodium acetate, mol. siev. 3-A / CH₂Cl₂ / 2 h / Ambient temperature

With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); mol. siev. 3-A; tri-n-butyl-tin hydride; sodium acetate; barium carbonate; pyridinium chlorochromate; In tetrachloromethane; dichloromethane; toluene;

DOI:10.1021/jo00278a035

upstream raw materials:

methyl 3-O-benzoyl-2,6-dideoxy-α-D-ribo-hexopyranoside

Benzoic acid (2S,3S,4S,6S)-2-bromomethyl-3-hydroxy-6-methoxy-tetrahydro-pyran-4-yl ester

methyl 4,6-O-benzylidene-2-deoxy-α-D-altropyranoside

methyl 4,6-O-benzylidene-2,3-di-O-p-toluenesulphonyl-α-D-glucopyranoside

Downstream raw materials:

methyl 3-O-benzoyl-2,3,6-trideoxy-4-<2-(p-tolylsulfonyl)hydrazino>-α-D-ribo-hexopyranoside

methyl 3-O-benzoyl-2,6-dideoxy-α-D-erythro-hexopyranosid-4-ulose (p-tolylsulfonyl)hydrazone