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

Base Information

• Chemical Name: methyl 4-O-benzoyl-2,6-dideoxy-α-D-erythro-hexopyranosid-3-ulose (p-tolylsulfonyl)hydrazone
• CAS No.: 123098-98-6
• Molecular Formula: C₂₁H₂₄N₂O₆S
• Molecular Weight: 432.497
• Mol file: 123098-98-6.mol

Synonyms:

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 8 articles about methyl 4-O-benzoyl-2,6-dideoxy-α-D-erythro-hexopyranosid-3-ulose (p-tolylsulfonyl)hydrazone 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: 90.0%

methyl 4-O-benzoyl-2,6-dideoxy-α-D-erythro-hexopyranosyl-3-ulose (123077-02-1) + toluene-4-sulfonic acid hydrazide (1576-35-8) → methyl 4-O-benzoyl-2,6-dideoxy-α-D-erythro-hexopyranosid-3-ulose (p-tolylsulfonyl)hydrazone (123098-98-6)

Guidance literature:

In ethanol; Heating;

DOI:10.1021/jo00278a035

Reference yield:

methyl 4,6-O-benzylidene-α-D-glucopyranoside (3162-96-7) → methyl 4-O-benzoyl-2,6-dideoxy-α-D-erythro-hexopyranosid-3-ulose (p-tolylsulfonyl)hydrazone (123098-98-6)

Guidance literature:

Multi-step reaction with 6 steps

1: 78 percent / pyridine / 48 h / 50 °C

2: 94 percent / lithium triethylborohydride / tetrahydrofuran / 1 h / Heating

3: 60 percent / N-bromosuccinimide, barium carbonate / CCl₄ / 0.33 h / 45 °C

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

5: 95 percent / pyridinium chlorochromate, sodium acetate, mol. siev. 3-A / CH₂Cl₂ / 2 h / Ambient temperature

6: 90 percent / ethanol / Heating

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

DOI:10.1021/jo00278a035

Reference yield:

methyl 4,6-O-benzylidene-2-deoxy-α-D-altropyranoside (16718-95-9) → methyl 4-O-benzoyl-2,6-dideoxy-α-D-erythro-hexopyranosid-3-ulose (p-tolylsulfonyl)hydrazone (123098-98-6)

Guidance literature:

Multi-step reaction with 4 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: 95 percent / pyridinium chlorochromate, sodium acetate, mol. siev. 3-A / CH₂Cl₂ / 2 h / Ambient temperature

4: 90 percent / ethanol / Heating

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

DOI:10.1021/jo00278a035

upstream raw materials:

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

toluene-4-sulfonic acid hydrazide

methyl 4,6-O-benzylidene-α-D-glucopyranoside

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

Downstream raw materials:

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

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