methyl 4-O-acetyl-2-O-benzoyl-6-deoxy-β-L-xylo-hexopyranosid-3-ulose (p-tolylsulfonyl)hydrazone

Base Information

• Chemical Name: methyl 4-O-acetyl-2-O-benzoyl-6-deoxy-β-L-xylo-hexopyranosid-3-ulose (p-tolylsulfonyl)hydrazone
• CAS No.: 123098-97-5
• Molecular Formula: C₂₃H₂₆N₂O₈S
• Molecular Weight: 490.534
• Mol file: 123098-97-5.mol

Synonyms:

Chemical Property of methyl 4-O-acetyl-2-O-benzoyl-6-deoxy-β-L-xylo-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-acetyl-2-O-benzoyl-6-deoxy-β-L-xylo-hexopyranosid-3-ulose (p-tolylsulfonyl)hydrazone

There total 6 articles about methyl 4-O-acetyl-2-O-benzoyl-6-deoxy-β-L-xylo-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: 74.0%

methyl 4-O-acetyl-2-O-benzoyl-6-deoxy-β-L-xylo-hexopyranosid-3-ulose (123076-99-3) + toluene-4-sulfonic acid hydrazide (1576-35-8) → methyl 4-O-acetyl-2-O-benzoyl-6-deoxy-β-L-xylo-hexopyranosid-3-ulose (p-tolylsulfonyl)hydrazone (123098-97-5)

Guidance literature:

In ethanol; Heating;

DOI:10.1021/jo00278a035

Reference yield:

(3S,4R,5S,6S)-2-methoxy-6-methyltetrahydro-2H-pyran-3,4,5-triol (65310-00-1) → methyl 4-O-acetyl-2-O-benzoyl-6-deoxy-β-L-xylo-hexopyranosid-3-ulose (p-tolylsulfonyl)hydrazone (123098-97-5)

Guidance literature:

Multi-step reaction with 5 steps

1: p-toluenosulfonic acid / CH₂Cl₂ / Ambient temperature

2: triethyl amine, 4-(dimethylamino)pyririne / CH₂Cl₂ / Heating

3: 80 percent aq. acetic acid / 0.5 h / Ambient temperature

4: 89 percent / pyridinum chlorochromate, sodium acetate, molec. sievesA-3 / CH₂Cl₂; diethyl ether / 3 h / 0 - 20 °C

5: 74 percent / ethanol / Heating

With dmap; 3 A molecular sieve; sodium acetate; toluene-4-sulfonic acid; acetic acid; triethylamine; pyridinium chlorochromate; In diethyl ether; ethanol; dichloromethane;

DOI:10.1021/jo00278a035

Reference yield:

methyl 6-deoxy-3,4-O-(1-ethoxyetylidene)-β-L-galactopyranoside (123076-95-9) → methyl 4-O-acetyl-2-O-benzoyl-6-deoxy-β-L-xylo-hexopyranosid-3-ulose (p-tolylsulfonyl)hydrazone (123098-97-5)

Guidance literature:

Multi-step reaction with 4 steps

1: triethyl amine, 4-(dimethylamino)pyririne / CH₂Cl₂ / Heating

2: 80 percent aq. acetic acid / 0.5 h / Ambient temperature

3: 89 percent / pyridinum chlorochromate, sodium acetate, molec. sievesA-3 / CH₂Cl₂; diethyl ether / 3 h / 0 - 20 °C

4: 74 percent / ethanol / Heating

With dmap; 3 A molecular sieve; sodium acetate; acetic acid; triethylamine; pyridinium chlorochromate; In diethyl ether; ethanol; dichloromethane;

DOI:10.1021/jo00278a035

upstream raw materials:

methyl 4-O-acetyl-2-O-benzoyl-6-deoxy-β-L-xylo-hexopyranosid-3-ulose

toluene-4-sulfonic acid hydrazide

(3S,4R,5S,6S)-2-methoxy-6-methyltetrahydro-2H-pyran-3,4,5-triol

methyl 6-deoxy-3,4-O-(1-ethoxyetylidene)-β-L-galactopyranoside

Downstream raw materials:

methyl 4-O-acetyl-2-O-benzoyl-3,6-dideoxy-3-<2-(p-tolylsulfonyl)hydrazino>-β-L-galactopyranoside

methyl 4-O-acetyl-2-O-benzoyl-3,6-dideoxy-3-<2-(p-tolylsulfonyl)hydrazino>-β-L-gulopyranoside