4-O-acetyl-1,5-anhydro-2-O-benzoyl-3-oxo-L-arabino-pentitol (p-tolylsulfonyl)hydrazone

Base Information

Chemical Name:4-O-acetyl-1,5-anhydro-2-O-benzoyl-3-oxo-L-arabino-pentitol (p-tolylsulfonyl)hydrazone
CAS No.:122948-65-6
Molecular Formula:C₂₁H₂₂N₂O₇S
Molecular Weight:446.481
Hs Code.:

Synonyms:4-O-acetyl-1,5-anhydro-2-O-benzoyl-3-oxo-L-arabino-pentitol (p-tolylsulfonyl)hydrazone

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Chemical Property of 4-O-acetyl-1,5-anhydro-2-O-benzoyl-3-oxo-L-arabino-pentitol (p-tolylsulfonyl)hydrazone

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Technology Process of 4-O-acetyl-1,5-anhydro-2-O-benzoyl-3-oxo-L-arabino-pentitol (p-tolylsulfonyl)hydrazone

There total 19 articles about 4-O-acetyl-1,5-anhydro-2-O-benzoyl-3-oxo-L-arabino-pentitol (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: 96.0%

: 122948-64-5
4-O-acetyl-1,5-anhydro-2-O-benzoyl-3-deoxy-3-<2-(p-tolylsulfonyl)hydrazino>-L-lyxo-pentitol

: 122948-65-6
4-O-acetyl-1,5-anhydro-2-O-benzoyl-3-oxo-L-arabino-pentitol (p-tolylsulfonyl)hydrazone

Guidance literature:: With 4-methyl-morpholine; N-iodo-succinimide; In chloroform; at 0 ℃;
DOI:10.1021/jo00283a047

Reference yield:

: 87-72-9,608-45-7,608-46-8,608-47-9,2460-44-8,6748-95-4,6763-34-4,7261-26-9,7283-06-9,7283-07-0,7296-55-1,7296-56-2,7296-58-4,7296-59-5,7296-60-8,7296-61-9,7296-62-0,7322-30-7,10257-31-5,10257-32-6,10257-33-7,10257-34-8,10257-35-9,19982-83-3,20242-88-0,28697-53-2,36562-42-2,41546-41-2,89299-64-9,107655-34-5,115794-06-4,115794-07-5,130550-15-1,130606-21-2
L-(+)-arabinose

: 122948-65-6,123164-76-1,123164-77-2
4-O-acetyl-1,5-anhydro-2-O-benzoyl-3-oxo-L-arabino-pentitol anti-(p-tolylsulfonyl)hydrazone

Guidance literature:: Multi-step reaction with 9 steps

1: pyridine / Ambient temperature

2: phosphorus tribromide / acetic acid / 4 h / Ambient temperature

3: 1.) AIBN, tributyltin hydride, 2.) aq. KF / 1.) dietyl ether, RT, 5 h, 2.) 0.5 h

4: NaOMe / methanol

5: p-toluenesulfonic acid / CH₂Cl₂ / Ambient temperature

6: NEt₃, DMAP / CH₂Cl₂ / Ambient temperature

7: 80 percent aq.acetic acid / 0.5 h / Ambient temperature

8: 80 percent / pyridinum chlorochromate, sodium acetate, mol. sieves 3-A / CH₂Cl₂ / 3 h / Ambient temperature

9: ethanol / Heating

With pyridine; dmap; potassium fluoride; 2,2'-azobis(isobutyronitrile); 3 A molecular sieve; tri-n-butyl-tin hydride; sodium methylate; sodium acetate; phosphorus tribromide; toluene-4-sulfonic acid; acetic acid; triethylamine; pyridinium chlorochromate; In methanol; ethanol; dichloromethane; acetic acid;
DOI:10.1021/jo00278a035

Reference yield:

: 87-72-9,608-45-7,608-46-8,608-47-9,2460-44-8,6748-95-4,6763-34-4,7261-26-9,7283-06-9,7283-07-0,7296-55-1,7296-56-2,7296-58-4,7296-59-5,7296-60-8,7296-61-9,7296-62-0,7322-30-7,10257-31-5,10257-32-6,10257-33-7,10257-34-8,10257-35-9,19982-83-3,20242-88-0,28697-53-2,36562-42-2,41546-41-2,89299-64-9,107655-34-5,115794-06-4,115794-07-5,130550-15-1,130606-21-2
L-(+)-arabinose

: 122948-65-6,123164-76-1,123164-77-2
4-O-acetyl-1,5-anhydro-2-O-benzoyl-3-oxo-L-arabino-pentitol syn-(p-tolylsulfonyl)hydrazone

Guidance literature:: Multi-step reaction with 9 steps

1: pyridine / Ambient temperature

2: phosphorus tribromide / acetic acid / 4 h / Ambient temperature

3: 1.) AIBN, tributyltin hydride, 2.) aq. KF / 1.) dietyl ether, RT, 5 h, 2.) 0.5 h

4: NaOMe / methanol

5: p-toluenesulfonic acid / CH₂Cl₂ / Ambient temperature

6: NEt₃, DMAP / CH₂Cl₂ / Ambient temperature

7: 80 percent aq.acetic acid / 0.5 h / Ambient temperature

8: 80 percent / pyridinum chlorochromate, sodium acetate, mol. sieves 3-A / CH₂Cl₂ / 3 h / Ambient temperature

9: ethanol / Heating

With pyridine; dmap; potassium fluoride; 2,2'-azobis(isobutyronitrile); 3 A molecular sieve; tri-n-butyl-tin hydride; sodium methylate; sodium acetate; phosphorus tribromide; toluene-4-sulfonic acid; acetic acid; triethylamine; pyridinium chlorochromate; In methanol; ethanol; dichloromethane; acetic acid;
DOI:10.1021/jo00278a035