S-2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl [2,3,4,5,6-(2)H5]-phenylthiohydroxamate

Base Information

• Chemical Name: S-2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl [2,3,4,5,6-(2)H5]-phenylthiohydroxamate
• CAS No.: 1034146-60-5
• Molecular Formula: C₂₁H₂₅NO₁₀S
• Molecular Weight: 488.457
• Mol file: 1034146-60-5.mol

Synonyms:S-2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl [2,3,4,5,6-(2)H5]-phenylthiohydroxamate

Chemical Property of S-2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl [2,3,4,5,6-(2)H5]-phenylthiohydroxamate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of S-2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl [2,3,4,5,6-(2)H5]-phenylthiohydroxamate

There total 5 articles about S-2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl [2,3,4,5,6-(2)H5]-phenylthiohydroxamate 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: 60.0%

[2,3,4,5,6-2H5]phenylhydroxamic chloride + tetraacetyl thioglucose (19879-84-6) → S-2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl [2,3,4,5,6-(2)H5]-phenylthiohydroxamate (1034146-60-5)

Guidance literature:

With triethylamine; In diethyl ether; dichloromethane; at 20 ℃; for 2h;

DOI:10.1002/jlcr.1407

Reference yield:

[2,3,4,5,6-2H5]benzaldehyde oxime → S-2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl [2,3,4,5,6-(2)H5]-phenylthiohydroxamate (1034146-60-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / pyridine; N-chlorosuccinimide / CH₂Cl₂ / 2 h / 20 °C

2: 60 percent / triethylamine / diethyl ether; CH₂Cl₂ / 2 h / 20 °C

With pyridine; N-chloro-succinimide; triethylamine; In diethyl ether; dichloromethane;

DOI:10.1002/jlcr.1407

Reference yield:

benzoic acid-2,3,4,5,6-d5 (1079-02-3) → S-2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl [2,3,4,5,6-(2)H5]-phenylthiohydroxamate (1034146-60-5)

Guidance literature:

Multi-step reaction with 5 steps

1: 83 percent / lithium aluminum deuteride / tetrahydrofuran; diethyl ether / 16 h / 40 °C

2: 84 percent / pyridinium chlorochromate / CH₂Cl₂ / 1 h / 20 °C

3: 92 percent / aq. sodium carbonate; hydroxylamine hydrochloride / 2 h / 20 °C

4: 90 percent / pyridine; N-chlorosuccinimide / CH₂Cl₂ / 2 h / 20 °C

5: 60 percent / triethylamine / diethyl ether; CH₂Cl₂ / 2 h / 20 °C

With pyridine; N-chloro-succinimide; lithium aluminium deuteride; hydroxylamine hydrochloride; sodium carbonate; triethylamine; pyridinium chlorochromate; In tetrahydrofuran; diethyl ether; dichloromethane;

DOI:10.1002/jlcr.1407

upstream raw materials:

tetraacetyl thioglucose

2,3,4,5,6-pentadeuteriobenzaldehyde

benzoic acid-2,3,4,5,6-d5

<2,3,4,5,6-D5>-benzyl alcohol