Toluene-4-sulfonic acid (R)-2-((2R,3R,4S,5S)-4-azido-3-benzyloxy-5-methoxy-tetrahydro-furan-2-yl)-2-hydroxy-ethyl ester

Base Information

• Chemical Name: Toluene-4-sulfonic acid (R)-2-((2R,3R,4S,5S)-4-azido-3-benzyloxy-5-methoxy-tetrahydro-furan-2-yl)-2-hydroxy-ethyl ester
• CAS No.: 98260-59-4
• Molecular Formula: C₂₁H₂₅N₃O₇S
• Molecular Weight: 463.511
• Mol file: 98260-59-4.mol

Synonyms:Toluene-4-sulfonic acid (R)-2-((2R,3R,4S,5S)-4-azido-3-benzyloxy-5-methoxy-tetrahydro-furan-2-yl)-2-hydroxy-ethyl ester

Chemical Property of Toluene-4-sulfonic acid (R)-2-((2R,3R,4S,5S)-4-azido-3-benzyloxy-5-methoxy-tetrahydro-furan-2-yl)-2-hydroxy-ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Toluene-4-sulfonic acid (R)-2-((2R,3R,4S,5S)-4-azido-3-benzyloxy-5-methoxy-tetrahydro-furan-2-yl)-2-hydroxy-ethyl ester

There total 8 articles about Toluene-4-sulfonic acid (R)-2-((2R,3R,4S,5S)-4-azido-3-benzyloxy-5-methoxy-tetrahydro-furan-2-yl)-2-hydroxy-ethyl ester 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:

3-O-benzyl-1,2-O-isopropylidene-α-D-glucofuranose-5,6-carbonate (16895-86-6) → Toluene-4-sulfonic acid (R)-2-((2R,3R,4S,5S)-4-azido-3-benzyloxy-5-methoxy-tetrahydro-furan-2-yl)-2-hydroxy-ethyl ester (98260-59-4)

Guidance literature:

Multi-step reaction with 5 steps

1: methanol / Dowex 50W-X₈ resin (H⁺ form) / Heating

2: pyridine / CH₂Cl₂ / 0.33 h / -20 °C

3: NaN₃ / dimethylformamide / 48 h / 50 °C

4: methanol / sodium methylate / Ambient temperature

5: pyridine / 6 h / Ambient temperature

With pyridine; methanol; sodium azide; Dowex 50W-X₈ resin (H⁺ form); sodium methylate; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(00)99073-7

Reference yield:

methyl-3-O-benzyl-α-D-glucofuranoside-5,6-carbonate (16895-87-7) → Toluene-4-sulfonic acid (R)-2-((2R,3R,4S,5S)-4-azido-3-benzyloxy-5-methoxy-tetrahydro-furan-2-yl)-2-hydroxy-ethyl ester (98260-59-4)

Guidance literature:

Multi-step reaction with 4 steps

1: pyridine / CH₂Cl₂ / 0.33 h / -20 °C

2: NaN₃ / dimethylformamide / 48 h / 50 °C

3: methanol / sodium methylate / Ambient temperature

4: pyridine / 6 h / Ambient temperature

With pyridine; methanol; sodium azide; sodium methylate; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(00)99073-7

Reference yield:

(1R)-1-((3aR,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro(2,3-d)(1,3)dioxol-5-yl)ethane-1,2-diol (22529-61-9) → Toluene-4-sulfonic acid (R)-2-((2R,3R,4S,5S)-4-azido-3-benzyloxy-5-methoxy-tetrahydro-furan-2-yl)-2-hydroxy-ethyl ester (98260-59-4)

Guidance literature:

Multi-step reaction with 6 steps

1: sodium methoxide / Heating

2: methanol / Dowex 50W-X₈ resin (H⁺ form) / Heating

3: pyridine / CH₂Cl₂ / 0.33 h / -20 °C

4: NaN₃ / dimethylformamide / 48 h / 50 °C

5: methanol / sodium methylate / Ambient temperature

6: pyridine / 6 h / Ambient temperature

With pyridine; methanol; sodium azide; sodium methylate; Dowex 50W-X₈ resin (H⁺ form); sodium methylate; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(00)99073-7

upstream raw materials:

methyl 2-azido-3-O-benzyl-2-deoxy-α-D-mannofuranoside

p-toluenesulfonyl chloride

3-O-benzyl-1,2-O-isopropylidene-α-D-glucofuranose-5,6-carbonate

methyl-3-O-benzyl-α-D-glucofuranoside-5,6-carbonate

Downstream raw materials:

N-benzyloxycarbonyl-4-O-benzyl-1,5-dideoxy-1,5-imino-D-mannitol

(2S,3R,4R)-3-Benzyloxy-2-formyl-4-hydroxy-piperidine-1-carboxylic acid benzyl ester

D-fagomine

4-O-benzyl-N-benzyloxycarbonyl-1,5-imino-1,2,5-trideoxy-D-arabino-hexitol