(2S,3S,4R,5S)-N-benzyloxycarbonyl-2-tosyloxymethyl-3,4-O-isopropylidene-5-methylpyrrolidine-3,4-diol

Base Information

• Chemical Name: (2S,3S,4R,5S)-N-benzyloxycarbonyl-2-tosyloxymethyl-3,4-O-isopropylidene-5-methylpyrrolidine-3,4-diol
• CAS No.: 1632124-94-7
• Molecular Formula: C₂₄H₂₉NO₇S
• Molecular Weight: 475.563
• Mol file: 1632124-94-7.mol

Synonyms:(2S,3S,4R,5S)-N-benzyloxycarbonyl-2-tosyloxymethyl-3,4-O-isopropylidene-5-methylpyrrolidine-3,4-diol

Chemical Property of (2S,3S,4R,5S)-N-benzyloxycarbonyl-2-tosyloxymethyl-3,4-O-isopropylidene-5-methylpyrrolidine-3,4-diol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S,4R,5S)-N-benzyloxycarbonyl-2-tosyloxymethyl-3,4-O-isopropylidene-5-methylpyrrolidine-3,4-diol

There total 6 articles about (2S,3S,4R,5S)-N-benzyloxycarbonyl-2-tosyloxymethyl-3,4-O-isopropylidene-5-methylpyrrolidine-3,4-diol 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: 73.0%

(2S,3S,4R,5S)-N-benzyloxycarbonyl-2-hydroxymethyl-3,4-O-isopropyliden-5-methylpyrrolidine-3,4-diol (1618698-49-9) + p-toluenesulfonyl chloride (98-59-9) → (2S,3S,4R,5S)-N-benzyloxycarbonyl-2-tosyloxymethyl-3,4-O-isopropylidene-5-methylpyrrolidine-3,4-diol (1632124-94-7)

Guidance literature:

With pyridine; at 0 - 20 ℃; for 4.5h;

DOI:10.3998/ark.5550190.p008.492

Reference yield:

(2S,3S,4R,5S)-2-hydroxymethyl-3,4-O-isopropylidene-5-methylpyrrolidine-3,4-diol (1618698-48-8) → (2S,3S,4R,5S)-N-benzyloxycarbonyl-2-tosyloxymethyl-3,4-O-isopropylidene-5-methylpyrrolidine-3,4-diol (1632124-94-7)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium hydrogencarbonate / ethanol; water / 2 h / 20 °C

2: pyridine / 0 - 20 °C

With pyridine; sodium hydrogencarbonate; In ethanol; water;

DOI:10.1039/c4ob00931b

Reference yield:

(3aS,6R,6aS)-6-((tert-butyldiphenylsilyloxy)methyl)-2,2-dimethyl-tetrahydrofuro[3,4-d]-[1,3]dioxol-4-ol → (2S,3S,4R,5S)-N-benzyloxycarbonyl-2-tosyloxymethyl-3,4-O-isopropylidene-5-methylpyrrolidine-3,4-diol (1632124-94-7)

Guidance literature:

Multi-step reaction with 7 steps

1: sodium hydrogencarbonate; hydroxylamine hydrochloride / ethanol; water / 72 h / 20 °C

2: pyridine / water / 6 h / 0 - 20 °C

3: toluene / 7 h / 70 °C

4: tetrabutyl ammonium fluoride / tetrahydrofuran / 3 h / 20 °C

5: hydrogen; palladium 10% on activated carbon / methanol / 24 h / 10343.2 Torr

6: sodium hydrogencarbonate / ethanol; water / 2 h / 20 °C

7: pyridine / 0 - 20 °C

With pyridine; palladium 10% on activated carbon; hydroxylamine hydrochloride; tetrabutyl ammonium fluoride; hydrogen; sodium hydrogencarbonate; In tetrahydrofuran; methanol; ethanol; water; toluene;

DOI:10.1039/c4ob00931b

upstream raw materials:

(2S,3S,4R,5S)-N-benzyloxycarbonyl-2-hydroxymethyl-3,4-O-isopropyliden-5-methylpyrrolidine-3,4-diol

p-toluenesulfonyl chloride

(2S,3S,4R,5S)-1-benzyloxycarbonyl-2-formyl-5-methylpyrrolidine-3,4-diol

(2S,3S,4R,5S)-2-hydroxymethyl-3,4-O-isopropylidene-5-methylpyrrolidine-3,4-diol

Downstream raw materials:

(2S,3S,4R,5S)-N-benzyloxycarbonyl-2-azidomethyl-3,4-O-isopropylidene-5-methylpyrrolidine-3,4-diol

(2S,3R,4S,5S)-2-methyl-5-[(4-phenyl-1H-1,2,3-triazol-1-yl)methyl]pyrrolidine-3,4-diol

C₂₅H₂₈N₄O₄