1,2-O-isopropylidene-4-(S)-C-(hydroxymethyl)-5-O-p-toluenesulfonyl-β-L-threo-pento-1,4-furanose

Base Information

• Chemical Name: 1,2-O-isopropylidene-4-(S)-C-(hydroxymethyl)-5-O-p-toluenesulfonyl-β-L-threo-pento-1,4-furanose
• CAS No.: 854921-17-8
• Molecular Formula: C₁₆H₂₂O₈S
• Molecular Weight: 374.412
• Mol file: 854921-17-8.mol

Synonyms:1,2-O-isopropylidene-4-(S)-C-(hydroxymethyl)-5-O-p-toluenesulfonyl-β-L-threo-pento-1,4-furanose

Chemical Property of 1,2-O-isopropylidene-4-(S)-C-(hydroxymethyl)-5-O-p-toluenesulfonyl-β-L-threo-pento-1,4-furanose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1,2-O-isopropylidene-4-(S)-C-(hydroxymethyl)-5-O-p-toluenesulfonyl-β-L-threo-pento-1,4-furanose

There total 1 articles about 1,2-O-isopropylidene-4-(S)-C-(hydroxymethyl)-5-O-p-toluenesulfonyl-β-L-threo-pento-1,4-furanose 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: 57.0%

1,2-O-isopropylidene-4-C-(hydroxymethyl)-β-L-threo-pento-1,4-furanose (55797-64-3,55797-65-4) + p-toluenesulfonyl chloride (98-59-9) → 1,2-O-isopropylidene-4-(S)-C-(hydroxymethyl)-5-O-p-toluenesulfonyl-β-L-threo-pento-1,4-furanose (854921-17-8)

Guidance literature:

With pyridine; at -15 ℃; for 24h;

DOI:10.1039/b418283a

Reference yield:

1,2-O-isopropylidene-4-(S)-C-(hydroxymethyl)-5-O-p-toluenesulfonyl-β-L-threo-pento-1,4-furanose (854921-17-8) → 1,2-O-isopropylidene-4-(S)-C-(hydroxymethyl)-5-(N-benzoxycarbonylamino)-β-L-threo-pento-1,4-furanose (854921-23-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 30 percent / NaN₃; molecular sieves / dimethylformamide / 60 h / 110 °C

2: LiAlH₄ / tetrahydrofuran / 1.5 h / 20 °C

3: 0.598 g / aq. NaHCO₃ / ethanol / 4 h / 20 °C

With lithium aluminium tetrahydride; sodium azide; molecular sieve; sodium hydrogencarbonate; In tetrahydrofuran; ethanol; N,N-dimethyl-formamide;

DOI:10.1039/b418283a

Reference yield:

1,2-O-isopropylidene-4-(S)-C-(hydroxymethyl)-5-O-p-toluenesulfonyl-β-L-threo-pento-1,4-furanose (854921-17-8) → ((2S,3R,4R,5S)-3,4,5-Trihydroxy-2-hydroxymethyl-tetrahydro-furan-2-ylmethyl)-carbamic acid benzyl ester

Guidance literature:

Multi-step reaction with 4 steps

1: 30 percent / NaN₃; molecular sieves / dimethylformamide / 60 h / 110 °C

2: LiAlH₄ / tetrahydrofuran / 1.5 h / 20 °C

3: 0.598 g / aq. NaHCO₃ / ethanol / 4 h / 20 °C

4: 97 percent / aq. TFA / 3 h / 0 - 25 °C

With lithium aluminium tetrahydride; sodium azide; molecular sieve; sodium hydrogencarbonate; trifluoroacetic acid; In tetrahydrofuran; ethanol; N,N-dimethyl-formamide;

DOI:10.1039/b418283a

upstream raw materials:

1,2-O-isopropylidene-4-C-(hydroxymethyl)-β-L-threo-pento-1,4-furanose

p-toluenesulfonyl chloride

Downstream raw materials:

1,2-O-isopropylidene-4-(R)-C-(methyl)-5-(N-benzoxycarbonylamino)-β-L-threo-pento-1,4-furanose

1,2-O-isopropylidene-4-(S)-C-(hydroxymethyl)-5-(N-benzoxycarbonylamino)-β-L-threo-pento-1,4-furanose