1,2:3,5-di-O-isopropylidene-4-(R)-C-(p-toluenesulfonyloxymethyl)-β-L-threo-pento-1,4-furanose

Base Information

Chemical Name:1,2:3,5-di-O-isopropylidene-4-(R)-C-(p-toluenesulfonyloxymethyl)-β-L-threo-pento-1,4-furanose
CAS No.:123045-04-5
Molecular Formula:C₁₉H₂₆O₈S
Molecular Weight:414.477
Hs Code.:

Synonyms:1,2:3,5-di-O-isopropylidene-4-(R)-C-(p-toluenesulfonyloxymethyl)-β-L-threo-pento-1,4-furanose

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Chemical Property of 1,2:3,5-di-O-isopropylidene-4-(R)-C-(p-toluenesulfonyloxymethyl)-β-L-threo-pento-1,4-furanose

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Technology Process of 1,2:3,5-di-O-isopropylidene-4-(R)-C-(p-toluenesulfonyloxymethyl)-β-L-threo-pento-1,4-furanose

There total 2 articles about 1,2:3,5-di-O-isopropylidene-4-(R)-C-(p-toluenesulfonyloxymethyl)-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: 92.0%

: 123045-02-3
1,2:3,5-di-O-isopropylidene-4-(R)-C-(hydroxymethyl)-β-L-threo-pento-1,4-furanose

: 98-59-9
p-toluenesulfonyl chloride

: 123045-04-5
1,2:3,5-di-O-isopropylidene-4-(R)-C-(p-toluenesulfonyloxymethyl)-β-L-threo-pento-1,4-furanose

Guidance literature:: With pyridine; at 20 ℃; for 12h;
DOI:10.1039/b418283a

Reference yield:

: 55797-64-3,55797-65-4
1,2-O-isopropylidene-4-C-(hydroxymethyl)-β-L-threo-pento-1,4-furanose

: 123045-04-5
1,2:3,5-di-O-isopropylidene-4-(R)-C-(p-toluenesulfonyloxymethyl)-β-L-threo-pento-1,4-furanose

Guidance literature:: Multi-step reaction with 2 steps

1: 97 percent / p-TSA / methanol / 0.08 h / 25 °C

2: 92 percent / pyridine / 12 h / 20 °C

With pyridine; toluene-4-sulfonic acid; In methanol;
DOI:10.1039/b418283a

Reference yield:

: 123045-04-5
1,2:3,5-di-O-isopropylidene-4-(R)-C-(p-toluenesulfonyloxymethyl)-β-L-threo-pento-1,4-furanose

: ((2R,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: 62 percent / NaN₃; TBAI; molecular sieves / dimethylformamide / 48 h / 110 °C

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

3: 0.485 g / aq. NaHCO₃ / ethanol / 4 h / 20 °C

4: 98 percent / aq. TFA / 3 h / 0 - 25 °C

With lithium aluminium tetrahydride; sodium azide; molecular sieve; tetra-(n-butyl)ammonium iodide; sodium hydrogencarbonate; trifluoroacetic acid; In tetrahydrofuran; ethanol; N,N-dimethyl-formamide;
DOI:10.1039/b418283a