Toluene-4-sulfonic acid (2S,3S,4R,5S)-4-azido-5-(diethoxy-phosphorylmethyl)-2-ethoxy-tetrahydro-furan-3-yl ester

Base Information

Chemical Name:Toluene-4-sulfonic acid (2S,3S,4R,5S)-4-azido-5-(diethoxy-phosphorylmethyl)-2-ethoxy-tetrahydro-furan-3-yl ester
CAS No.:191083-76-8
Molecular Formula:C₁₈H₂₈N₃O₈PS
Molecular Weight:477.475
Hs Code.:

Synonyms:Toluene-4-sulfonic acid (2S,3S,4R,5S)-4-azido-5-(diethoxy-phosphorylmethyl)-2-ethoxy-tetrahydro-furan-3-yl ester

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Chemical Property of Toluene-4-sulfonic acid (2S,3S,4R,5S)-4-azido-5-(diethoxy-phosphorylmethyl)-2-ethoxy-tetrahydro-furan-3-yl ester

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Technology Process of Toluene-4-sulfonic acid (2S,3S,4R,5S)-4-azido-5-(diethoxy-phosphorylmethyl)-2-ethoxy-tetrahydro-furan-3-yl ester

There total 11 articles about Toluene-4-sulfonic acid (2S,3S,4R,5S)-4-azido-5-(diethoxy-phosphorylmethyl)-2-ethoxy-tetrahydro-furan-3-yl 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: 95.0%

: 98-59-9
p-toluenesulfonyl chloride

: 191083-75-7
((2S,3S,4S,5S)-3-Azido-5-ethoxy-4-hydroxy-tetrahydro-furan-2-ylmethyl)-phosphonic acid diethyl ester

: 191083-76-8
Toluene-4-sulfonic acid (2S,3S,4R,5S)-4-azido-5-(diethoxy-phosphorylmethyl)-2-ethoxy-tetrahydro-furan-3-yl ester

Guidance literature:: With pyridine; at 20 ℃; for 90h;
DOI:10.1021/jo9623494

Reference yield:

: 63087-96-7
methyl 5-deoxy-5-iodo-2,3-O-isopropylidene-α-D-lyxofuranoside

: 191083-76-8
Toluene-4-sulfonic acid (2S,3S,4R,5S)-4-azido-5-(diethoxy-phosphorylmethyl)-2-ethoxy-tetrahydro-furan-3-yl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 82 percent / 160 °C

2: Heating

3: triethylamine, thionyl chloride / tetrahydrofuran / 0.25 h / -25 °C

4: 2.70 g / ruthenium trichloride hydrate, sodium metaperiodate / acetonitrile; CCl₄; H₂O / 2.5 h / Ambient temperature

5: 1.) sodium azide, 2.) sulfuric acid / 1.) DMF, 60 deg C, 2.5 h, 2.) THF, water, room temperature, 2 h

6: 95 percent / pyridine / 90 h / 20 °C

With pyridine; ruthenium trichloride; sodium periodate; thionyl chloride; sodium azide; sulfuric acid; triethylamine; In tetrahydrofuran; tetrachloromethane; water; acetonitrile;
DOI:10.1021/jo9623494

Reference yield:

: 63029-07-2,828937-29-7
methyl 2,3-O-isopropylidene-α-D-lyxofuranoside

: 191083-76-8
Toluene-4-sulfonic acid (2S,3S,4R,5S)-4-azido-5-(diethoxy-phosphorylmethyl)-2-ethoxy-tetrahydro-furan-3-yl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 75 percent / iodine, triphenylphosphine, imidazole / toluene / 1.5 h / 80 °C

2: 82 percent / 160 °C

3: Heating

4: triethylamine, thionyl chloride / tetrahydrofuran / 0.25 h / -25 °C

5: 2.70 g / ruthenium trichloride hydrate, sodium metaperiodate / acetonitrile; CCl₄; H₂O / 2.5 h / Ambient temperature

6: 1.) sodium azide, 2.) sulfuric acid / 1.) DMF, 60 deg C, 2.5 h, 2.) THF, water, room temperature, 2 h

7: 95 percent / pyridine / 90 h / 20 °C

With pyridine; 1H-imidazole; ruthenium trichloride; sodium periodate; thionyl chloride; sodium azide; sulfuric acid; iodine; triethylamine; triphenylphosphine; In tetrahydrofuran; tetrachloromethane; water; toluene; acetonitrile;
DOI:10.1021/jo9623494