(2S,3S,4R,5R)-3-Azido-5-methoxy-4-(toluene-4-sulfonyloxy)-tetrahydro-furan-2-carboxylic acid

Base Information

Chemical Name:(2S,3S,4R,5R)-3-Azido-5-methoxy-4-(toluene-4-sulfonyloxy)-tetrahydro-furan-2-carboxylic acid
CAS No.:175655-97-7
Molecular Formula:C₁₃H₁₅N₃O₇S
Molecular Weight:357.344
Hs Code.:

Synonyms:(2S,3S,4R,5R)-3-Azido-5-methoxy-4-(toluene-4-sulfonyloxy)-tetrahydro-furan-2-carboxylic acid

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Chemical Property of (2S,3S,4R,5R)-3-Azido-5-methoxy-4-(toluene-4-sulfonyloxy)-tetrahydro-furan-2-carboxylic acid

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Technology Process of (2S,3S,4R,5R)-3-Azido-5-methoxy-4-(toluene-4-sulfonyloxy)-tetrahydro-furan-2-carboxylic acid

There total 5 articles about (2S,3S,4R,5R)-3-Azido-5-methoxy-4-(toluene-4-sulfonyloxy)-tetrahydro-furan-2-carboxylic acid 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: 91.0%

: 175655-96-6
methyl 3-azido-3-deoxy-2-O-(p-tolylsulfonyl)-β-D-xylofuranoside

: 175655-97-7
(2S,3S,4R,5R)-3-Azido-5-methoxy-4-(toluene-4-sulfonyloxy)-tetrahydro-furan-2-carboxylic acid

Guidance literature:: With ruthenium trichloride; sodium periodate; In tetrachloromethane; water; acetonitrile; for 4.5h; Ambient temperature;
DOI:10.1021/jo951983z

Reference yield:

: 50908-04-8
(-)-Methyl-5-O-trityl-β-D-ribofuranosid

: 175655-97-7
(2S,3S,4R,5R)-3-Azido-5-methoxy-4-(toluene-4-sulfonyloxy)-tetrahydro-furan-2-carboxylic acid

Guidance literature:: Multi-step reaction with 5 steps

1: 86 percent / triethylamine, thionyl chloride / tetrahydrofuran / 0.75 h / -25 °C

2: 80 percent / sodium azide / hexamethylphosphoric acid triamide / 15 h / 100 °C

3: 90 percent / pyridine / 72 h / Ambient temperature

4: 85 percent / sulfuric acid / dioxane / 1.5 h / 100 °C

5: 91 percent / ruthenium trichloride hydrate, sodium metaperiodate / H₂O; CCl₄; acetonitrile / 4.5 h / Ambient temperature

With pyridine; ruthenium trichloride; sodium periodate; thionyl chloride; sodium azide; sulfuric acid; triethylamine; In tetrahydrofuran; 1,4-dioxane; tetrachloromethane; N,N,N,N,N,N-hexamethylphosphoric triamide; water; acetonitrile;
DOI:10.1021/jo951983z

Reference yield:

: 175655-94-4
methyl 3-azido-3-deoxy-5-O-triphenylmethyl-β-D-xylofuranoside

: 175655-97-7
(2S,3S,4R,5R)-3-Azido-5-methoxy-4-(toluene-4-sulfonyloxy)-tetrahydro-furan-2-carboxylic acid

Guidance literature:: Multi-step reaction with 3 steps

1: 90 percent / pyridine / 72 h / Ambient temperature

2: 85 percent / sulfuric acid / dioxane / 1.5 h / 100 °C

3: 91 percent / ruthenium trichloride hydrate, sodium metaperiodate / H₂O; CCl₄; acetonitrile / 4.5 h / Ambient temperature

With pyridine; ruthenium trichloride; sodium periodate; sulfuric acid; In 1,4-dioxane; tetrachloromethane; water; acetonitrile;
DOI:10.1021/jo951983z