(3S,4R,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydro-3-furanyl 4-methylbenzenesulfonate

Base Information

Chemical Name:(3S,4R,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydro-3-furanyl 4-methylbenzenesulfonate
CAS No.:268545-18-2
Molecular Formula:C₁₂H₁₆O₆S
Molecular Weight:288.321
Hs Code.:

Synonyms:(3S,4R,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydro-3-furanyl 4-methylbenzenesulfonate

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (3S,4R,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydro-3-furanyl 4-methylbenzenesulfonate

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Technology Process of (3S,4R,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydro-3-furanyl 4-methylbenzenesulfonate

There total 5 articles about (3S,4R,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydro-3-furanyl 4-methylbenzenesulfonate 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: 75.0%

: 268545-17-1
((2R,3S,4S)-3-hydroxy-4-{[(4-methylphenyl)sulfonyl]oxy}tetrahydro-2-furanyl)methyl benzoate

: 268545-18-2
(3S,4R,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydro-3-furanyl 4-methylbenzenesulfonate

Guidance literature:: With sodium carbonate; In methanol; ethanol; at 20 ℃; for 24h;
DOI:10.1080/15257770008033001

Reference yield:

: 4099-85-8,5531-21-5,20672-63-3,20672-65-5,58763-00-1,63029-07-2,72402-14-3,84894-45-1,129263-68-9,828937-29-7
methyl 2,3-O-isopropylidene-D-ribofuranoside

: 268545-18-2
(3S,4R,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydro-3-furanyl 4-methylbenzenesulfonate

Guidance literature:: Multi-step reaction with 5 steps

1.1: 91 percent / pyridine / 4 h / 20 °C

2.1: Dowex 50 H⁺ resin / methanol / 20 °C

3.1: HMDS; ammonium sulfate / Heating

3.2: 44 percent / triethyl silane; trimethylsilyl triflate / acetonitrile / 1.25 h / 20 °C

4.1: tetrabutylammonium bromide; Bu₂SnO / CH₂Cl₂ / 4.5 h / 20 °C

5.1: 75 percent / sodium carbonate / ethanol; methanol / 24 h / 20 °C

With pyridine; ammonium sulfate; Dowex 50 H⁺ resin; tetrabutylammomium bromide; di(n-butyl)tin oxide; sodium carbonate; 1,1,1,3,3,3-hexamethyl-disilazane; In methanol; ethanol; dichloromethane; 1.1: Acylation / 2.1: Hydrolysis / 3.1: Substitution / 3.2: Elimination / 4.1: Tosylation / 5.1: Hydrolysis;
DOI:10.1080/15257770008033001

Reference yield:

: 156475-03-5
[(2R,3S,4S)-3,4-dihydroxytetrahydro-2-furanyl]methyl benzoate

: 268545-18-2
(3S,4R,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydro-3-furanyl 4-methylbenzenesulfonate

Guidance literature:: Multi-step reaction with 2 steps

1: tetrabutylammonium bromide; Bu₂SnO / CH₂Cl₂ / 4.5 h / 20 °C

2: 75 percent / sodium carbonate / ethanol; methanol / 24 h / 20 °C

With tetrabutylammomium bromide; di(n-butyl)tin oxide; sodium carbonate; In methanol; ethanol; dichloromethane; 1: Tosylation / 2: Hydrolysis;
DOI:10.1080/15257770008033001