(3S,4R)-3-Hydroxy-4-(4-m-tolyloxy-benzenesulfonyl)-tetrahydro-pyran-3-carboxylic acid

Base Information

Chemical Name:(3S,4R)-3-Hydroxy-4-(4-m-tolyloxy-benzenesulfonyl)-tetrahydro-pyran-3-carboxylic acid
CAS No.:756533-78-5
Molecular Formula:C₁₉H₂₀O₇S
Molecular Weight:392.43
Hs Code.:

Synonyms:(3S,4R)-3-Hydroxy-4-(4-m-tolyloxy-benzenesulfonyl)-tetrahydro-pyran-3-carboxylic acid

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Chemical Property of (3S,4R)-3-Hydroxy-4-(4-m-tolyloxy-benzenesulfonyl)-tetrahydro-pyran-3-carboxylic acid

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Technology Process of (3S,4R)-3-Hydroxy-4-(4-m-tolyloxy-benzenesulfonyl)-tetrahydro-pyran-3-carboxylic acid

There total 8 articles about (3S,4R)-3-Hydroxy-4-(4-m-tolyloxy-benzenesulfonyl)-tetrahydro-pyran-3-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: 80.0%

: 756533-55-8
(3R,4R)-3-Hydroxymethyl-4-(4-m-tolyloxy-benzenesulfonyl)-tetrahydro-pyran-3-ol

: 756533-78-5
(3S,4R)-3-Hydroxy-4-(4-m-tolyloxy-benzenesulfonyl)-tetrahydro-pyran-3-carboxylic acid

Guidance literature:: With 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; sodium chlorite; In acetonitrile; pH=7.0;
DOI:10.1016/j.bmcl.2004.06.081

Reference yield:

: 14774-35-7
(S)-tetrahydropyran-3-yl-carboxaldehyde

: 756533-78-5
(3S,4R)-3-Hydroxy-4-(4-m-tolyloxy-benzenesulfonyl)-tetrahydro-pyran-3-carboxylic acid

Guidance literature:: Multi-step reaction with 9 steps

1: 99 percent / Et₃N; DMAP / CH₂Cl₂

2: 90 percent / (DHQ)2PHAL; aq. K₂OsO₄; K₃Fe(CN)6 / K₂CO₃ / 2-methyl-propan-2-ol

3: SOCl₂; Et₃N / CH₂Cl₂

4: RuCl₃; aq. NaIO₄ / CCl₄; acetonitrile

5: 93 percent / NaH / dimethylformamide / Heating

6: 74 percent / CH₃CO₃H; NaOAc / CH₂Cl₂

7: Cu(OAc)2; Et₃N; O₂ / CH₂Cl₂ / 24 h / 20 °C

8: K₂CO₃ / methanol / 20 °C

9: 80 percent / aq. NaOCl; NaClO₂; TEMPO / acetonitrile / pH 7.0

With peracetic acid; dmap; ruthenium trichloride; 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; sodium chlorite; potassium osmate(VI); sodium periodate; thionyl chloride; copper diacetate; Hydroquinone 1,4-phthalazinediyl diether; oxygen; sodium acetate; sodium hydride; potassium carbonate; triethylamine; potassium hexacyanoferrate(III); potassium carbonate; In methanol; tetrachloromethane; dichloromethane; N,N-dimethyl-formamide; acetonitrile; tert-butyl alcohol;
DOI:10.1016/j.bmcl.2004.06.081

Reference yield:

: 756533-15-0
4-methoxy-benzoic acid 5,6-dihydro-2H-pyran-3-ylmethyl ester

: 756533-78-5
(3S,4R)-3-Hydroxy-4-(4-m-tolyloxy-benzenesulfonyl)-tetrahydro-pyran-3-carboxylic acid

Guidance literature:: Multi-step reaction with 8 steps

1: 90 percent / (DHQ)2PHAL; aq. K₂OsO₄; K₃Fe(CN)6 / K₂CO₃ / 2-methyl-propan-2-ol

2: SOCl₂; Et₃N / CH₂Cl₂

3: RuCl₃; aq. NaIO₄ / CCl₄; acetonitrile

4: 93 percent / NaH / dimethylformamide / Heating

5: 74 percent / CH₃CO₃H; NaOAc / CH₂Cl₂

6: Cu(OAc)2; Et₃N; O₂ / CH₂Cl₂ / 24 h / 20 °C

7: K₂CO₃ / methanol / 20 °C

8: 80 percent / aq. NaOCl; NaClO₂; TEMPO / acetonitrile / pH 7.0

With peracetic acid; ruthenium trichloride; 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; sodium chlorite; potassium osmate(VI); sodium periodate; thionyl chloride; copper diacetate; Hydroquinone 1,4-phthalazinediyl diether; oxygen; sodium acetate; sodium hydride; potassium carbonate; triethylamine; potassium hexacyanoferrate(III); potassium carbonate; In methanol; tetrachloromethane; dichloromethane; N,N-dimethyl-formamide; acetonitrile; tert-butyl alcohol;
DOI:10.1016/j.bmcl.2004.06.081