Benzoic acid (2S,3S,4R,5S)-4,5-dihydroxy-2-methoxymethyl-1-(toluene-4-sulfonyl)-piperidin-3-yl ester

Base Information

Chemical Name:Benzoic acid (2S,3S,4R,5S)-4,5-dihydroxy-2-methoxymethyl-1-(toluene-4-sulfonyl)-piperidin-3-yl ester
CAS No.:189152-08-7
Molecular Formula:C₂₁H₂₅NO₇S
Molecular Weight:435.498
Hs Code.:

Synonyms:Benzoic acid (2S,3S,4R,5S)-4,5-dihydroxy-2-methoxymethyl-1-(toluene-4-sulfonyl)-piperidin-3-yl ester

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Chemical Property of Benzoic acid (2S,3S,4R,5S)-4,5-dihydroxy-2-methoxymethyl-1-(toluene-4-sulfonyl)-piperidin-3-yl ester

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Technology Process of Benzoic acid (2S,3S,4R,5S)-4,5-dihydroxy-2-methoxymethyl-1-(toluene-4-sulfonyl)-piperidin-3-yl ester

There total 9 articles about Benzoic acid (2S,3S,4R,5S)-4,5-dihydroxy-2-methoxymethyl-1-(toluene-4-sulfonyl)-piperidin-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: 82.0%

: 189152-02-1
Benzoic acid (3aS,6S,7S,7aR)-6-methoxymethyl-2,2-dioxo-5-(toluene-4-sulfonyl)-hexahydro-1,3-dioxa-2λ⁶-thia-5-aza-inden-7-yl ester

: 189152-08-7
Benzoic acid (2S,3S,4R,5S)-4,5-dihydroxy-2-methoxymethyl-1-(toluene-4-sulfonyl)-piperidin-3-yl ester

Guidance literature:: With sulfuric acid; In tetrahydrofuran; at 40 ℃; for 24h;
DOI:10.1039/a605128f

Reference yield:

: 121564-33-8
N-tosylfurfurylamine

: 189152-08-7
Benzoic acid (2S,3S,4R,5S)-4,5-dihydroxy-2-methoxymethyl-1-(toluene-4-sulfonyl)-piperidin-3-yl ester

Guidance literature:: Multi-step reaction with 9 steps

1: 1.) SnCl₂, LiBr, BuLi / 1.) THF, r.t., 10 min; -78 deg C, 1 h, 2.) -78 deg C, 30 min

2: 89.2 percent / m-CPBA / CH₂Cl₂ / 14 h / Ambient temperature

3: 68.6 percent / BF₃*OEt₂, MS 4A / tetrahydrofuran / 3 h / 0 °C

4: 72.2 percent / CeCl₃*7H₂O, NaBH₄ / methanol / 1 h / -30 °C

5: 86.6 percent / DEAD, PPh₃ / tetrahydrofuran / 3 h / Ambient temperature

6: 83.3 percent / NaBH₄, 88percent formic acid / 1 h / 0 °C

7: 80.9 percent / (DHQ)2-PHAL, OsO₄, K₃Fe(CN)6, K₂CO₃ / 2-methyl-propan-2-ol; H₂O; toluene / 48 h / Ambient temperature

8: 1.) Et₃N, SOCl₂, 2.) RuCl₃*3H₂O, NaIO₄ / 1.) CH₂Cl₂, 0 deg C, 30 min, 2.) CCl₄, CH₃CN, H₂O, 0 deg C, 2 h

9: 82 percent / 50percent aq. H₂SO₄ / tetrahydrofuran / 24 h / 40 °C

With ruthenium trichloride; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; n-butyllithium; formic acid; thionyl chloride; cerium(III) chloride; (DHQ)2-PHAL; sulfuric acid; boron trifluoride diethyl etherate; potassium carbonate; triethylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; tin(ll) chloride; lithium bromide; potassium hexacyanoferrate(III); diethylazodicarboxylate; In tetrahydrofuran; methanol; dichloromethane; water; toluene; tert-butyl alcohol;
DOI:10.1039/a605128f

Reference yield:

: 176209-06-6
(S)-1-(2-Furyl)-2-methoxy-N-tosylethylamine

: 189152-08-7
Benzoic acid (2S,3S,4R,5S)-4,5-dihydroxy-2-methoxymethyl-1-(toluene-4-sulfonyl)-piperidin-3-yl ester

Guidance literature:: Multi-step reaction with 8 steps

1: 89.2 percent / m-CPBA / CH₂Cl₂ / 14 h / Ambient temperature

2: 68.6 percent / BF₃*OEt₂, MS 4A / tetrahydrofuran / 3 h / 0 °C

3: 72.2 percent / CeCl₃*7H₂O, NaBH₄ / methanol / 1 h / -30 °C

4: 86.6 percent / DEAD, PPh₃ / tetrahydrofuran / 3 h / Ambient temperature

5: 83.3 percent / NaBH₄, 88percent formic acid / 1 h / 0 °C

6: 80.9 percent / (DHQ)2-PHAL, OsO₄, K₃Fe(CN)6, K₂CO₃ / 2-methyl-propan-2-ol; H₂O; toluene / 48 h / Ambient temperature

7: 1.) Et₃N, SOCl₂, 2.) RuCl₃*3H₂O, NaIO₄ / 1.) CH₂Cl₂, 0 deg C, 30 min, 2.) CCl₄, CH₃CN, H₂O, 0 deg C, 2 h

8: 82 percent / 50percent aq. H₂SO₄ / tetrahydrofuran / 24 h / 40 °C

With ruthenium trichloride; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; formic acid; thionyl chloride; cerium(III) chloride; (DHQ)2-PHAL; sulfuric acid; boron trifluoride diethyl etherate; potassium carbonate; triethylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; potassium hexacyanoferrate(III); diethylazodicarboxylate; In tetrahydrofuran; methanol; dichloromethane; water; toluene; tert-butyl alcohol;
DOI:10.1039/a605128f