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

Base Information

• Chemical Name: Benzoic acid (3aR,6R,7R,7aS)-6-methoxymethyl-2,2-dioxo-5-(toluene-4-sulfonyl)-hexahydro-1,3-dioxa-2λ⁶-thia-5-aza-inden-7-yl ester
• CAS No.: 189151-32-4
• Molecular Formula: C₂₁H₂₃NO₉S₂
• Molecular Weight: 497.547
• Mol file: 189151-32-4.mol

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

Chemical Property of Benzoic acid (3aR,6R,7R,7aS)-6-methoxymethyl-2,2-dioxo-5-(toluene-4-sulfonyl)-hexahydro-1,3-dioxa-2λ⁶-thia-5-aza-inden-7-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Benzoic acid (3aR,6R,7R,7aS)-6-methoxymethyl-2,2-dioxo-5-(toluene-4-sulfonyl)-hexahydro-1,3-dioxa-2λ⁶-thia-5-aza-inden-7-yl ester

There total 7 articles about Benzoic acid (3aR,6R,7R,7aS)-6-methoxymethyl-2,2-dioxo-5-(toluene-4-sulfonyl)-hexahydro-1,3-dioxa-2λ⁶-thia-5-aza-inden-7-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:

N-tosylfurfurylamine (121564-33-8) → Benzoic acid (3aR,6R,7R,7aS)-6-methoxymethyl-2,2-dioxo-5-(toluene-4-sulfonyl)-hexahydro-1,3-dioxa-2λ6-thia-5-aza-inden-7-yl ester (189151-32-4)

Guidance literature:

Multi-step reaction with 7 steps

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

2: 76.5 percent / BF₃*OEt₂, MS 4A / tetrahydrofuran / 3 h / 0 °C

3: 72.3 percent / CeCl₃*7H₂O, NaBH₄ / methanol / 1 h / -30 °C

4: 91.7 percent / DEAD, PPh₃ / tetrahydrofuran / 3 h / Ambient temperature

5: 86.7 percent / NaBH₄, 88percent formic acid / 1 h / 0 °C

6: 84.4 percent / (DHQ)2-PHAL, OsO₄, K₃Fe(CN)6, K₂CO₃ / 2-methyl-propan-2-ol; H₂O / 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

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

DOI:10.1039/a605128f

Reference yield:

(2R,3R,6R)-1-Tosyl-6-ethoxy-2-methoxymethyl-1,2,3,6-tetrahydropyridin-3-ol (176209-10-2) → Benzoic acid (3aR,6R,7R,7aS)-6-methoxymethyl-2,2-dioxo-5-(toluene-4-sulfonyl)-hexahydro-1,3-dioxa-2λ6-thia-5-aza-inden-7-yl ester (189151-32-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 91.7 percent / DEAD, PPh₃ / tetrahydrofuran / 3 h / Ambient temperature

2: 86.7 percent / NaBH₄, 88percent formic acid / 1 h / 0 °C

3: 84.4 percent / (DHQ)2-PHAL, OsO₄, K₃Fe(CN)6, K₂CO₃ / 2-methyl-propan-2-ol; H₂O / 48 h / Ambient temperature

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

With ruthenium trichloride; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; formic acid; thionyl chloride; (DHQ)2-PHAL; potassium carbonate; triethylamine; triphenylphosphine; potassium hexacyanoferrate(III); diethylazodicarboxylate; In tetrahydrofuran; water; tert-butyl alcohol;

DOI:10.1039/a605128f

Reference yield:

(2R,3S)-1-Tosyl-2-methoxymethyl-1,2,3,6-tetrahydro-3-pyridyl benzoate (176209-12-4) → Benzoic acid (3aR,6R,7R,7aS)-6-methoxymethyl-2,2-dioxo-5-(toluene-4-sulfonyl)-hexahydro-1,3-dioxa-2λ6-thia-5-aza-inden-7-yl ester (189151-32-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 84.4 percent / (DHQ)2-PHAL, OsO₄, K₃Fe(CN)6, K₂CO₃ / 2-methyl-propan-2-ol; H₂O / 48 h / Ambient temperature

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

With ruthenium trichloride; sodium periodate; osmium(VIII) oxide; thionyl chloride; (DHQ)2-PHAL; potassium carbonate; triethylamine; potassium hexacyanoferrate(III); In water; tert-butyl alcohol;

DOI:10.1039/a605128f

upstream raw materials:

N-tosylfurfurylamine

(2R,6R)-N-Tosyl-6-hydroxy-2-methoxymethyl-1,2,3,6-tetrahydropyridin-3-one

(2R,3R,6R)-1-Tosyl-6-ethoxy-2-methoxymethyl-1,2,3,6-tetrahydropyridin-3-ol

(2R,6R)-N-Tosyl-6-ethoxy-2-methoxymethyl-1,2,3,6-tetrahydropyridin-3-one

Downstream raw materials:

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

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

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