Toluene-4-sulfonic acid (2R,3R)-2-hydroxy-4-methyl-3-methylsulfanylmethoxy-pent-4-enyl ester

Base Information

• Chemical Name: Toluene-4-sulfonic acid (2R,3R)-2-hydroxy-4-methyl-3-methylsulfanylmethoxy-pent-4-enyl ester
• CAS No.: 314280-92-7
• Molecular Formula: C₁₅H₂₂O₅S₂
• Molecular Weight: 346.469
• Mol file: 314280-92-7.mol

Synonyms:Toluene-4-sulfonic acid (2R,3R)-2-hydroxy-4-methyl-3-methylsulfanylmethoxy-pent-4-enyl ester

Chemical Property of Toluene-4-sulfonic acid (2R,3R)-2-hydroxy-4-methyl-3-methylsulfanylmethoxy-pent-4-enyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Toluene-4-sulfonic acid (2R,3R)-2-hydroxy-4-methyl-3-methylsulfanylmethoxy-pent-4-enyl ester

There total 3 articles about Toluene-4-sulfonic acid (2R,3R)-2-hydroxy-4-methyl-3-methylsulfanylmethoxy-pent-4-enyl 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: 75.0%

(2R,3R)-4-Methyl-3-methylsulfanylmethoxy-pent-4-ene-1,2-diol (314280-91-6) + p-toluenesulfonyl chloride (98-59-9) → Toluene-4-sulfonic acid (2R,3R)-2-hydroxy-4-methyl-3-methylsulfanylmethoxy-pent-4-enyl ester (314280-92-7)

Guidance literature:

With triethylamine; In dichloromethane; at 0 ℃; for 7h;

DOI:10.1021/ja0030820

Reference yield:

(R)-2,2-Dimethyl-4-((R)-2-methyl-1-methylsulfanylmethoxy-allyl)-[1,3]dioxolane (314280-90-5) → Toluene-4-sulfonic acid (2R,3R)-2-hydroxy-4-methyl-3-methylsulfanylmethoxy-pent-4-enyl ester (314280-92-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 88 percent / TsOH / methanol; H₂O / 2 h / 65 °C

2: 75 percent / Et₃N / CH₂Cl₂ / 7 h / 0 °C

With toluene-4-sulfonic acid; triethylamine; In methanol; dichloromethane; water;

DOI:10.1021/ja0030820

Reference yield:

(2R,3R)-1,2-O-isopropylidene-4-methyl-4-pentene-1,2,3-triol (139629-93-9) → Toluene-4-sulfonic acid (2R,3R)-2-hydroxy-4-methyl-3-methylsulfanylmethoxy-pent-4-enyl ester (314280-92-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 91 percent / AcOH; Ac₂O / 17 h / 20 °C

2: 88 percent / TsOH / methanol; H₂O / 2 h / 65 °C

3: 75 percent / Et₃N / CH₂Cl₂ / 7 h / 0 °C

With acetic anhydride; toluene-4-sulfonic acid; acetic acid; triethylamine; In methanol; dichloromethane; water;

DOI:10.1021/ja0030820

upstream raw materials:

(2R,3R)-4-Methyl-3-methylsulfanylmethoxy-pent-4-ene-1,2-diol

p-toluenesulfonyl chloride

(R)-2,2-Dimethyl-4-((R)-2-methyl-1-methylsulfanylmethoxy-allyl)-[1,3]dioxolane

(2R,3R)-1,2-O-isopropylidene-4-methyl-4-pentene-1,2,3-triol

Downstream raw materials:

Benzoic acid (2R,3R,5S,8S,13R,14S)-3-isopropenyl-8,14-dimethyl-15-oxo-1,2,3,6,7,8,11,12,13,14,15,17-dodecahydro-5H-4,16-dioxa-cyclopenta[a]phenanthren-2-yl ester

Benzoic acid (1R,2R)-1-((3aR,9aS,9bS)-9a,9b-dimethyl-1,7-dioxo-1,3,3a,4,5,7,8,9,9a,9b-decahydro-naphtho[1,2-c]furan-6-ylmethyl)-3-methyl-2-methylsulfanylmethoxy-but-3-enyl ester

Benzoic acid (1R,2R)-1-[(1R,3aR,9aS,9bS)-7-(dimethyl-hydrazono)-1-methoxy-9a,9b-dimethyl-1,3,3a,4,5,7,8,9,9a,9b-decahydro-naphtho[1,2-c]furan-6-ylmethyl]-3-methyl-2-methylsulfanylmethoxy-but-3-enyl ester

Benzoic acid (1R,2R)-1-[(1S,3aR,9aS,9bS)-7-(dimethyl-hydrazono)-1-methoxy-9a,9b-dimethyl-1,3,3a,4,5,7,8,9,9a,9b-decahydro-naphtho[1,2-c]furan-6-ylmethyl]-3-methyl-2-methylsulfanylmethoxy-but-3-enyl ester