Toluene-4-sulfonic acid (3S,3aR,4R,4aS,8aR,9aS)-3-methyl-1-oxo-dodecahydro-naphtho[2,3-c]furan-4-ylmethyl ester

Base Information

• Chemical Name: Toluene-4-sulfonic acid (3S,3aR,4R,4aS,8aR,9aS)-3-methyl-1-oxo-dodecahydro-naphtho[2,3-c]furan-4-ylmethyl ester
• CAS No.: 192133-55-4
• Molecular Formula: C₂₁H₂₈O₅S
• Molecular Weight: 392.516
• Mol file: 192133-55-4.mol

Synonyms:Toluene-4-sulfonic acid (3S,3aR,4R,4aS,8aR,9aS)-3-methyl-1-oxo-dodecahydro-naphtho[2,3-c]furan-4-ylmethyl ester

Chemical Property of Toluene-4-sulfonic acid (3S,3aR,4R,4aS,8aR,9aS)-3-methyl-1-oxo-dodecahydro-naphtho[2,3-c]furan-4-ylmethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Toluene-4-sulfonic acid (3S,3aR,4R,4aS,8aR,9aS)-3-methyl-1-oxo-dodecahydro-naphtho[2,3-c]furan-4-ylmethyl ester

There total 2 articles about Toluene-4-sulfonic acid (3S,3aR,4R,4aS,8aR,9aS)-3-methyl-1-oxo-dodecahydro-naphtho[2,3-c]furan-4-ylmethyl 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: 95.0%

p-toluenesulfonyl chloride (98-59-9) + (3S,3aR,4R,4aS,8aR,9aS)-4-Hydroxymethyl-3-methyl-decahydro-naphtho[2,3-c]furan-1-one (168416-98-6) → Toluene-4-sulfonic acid (3S,3aR,4R,4aS,8aR,9aS)-3-methyl-1-oxo-dodecahydro-naphtho[2,3-c]furan-4-ylmethyl ester (192133-55-4)

Guidance literature:

With pyridine; 0 deg C, 2 h; 4 deg C, overnight;

DOI:10.1021/jo970612a

Reference yield:

(3S,3aR,4R,4aS,8aS)-3-Methyl-1-oxo-1,3,3a,4,4a,5,6,7,8,8a-decahydro-naphtho[2,3-c]furan-4-carbothioic acid S-ethyl ester (168416-97-5) → Toluene-4-sulfonic acid (3S,3aR,4R,4aS,8aR,9aS)-3-methyl-1-oxo-dodecahydro-naphtho[2,3-c]furan-4-ylmethyl ester (192133-55-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 81 percent / Raney nickel / diethyl ether; ethanol / 0.5 h / Ambient temperature

2: 95 percent / pyridine / 0 deg C, 2 h; 4 deg C, overnight

With pyridine; nickel; In diethyl ether; ethanol;

DOI:10.1021/jo970612a

Reference yield: 94.0%

thiophenol (108-98-5) + Toluene-4-sulfonic acid (3S,3aR,4R,4aS,8aR,9aS)-3-methyl-1-oxo-dodecahydro-naphtho[2,3-c]furan-4-ylmethyl ester (192133-55-4) → (3S,3aS,4R,4aS,8aR,9aS)-3-Methyl-4-phenylsulfanylmethyl-decahydro-naphtho[2,3-c]furan-1-one (168417-00-3)

Guidance literature:

With potassium tert-butylate; In dimethyl sulfoxide; for 1h; Ambient temperature;

DOI:10.1021/jo970612a

upstream raw materials:

p-toluenesulfonyl chloride

(3S,3aR,4R,4aS,8aR,9aS)-4-Hydroxymethyl-3-methyl-decahydro-naphtho[2,3-c]furan-1-one

(3S,3aR,4R,4aS,8aS)-3-Methyl-1-oxo-1,3,3a,4,4a,5,6,7,8,8a-decahydro-naphtho[2,3-c]furan-4-carbothioic acid S-ethyl ester

Downstream raw materials:

(3S,3aS,4R,4aS,8aR,9aS)-3-Methyl-4-phenylsulfanylmethyl-decahydro-naphtho[2,3-c]furan-1-one

himbacine

(3S,3aS,4R,4aS,8aR,9aS)-3-Methyl-4-phenylsulfanylmethyl-dodecahydro-naphtho[2,3-c]furan-1-ol

himbeline