(8aS,8bS)-6,6,8b-Trimethyl-3-(toluene-4-sulfonyl)-4,6,7,8,8a,8b-hexahydro-naphtho[1,8-bc]furan-2-one

Base Information

• Chemical Name: (8aS,8bS)-6,6,8b-Trimethyl-3-(toluene-4-sulfonyl)-4,6,7,8,8a,8b-hexahydro-naphtho[1,8-bc]furan-2-one
• CAS No.: 123286-35-1
• Molecular Formula: C₂₁H₂₄O₄S
• Molecular Weight: 372.485

Synonyms:(8aS,8bS)-6,6,8b-Trimethyl-3-(toluene-4-sulfonyl)-4,6,7,8,8a,8b-hexahydro-naphtho[1,8-bc]furan-2-one

Chemical Property of (8aS,8bS)-6,6,8b-Trimethyl-3-(toluene-4-sulfonyl)-4,6,7,8,8a,8b-hexahydro-naphtho[1,8-bc]furan-2-one

Chemical Property:

Purity/Quality:

Safty Information:

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Useful:

Technology Process of (8aS,8bS)-6,6,8b-Trimethyl-3-(toluene-4-sulfonyl)-4,6,7,8,8a,8b-hexahydro-naphtho[1,8-bc]furan-2-one

There total 10 articles about (8aS,8bS)-6,6,8b-Trimethyl-3-(toluene-4-sulfonyl)-4,6,7,8,8a,8b-hexahydro-naphtho[1,8-bc]furan-2-one 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: 72.0%

3-(p-toluenesulfonyl)propiolic acid (114250-62-3) + 2,4,4-trimethyl-3-vinyl-cyclohex-2-enol (114298-66-7) → (8aR,8bR)-6,6,8b-Trimethyl-3-(toluene-4-sulfonyl)-4,6,7,8,8a,8b-hexahydro-naphtho[1,8-bc]furan-2-one (114250-63-4,123286-35-1)

Guidance literature:

In chloroform; at 23 ℃; for 30h;

DOI:10.1021/ja00219a059

Reference yield: 64.0%

(Toluene-4-sulfonyl)-propynoic acid (S)-2,4,4-trimethyl-3-vinyl-cyclohex-2-enyl ester (123218-27-9) → (8aS,8bS)-6,6,8b-Trimethyl-3-(toluene-4-sulfonyl)-4,6,7,8,8a,8b-hexahydro-naphtho[1,8-bc]furan-2-one (123286-35-1)

Guidance literature:

In dichloromethane; at 23 ℃; for 36h;

DOI:10.1016/S0040-4039(00)82359-X

Reference yield:

ethynyl p-tolyl sulfone (13894-21-8) → (8aR,8bR)-6,6,8b-Trimethyl-3-(toluene-4-sulfonyl)-4,6,7,8,8a,8b-hexahydro-naphtho[1,8-bc]furan-2-one (114250-63-4,123286-35-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) BuLi / 1.) THF, -105 to -95 deg C, 2.) THF, -95 to 0 deg C

2: 72 percent / CHCl₃ / 30 h / 23 °C

With n-butyllithium; In chloroform;

DOI:10.1021/ja00219a059

upstream raw materials:

(Toluene-4-sulfonyl)-propynoic acid (S)-2,4,4-trimethyl-3-vinyl-cyclohex-2-enyl ester

ethynyl p-tolyl sulfone

3-(p-toluenesulfonyl)propiolic acid

(Z)-3-Iodo-3-(toluene-4-sulfonyl)-acrylic acid (S)-2,4,4-trimethyl-3-vinyl-cyclohex-2-enyl ester

Downstream raw materials:

(1S,4aR,8R,8aR)-8-Benzoyloxy-2,5,5,8a-tetramethyl-4-oxo-1,4,4a,5,6,7,8,8a-octahydro-naphthalene-1-carboxylic acid

(1S,4aR,8R,8aR)-8-Benzoyloxy-2,5,5,8a-tetramethyl-4-oxo-1,4,4a,5,6,7,8,8a-octahydro-naphthalene-1-carboxylic acid methyl ester

Benzoic acid (1R,5S,6S,7S,8R)-8-hydroxy-2,2,6,8-tetramethyl-12-oxo-11-oxa-tricyclo[5.3.2.0^1,6]dodec-9-en-5-yl ester

C₃₀H₃₉NO₉Se

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