(1S,5S,6S,7S)-4,10,10-Trimethyl-3,3-dioxo-5,6-bis-phenylethynyl-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]decan-6-ol

Base Information

• Chemical Name: (1S,5S,6S,7S)-4,10,10-Trimethyl-3,3-dioxo-5,6-bis-phenylethynyl-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]decan-6-ol
• CAS No.: 185134-86-5
• Molecular Formula: C₂₇H₂₇NO₃S
• Molecular Weight: 445.582
• Mol file: 185134-86-5.mol

Synonyms:(1S,5S,6S,7S)-4,10,10-Trimethyl-3,3-dioxo-5,6-bis-phenylethynyl-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]decan-6-ol

Chemical Property of (1S,5S,6S,7S)-4,10,10-Trimethyl-3,3-dioxo-5,6-bis-phenylethynyl-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]decan-6-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,5S,6S,7S)-4,10,10-Trimethyl-3,3-dioxo-5,6-bis-phenylethynyl-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]decan-6-ol

There total 2 articles about (1S,5S,6S,7S)-4,10,10-Trimethyl-3,3-dioxo-5,6-bis-phenylethynyl-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]decan-6-ol 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:

(3aS)-8,8-dimethyl-5,6-dihydro-3H-3a,6-methano-2,1-benzoisothiazol-7(4H)-one 2,2-dioxide (119106-38-6) → (1S,5S,6S,7S)-4,10,10-Trimethyl-3,3-dioxo-5,6-bis-phenylethynyl-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]decan-6-ol (185134-86-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) BuLi / 1.) Et₂O, hexane, RT, 30 min, 2.) Et₂O, hexane, reflux, 12 h

2: 1.) NaH / 1.) THF, RT, 30 min, 2.) THF, RT, 12 h

With n-butyllithium; sodium hydride;

DOI:10.1515/znb-1996-1121

Reference yield:

dimethyl sulfate (77-78-1) + (1S,5S,6S,7S)-10,10-Dimethyl-3,3-dioxo-5,6-bis-phenylethynyl-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]decan-6-ol (185134-85-4) → (1S,5S,6S,7S)-4,10,10-Trimethyl-3,3-dioxo-5,6-bis-phenylethynyl-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]decan-6-ol (185134-86-5)

Guidance literature:

With sodium hydride; Yield given. Multistep reaction; 1.) THF, RT, 30 min, 2.) THF, RT, 12 h;

DOI:10.1515/znb-1996-1121

Reference yield: 97.0%

(1S,5S,6S,7S)-4,10,10-Trimethyl-3,3-dioxo-5,6-bis-phenylethynyl-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]decan-6-ol (185134-86-5) → (3aS,6aS,9aR)-6a-hydroxy-7-iodo-9-(Z-2-iodo-2-phenylmethylene)-1,10,10-trimethyl-8-phenyl-3,3a,4,5,6,6a-hexahydro-1H,9H-3a,6-methano-indeno[3a,4-c]isothiazole 2,2-dioxide

Guidance literature:

With iodine; In dichloromethane;

DOI:10.1515/znb-1996-1121

upstream raw materials:

dimethyl sulfate

(1S,5S,6S,7S)-10,10-Dimethyl-3,3-dioxo-5,6-bis-phenylethynyl-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]decan-6-ol

(3aS)-8,8-dimethyl-5,6-dihydro-3H-3a,6-methano-2,1-benzoisothiazol-7(4H)-one 2,2-dioxide