TP808

Base Information

• Chemical Name: TP808
• CAS No.: 852821-06-8
• Molecular Formula: C26 H34N2O5Si
• Molecular Weight: 482.652
• Mol file: 852821-06-8.mol

Synonyms:Naphth[2,3-d]isoxazole-4,5(4aH,8H)-dione, 9-(dimethylamino)-4a-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-8a,9-dihydro -3-(phenylmethoxy)-, (4aS,8aS,9S)-

Chemical Property of TP808

Chemical Property:

• Melting Point: 150-151℃ (ethyl acetate hexane )
• Boiling Point: 573.8±50.0 °C(Predicted)
• PKA: 5.25±0.40(Predicted)
• PSA: 81.87000
• Density: 1.18±0.1 g/cm3(Predicted)
• LogP: 4.95840
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C

Purity/Quality:

min 99% ^*data from raw suppliers

(4aS,8aS,9S)-3-(Benzyloxy)-4a-((tert-butyldimethylsilyl)oxy)-9-(dimethylamino)-8a,9-dihydronaphtho[2,3-d]isoxazole-4,5(4aH,8H)-dione ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: (4aS,8aS,9S)-3-(Benzyloxy)-4a-((tert-butyldimethylsilyl)oxy)-9-(dimethylamino)-8a,9-dihydronaphtho[2,3-d]isoxazole-4,5(4aH,8H)-dione serves as a highly versatile intermediate for the construction of diverse tetracycline antibiotics. (4aS,8aS,9S)-3-(Benzyloxy)-4a-((tert-butyldimethylsilyl)oxy)-9-(dimethylamino)-8a,9-dihydronaphtho[2,3-d]isoxazole-4,5(4aH,8H)-dione serves as a highlyversatile intermediate for the construction of diverse tetracycline antibiotics.

Technology Process of TP808

There total 22 articles about TP808 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: 91.0%

C20H20N2O5 (856906-36-0) + t-butyldimethylsiyl triflate (69739-34-0) → (4aS,8aS,9S)-3-(benzyloxy)-4a-(tert-butyldimethylsilyloxy)-9-(dimethylamino)-8a,9-dihydronaphtho[2,3-d]isoxazole-4,5(4aH,8H)-dione (852821-06-8)

Guidance literature:

With 2,6-dimethylpyridine; In dichloromethane; water; at 23 ℃; for 3h; pH=7.0; Aqueous potassium phosphate buffer solution;

Reference yield: 46.0%

C21H22N2O5 + t-butyldimethylsiyl triflate (69739-34-0) → (4aS,8aS,9S)-3-(benzyloxy)-4a-(tert-butyldimethylsilyloxy)-9-(dimethylamino)-8a,9-dihydronaphtho[2,3-d]isoxazole-4,5(4aH,8H)-dione (852821-06-8)

Guidance literature:

C₂₁H₂₂N₂O₅; With boron tribromide; In dichloromethane; at -78 ℃; for 0.2h;

With water; In dichloromethane; Aqueous phosphate buffer;

t-butyldimethylsiyl triflate; With 2,6-dimethylpyridine; In dichloromethane; at 0 - 23 ℃; for 1.16667h;

Reference yield:

C20H22N2O5 + t-butyldimethylsiyl triflate (69739-34-0) → (4aS,8aS,9S)-3-(benzyloxy)-4a-(tert-butyldimethylsilyloxy)-9-(dimethylamino)-8a,9-dihydronaphtho[2,3-d]isoxazole-4,5(4aH,8H)-dione (852821-06-8)

Guidance literature:

With 2,6-dimethylpyridine; In dichloromethane; at 0 - 23 ℃; for 0.583333h;

upstream raw materials:

t-butyldimethylsiyl triflate

C₂₀H₂₀N₂O₅

C₂₁H₂₄N₂O₅

C₂₀H₂₀N₂O₅

Downstream raw materials:

C₃₃H₅₀N₂O₅S₂Si₂

C₃₂H₄₀N₂O₅SSi

((4aS,8aS,9S)-3-(benzyloxy)-5-((tert-butyldimethylsilyl)oxy)-9-(dimethylamino)-4a-hydroxy-8a,9-dihydronaphtho[2,3-d]isoxazol-4(4aH)-one)

C₄₀H₅₀N₂O₉Si

Refernces

• 1、 Zhang, Wu-Yan,Chen, Chi-Li,He, Minsheng,Zhu, Zhijian,Hogan, Philip,Gilicky, Olga,Dunwoody, Nicholas,Ronn, Magnus. "Process Research and Development of TP-808: A Key Intermediate for the Manufacture of Synthetic Tetracyclines". . p. 377 - 386. Retrieved 2017/03/24.
• 2、 -. "SYNTHESIS OF ENONE INTERMEDIATE". . . Retrieved 2008/12/08.