(8S)-8beta-Acetyl-7,8,9,10-tetrahydro-6,8alpha,11-trihydroxy-1-methoxy-10alpha-[3-(trifluoroacetylamino)-2,3,6-trideoxy-alpha-L-arabino-hexopyranosyloxy]-5,12-naphthacenedione

Base Information

• Chemical Name: (8S)-8beta-Acetyl-7,8,9,10-tetrahydro-6,8alpha,11-trihydroxy-1-methoxy-10alpha-[3-(trifluoroacetylamino)-2,3,6-trideoxy-alpha-L-arabino-hexopyranosyloxy]-5,12-naphthacenedione
• CAS No.: 57918-22-6
• Molecular Formula: C29H28F3NO11
• Molecular Weight: 623.537
• DSSTox Substance ID: DTXSID601099125
• Nikkaji Number: J296.824J
• Mol file: 57918-22-6.mol

Synonyms:VOASREXNXKOKBP-VMPUWYRSSA-N;DTXSID601099125;4'-epi-N-Trifluoroacetyldaunorubicin;(8S)-8beta-Acetyl-7,8,9,10-tetrahydro-6,8alpha,11-trihydroxy-1-methoxy-10alpha-[3-(trifluoroacetylamino)-2,3,6-trideoxy-alpha-L-arabino-hexopyranosyloxy]-5,12-naphthacenedione;NS00054470;(8S,10S)-8-Acetyl-7,8,9,10-tetrahydro-6,8,11-trihydroxy-1-methoxy-10-[[2,3,6-trideoxy-3-[(2,2,2-trifluoroacetyl)amino]-alpha-L-arabino-hexopyranosyl]oxy]-5,12-naphthacenedione

Chemical Property of (8S)-8beta-Acetyl-7,8,9,10-tetrahydro-6,8alpha,11-trihydroxy-1-methoxy-10alpha-[3-(trifluoroacetylamino)-2,3,6-trideoxy-alpha-L-arabino-hexopyranosyloxy]-5,12-naphthacenedione

Chemical Property:

• Boiling Point: 817°Cat760mmHg
• Flash Point: 447.9°C
• Density: 1.61g/cm³
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 14
• Rotatable Bond Count: 5
• Exact Mass: 623.16144520
• Heavy Atom Count: 44
• Complexity: 1170

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1C(C(CC(O1)OC2CC(CC3=C2C(=C4C(=C3O)C(=O)C5=C(C4=O)C(=CC=C5)OC)O)(C(=O)C)O)NC(=O)C(F)(F)F)O
• Isomeric SMILES: C[C@H]1[C@@H]([C@H](C[C@@H](O1)O[C@H]2C[C@@](CC3=C2C(=C4C(=C3O)C(=O)C5=C(C4=O)C(=CC=C5)OC)O)(C(=O)C)O)NC(=O)C(F)(F)F)O

Technology Process of (8S)-8beta-Acetyl-7,8,9,10-tetrahydro-6,8alpha,11-trihydroxy-1-methoxy-10alpha-[3-(trifluoroacetylamino)-2,3,6-trideoxy-alpha-L-arabino-hexopyranosyloxy]-5,12-naphthacenedione

There total 17 articles about (8S)-8beta-Acetyl-7,8,9,10-tetrahydro-6,8alpha,11-trihydroxy-1-methoxy-10alpha-[3-(trifluoroacetylamino)-2,3,6-trideoxy-alpha-L-arabino-hexopyranosyloxy]-5,12-naphthacenedione 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: 100.0%

4’-epidaunorubicin (57918-24-8) + trifluoroacetic anhydride (407-25-0) → 4'-epi-N-(trifluoroacetyl)daunorubicin (57918-22-6,52471-41-7,64686-33-5)

Guidance literature:

4’-epidaunorubicin; trifluoroacetic anhydride; In ethyl acetate; Inert atmosphere;

With sodium hydroxide; In methanol; ethyl acetate; at 20 ℃; for 1h;

Reference yield: 93.6%

4'-keto-N-trifluoroacetyl-daunorubicin (79441-78-4) → 4'-epi-N-(trifluoroacetyl)daunorubicin (57918-22-6,52471-41-7,64686-33-5)

Guidance literature:

With sodium tetrahydroborate; In methanol; ethanol; dichloromethane; at -3 - 3 ℃; for 1h; Inert atmosphere;

Reference yield:

3'-N-trifluoroacetyldaunorubicin (26388-52-3,52471-41-7,64686-33-5) → 4'-epi-N-(trifluoroacetyl)daunorubicin (57918-22-6,52471-41-7,64686-33-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 80 percent / methyl sulfoxide, trifluoroacetic anhydride, triethylamine / -70 °C

2: NaBH₄ / tetrahydrofuran

With sodium tetrahydroborate; dimethyl sulfoxide; triethylamine; trifluoroacetic anhydride; In tetrahydrofuran;

DOI:10.1016/S0008-6215(00)80821-6

upstream raw materials:

4'-keto-N-trifluoroacetyl-daunorubicin

3'-N-trifluoroacetyldaunorubicin

4’-epidaunorubicin

trifluoroacetic anhydride

Downstream raw materials:

chlorhydrate de 3,4-diepidaunorubicine

4’-epidaunorubicin

Refernces

• 1、 -. "A epirubicin than star intermediate body surface epidaunorubicin synthetic method (by machine translation)". Paragraph 0098; 0217-0228; 0278-0281. . Retrieved 2019/07/08.
• 2、 -. "Epirubicin hydrochloride intermediate compound IV". Paragraph 0197; 0198; 0199; 0200; 0205; 0206; 0212; 0213. . Retrieved 2017/09/01.