7-Deoxypaclitaxel

Base Information

• Chemical Name: 7-Deoxypaclitaxel
• CAS No.: 149705-85-1
• Molecular Formula: C₄₇H₅₁NO₁₃
• Molecular Weight: 837.921
• DSSTox Substance ID: DTXSID201317888
• Nikkaji Number: J548.319K
• ChEMBL ID: CHEMBL203365
• Mol file: 149705-85-1.mol

Synonyms:7-deoxypaclitaxel

Chemical Property of 7-Deoxypaclitaxel

Chemical Property:

• XLogP3: 3.5
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 13
• Rotatable Bond Count: 14
• Exact Mass: 837.33604068
• Heavy Atom Count: 61
• Complexity: 1760

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1=C2C(C(=O)C3(CCC4C(C3C(C(C2(C)C)(CC1OC(=O)C(C(C5=CC=CC=C5)NC(=O)C6=CC=CC=C6)O)O)OC(=O)C7=CC=CC=C7)(CO4)OC(=O)C)C)OC(=O)C
• Isomeric SMILES: CC1=C2[C@H](C(=O)[C@@]3(CC[C@@H]4[C@]([C@H]3[C@@H]([C@@](C2(C)C)(C[C@@H]1OC(=O)[C@@H]([C@H](C5=CC=CC=C5)NC(=O)C6=CC=CC=C6)O)O)OC(=O)C7=CC=CC=C7)(CO4)OC(=O)C)C)OC(=O)C

Technology Process of 7-Deoxypaclitaxel

There total 36 articles about 7-Deoxypaclitaxel 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:

9-O-Acetyl-5-O-cinnamoyltaxicine I (146257-44-5) → 7-deoxypaclitaxel (149705-85-1)

Guidance literature:

Multi-step reaction with 16 steps

1: KOAc / methanol / 12 h / 20 °C

2: pyridine / CH₂Cl₂ / 0.5 h / 0 °C

3: H₂O; imidazole / diethyl ether / 0.17 h / 20 °C

4: 80 percent / Dess-Martin periodinane; TFA / CH₂Cl₂ / 12 h / 20 °C

5: 100 percent / NMO; OsO₄; H₂O / tetrahydrofuran; 2-methyl-propan-2-ol / 12 h / 20 °C

6: 80 percent / KOAc / 0.37 h / Heating

7: 83 percent / DMAP; NEt₃ / CH₂Cl₂ / 24 h / 20 °C

8: 97 percent / pyridine / 24 h / 20 °C

9: 80 percent / HF / acetonitrile / 6.5 h / 20 °C

10: 82 percent / diisopropylamine / toluene / 39 h / Heating

11: 66 percent / DMAP / CH₂Cl₂ / 4 h / 20 °C

12: tetrahydrofuran / 0.5 h / -78 °C

13: DMAP / CH₂Cl₂ / 1 h / 20 °C

14: 83 percent / NaBH₄ / methanol / 3 h / 20 °C

15: DCC; DMAP / tetrahydrofuran / 1 h / 20 °C

16: TsOH; MeOH / 2 h / 20 °C

With pyridine; 1H-imidazole; methanol; dmap; sodium tetrahydroborate; osmium(VIII) oxide; N-methyl-2-indolinone; hydrogen fluoride; water; potassium acetate; Dess-Martin periodane; toluene-4-sulfonic acid; triethylamine; diisopropylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; toluene; acetonitrile; tert-butyl alcohol; 1: Isomerization / 2: Cyclization / 3: Hydrolysis / 4: Oxidation / 5: Oxidation / 6: Methanolysis / 7: Etherification / 8: Mesylation / 9: Desilylation / 10: Cyclization / 11: Acetylation / 12: Ring cleavage / 13: Acetylation / 14: Reduction / 15: Esterification / 16: Ring cleavage;

Reference yield:

7-deshydroxy baccatine III (150930-83-9) → 7-deoxypaclitaxel (149705-85-1)

Guidance literature:

Multi-step reaction with 2 steps

1: DCC; DMAP / tetrahydrofuran / 1 h / 20 °C

2: TsOH; MeOH / 2 h / 20 °C

With methanol; dmap; toluene-4-sulfonic acid; dicyclohexyl-carbodiimide; In tetrahydrofuran; 1: Esterification / 2: Ring cleavage;

Reference yield:

10-O-Acetyl-5-O-cinnamoyltaxicine 1,2-carbonate (214192-64-0) → 7-deoxypaclitaxel (149705-85-1)

Guidance literature:

Multi-step reaction with 13 steps

1: 80 percent / Dess-Martin periodinane; TFA / CH₂Cl₂ / 12 h / 20 °C

2: 100 percent / NMO; OsO₄; H₂O / tetrahydrofuran; 2-methyl-propan-2-ol / 12 h / 20 °C

3: 80 percent / KOAc / 0.37 h / Heating

4: 83 percent / DMAP; NEt₃ / CH₂Cl₂ / 24 h / 20 °C

5: 97 percent / pyridine / 24 h / 20 °C

6: 80 percent / HF / acetonitrile / 6.5 h / 20 °C

7: 82 percent / diisopropylamine / toluene / 39 h / Heating

8: 66 percent / DMAP / CH₂Cl₂ / 4 h / 20 °C

9: tetrahydrofuran / 0.5 h / -78 °C

10: DMAP / CH₂Cl₂ / 1 h / 20 °C

11: 83 percent / NaBH₄ / methanol / 3 h / 20 °C

12: DCC; DMAP / tetrahydrofuran / 1 h / 20 °C

13: TsOH; MeOH / 2 h / 20 °C

With pyridine; methanol; dmap; sodium tetrahydroborate; osmium(VIII) oxide; N-methyl-2-indolinone; hydrogen fluoride; water; potassium acetate; Dess-Martin periodane; toluene-4-sulfonic acid; triethylamine; diisopropylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; In tetrahydrofuran; methanol; dichloromethane; toluene; acetonitrile; tert-butyl alcohol; 1: Oxidation / 2: Oxidation / 3: Methanolysis / 4: Etherification / 5: Mesylation / 6: Desilylation / 7: Cyclization / 8: Acetylation / 9: Ring cleavage / 10: Acetylation / 11: Reduction / 12: Esterification / 13: Ring cleavage;

upstream raw materials:

(3R,4S)-1-benzoyl-4-phenyl-3-(triethylsilyl)oxy-2-azetidinone

7-deshydroxy baccatine III

C₅₃H₆₅NO₁₃Si

C₅₅H₆₇NO₁₄S₂Si

Downstream raw materials:

10-deacetoxy-paclitaxel

2'-O-TBDMS-7-O-TES-9,10-diketo-paclitaxel

C₅₂H₆₃NO₁₃Si

C₅₄H₆₇NO₁₄Si