Taxusin

Base Information

• Chemical Name: Taxusin
• CAS No.: 19605-80-2
• Molecular Formula: C₂₈H₄₀O₈
• Molecular Weight: 504.621
• UNII: VHS5792RP7
• DSSTox Substance ID: DTXSID90941377
• Nikkaji Number: J148.880E
• Wikipedia: Taxusin
• Wikidata: Q15427894
• Metabolomics Workbench ID: 62882
• ChEMBL ID: CHEMBL368741
• Mol file: 19605-80-2.mol

Synonyms:taxusin

Chemical Property of Taxusin

Chemical Property:

• Vapor Pressure: 1.29E-11mmHg at 25°C
• Melting Point: 131～132℃
• Boiling Point: 537.3°Cat760mmHg
• Flash Point: 224.4°C
• PSA: 105.20000
• Density: 1.16g/cm³
• LogP: 4.45200
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 8
• Exact Mass: 504.27231823
• Heavy Atom Count: 36
• Complexity: 992

Purity/Quality:

NLT 98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C2C(C(C3(CCC(C(=C)C3CC(C2(C)C)CC1OC(=O)C)OC(=O)C)C)OC(=O)C)OC(=O)C
• Isomeric SMILES: CC1=C2[C@H]([C@@H]([C@@]3(CC[C@@H](C(=C)[C@H]3C[C@@H](C2(C)C)C[C@@H]1OC(=O)C)OC(=O)C)C)OC(=O)C)OC(=O)C

Technology Process of Taxusin

There total 47 articles about Taxusin 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: 85.0%

Taxa-4(16),11-dien-5α,9α-10β,13α-tetraol (15877-46-0) + acetic anhydride (108-24-7) → Taxusin (19605-80-2,116002-25-6)

Guidance literature:

With dmap; triethylamine; In dichloromethane; for 20h; Ambient temperature;

DOI:10.1021/ja980538t

Reference yield:

(R)-3-Benzyloxymethyl-5-[(S)-2-(bis-benzyloxy-methyl)-6-hydroxy-cyclohex-1-enylmethyl]-2,4,4-trimethyl-cyclohex-2-enone (226910-57-2) → taxusin (116002-25-6,19605-80-2)

Guidance literature:

Multi-step reaction with 18 steps

1: Ph₃P / tetrahydrofuran / 0.17 h / -23 °C

2: tetrahydrofuran / 168 h / Ambient temperature

3: t-BuOK / tetrahydrofuran / 1 h / 0 °C

4: tetrahydrofuran / 1 h / -78 °C

5: TMSOTf / CH₂Cl₂ / 1 h / -78 °C

6: 70 percent / TiCl₃(O-i-Pr) / CH₂Cl₂ / 1 h / -78 °C

7: lithium tri(t-butoxy)aluminum hydride / tetrahydrofuran / Ambient temperature

8: 2,6-lutidine / CH₂Cl₂ / 1 h / -23 °C

9: DIBAL / CH₂Cl₂; hexane / 1 h / -78 °C

10: diethylzinc / diethyl ether; hexane / 6 h / Ambient temperature

11: PDC, 4A molecular sieves / CH₂Cl₂ / 1.5 h / Ambient temperature

12: TBAF

13: 1.) Li, liq. NH₃, t-BuOH, 2.) MeOH / 1.) THF, -78 deg C, 1 h, 2.) THF, RT, 1 h

14: LDA, Et₃N / CH₂Cl₂; hexane / 0.67 h / -78 - 0 °C

15: m-CPBA, KHCO₃ / CH₂Cl₂ / 0.17 h / 0 °C

16: 0.25 N aq. HCl / tetrahydrofuran / 1 h

17: Et₃N, DMAP / CH₂Cl₂ / 1.5 h / 0 °C

18: 1.) n-BuLi / 1.) toluene, hexane, 0 deg C, 1.5 h, 2.) toluene, hexane, RT, overnight

With 2,6-dimethylpyridine; hydrogenchloride; methanol; dmap; dipyridinium dichromate; n-butyllithium; titanium(IV) trichloride isopropoxide; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; potassium tert-butylate; tetrabutyl ammonium fluoride; ammonia; diethylzinc; lithium; diisobutylaluminium hydride; potassium hydrogencarbonate; lithium tri-t-butoxyaluminum hydride; triethylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; tert-butyl alcohol; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; hexane; dichloromethane;

DOI:10.1021/ja984250f

Reference yield:

2,2-Dimethyl-propionic acid (R)-2-((R)-3-benzyloxymethyl-2,2,4-trimethyl-5-oxo-cyclohex-3-enylmethyl)-3-(bis-benzyloxy-methyl)-cyclohex-2-enyl ester (226910-58-3) → taxusin (116002-25-6,19605-80-2)

Guidance literature:

Multi-step reaction with 16 steps

1: t-BuOK / tetrahydrofuran / 1 h / 0 °C

2: tetrahydrofuran / 1 h / -78 °C

3: TMSOTf / CH₂Cl₂ / 1 h / -78 °C

4: 70 percent / TiCl₃(O-i-Pr) / CH₂Cl₂ / 1 h / -78 °C

5: lithium tri(t-butoxy)aluminum hydride / tetrahydrofuran / Ambient temperature

6: 2,6-lutidine / CH₂Cl₂ / 1 h / -23 °C

7: DIBAL / CH₂Cl₂; hexane / 1 h / -78 °C

8: diethylzinc / diethyl ether; hexane / 6 h / Ambient temperature

9: PDC, 4A molecular sieves / CH₂Cl₂ / 1.5 h / Ambient temperature

10: TBAF

11: 1.) Li, liq. NH₃, t-BuOH, 2.) MeOH / 1.) THF, -78 deg C, 1 h, 2.) THF, RT, 1 h

12: LDA, Et₃N / CH₂Cl₂; hexane / 0.67 h / -78 - 0 °C

13: m-CPBA, KHCO₃ / CH₂Cl₂ / 0.17 h / 0 °C

14: 0.25 N aq. HCl / tetrahydrofuran / 1 h

15: Et₃N, DMAP / CH₂Cl₂ / 1.5 h / 0 °C

16: 1.) n-BuLi / 1.) toluene, hexane, 0 deg C, 1.5 h, 2.) toluene, hexane, RT, overnight

With 2,6-dimethylpyridine; hydrogenchloride; methanol; dmap; dipyridinium dichromate; n-butyllithium; titanium(IV) trichloride isopropoxide; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; potassium tert-butylate; tetrabutyl ammonium fluoride; ammonia; diethylzinc; lithium; diisobutylaluminium hydride; potassium hydrogencarbonate; lithium tri-t-butoxyaluminum hydride; triethylamine; 3-chloro-benzenecarboperoxoic acid; tert-butyl alcohol; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; hexane; dichloromethane;

DOI:10.1021/ja984250f

upstream raw materials:

Taxa-4(16),11-dien-5α,9α-10β,13α-tetraol

acetic anhydride

(3S,4aR,6R,8S,9Z,11R,12R,12aR)-1,2,3,4,4a,5,6,7,8,11,12,12a-dodecahydro-11,12-(isopropylidenedioxy)-3-(methoxymethoxy)-9,12a,13,13-tetramethyl-4-methylene-6,10-methanobenzocyclodecen-8-ol

(3S,4aR,6R,9Z,11R,12R,12aR)-1,3,4,4a,5,6,7,11,12,12a-decahydro-11,12-(isopropylidenedioxy)-3-(methoxymethoxy)-12a,13,13-trimethyl-4-methylene-6,10-methanobenzocyclodecen-8(2H)-one

Refernces

• 1、 Paquette, Leo A.,Wang, Hui-Ling,Su, Zhuang,Zhao, Mangzhu. "Enantiospecific total synthesis of natural (+)-taxusin. 2. Functionalization of the A-ring and arrival at the target". . p. 5213 - 5225. Retrieved 2007/10/03.