Thyrsiferyl 23-acetate

Base Information

• Chemical Name: Thyrsiferyl 23-acetate
• CAS No.: 96304-95-9
• Molecular Formula: C₃₂H₅₅BrO₈
• Molecular Weight: 647.688
• Nikkaji Number: J1.440.799E
• Wikidata: Q104956617
• Metabolomics Workbench ID: 124388
• ChEMBL ID: CHEMBL17664
• Mol file: 96304-95-9.mol

Synonyms:TF23A;thyrsiferyl 23-acetate

Chemical Property of Thyrsiferyl 23-acetate

Chemical Property:

• Vapor Pressure: 2.43E-20mmHg at 25°C
• Boiling Point: 662°Cat760mmHg
• Flash Point: 354.1°C
• PSA: 103.68000
• Density: 1.213g/cm³
• LogP: 5.75440
• XLogP3: 4.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 9
• Exact Mass: 646.30803
• Heavy Atom Count: 41
• Complexity: 958

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OC(C)(C)C1CCC(O1)(C)C(CCC(C)(C2CCC3C(O2)(CCC(O3)C4(CCC(C(O4)(C)C)Br)C)C)O)O
• Isomeric SMILES: CC(=O)OC(C)(C)[C@H]1CC[C@](O1)(C)[C@H](CC[C@@](C)([C@H]2CC[C@@H]3[C@@](O2)(CC[C@@H](O3)[C@@]4(CC[C@H](C(O4)(C)C)Br)C)C)O)O

Technology Process of Thyrsiferyl 23-acetate

There total 39 articles about Thyrsiferyl 23-acetate 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: 42.0%

thyrsiferyl 18,23-diacetate (96304-94-8) → Thyrsiferyl-23-acetate (96304-95-9) + thyrsiferol (93453-12-4,105880-10-2,116502-09-1,66873-39-0)

Guidance literature:

With potassium carbonate; In methanol; at 20 ℃; for 9h;

DOI:10.1021/ja000001r

Reference yield:

(2S,3S)-2,3-epoxygeraniol (82188-73-6) → Thyrsiferyl-23-acetate (96304-95-9)

Guidance literature:

Multi-step reaction with 13 steps

1.1: NaH / tetrahydrofuran / 0.33 h / 0 °C

1.2: 98 percent / Bu₄NI / tetrahydrofuran / 0 - 20 °C

2.1: 73 percent / aq. HClO₄ / tetrahydrofuran / 0 - 20 °C

3.1: 88 percent / pyridine / 18 h / 20 °C

4.1: 77 percent / Rhenium heptoxide; trifluoroacetic anhydride / CH₂Cl₂; acetonitrile

5.1: 70 percent / Sc(OTf)3 / acetonitrile / 0 - 20 °C

6.1: 98 percent / H₂ / Pd(OH)2/C / methanol; ethyl acetate / 2 h / 760.05 Torr

7.1: 88 percent / Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 0.75 h / 20 °C

8.1: 88 percent / CrCl₂ / tetrahydrofuran / 16 h / 20 °C

9.1: 62 percent / CrCl₂; NiCl₂ / dimethylsulfoxide / 21 h / 20 °C

10.1: 88 percent / NaHCO₃; Dess-Martin periodinane / CH₂Cl₂ / 1 h / 20 °C

11.1: 90 percent / H₂ / Pd/C / ethyl acetate / 5 h / 760.05 Torr

12.1: 87 percent / tetrahydrofuran; diethyl ether / 5 h / -78 °C

13.1: 35 percent / K₂CO₃ / methanol / 9 h / 20 °C

With pyridine; chromium dichloride; perchloric acid; hydrogen; sodium hydride; sodium hydrogencarbonate; potassium carbonate; Dess-Martin periodane; rhenium(VII) oxide; trifluoroacetic anhydride; nickel dichloride; scandium tris(trifluoromethanesulfonate); palladium dihydroxide; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; dimethyl sulfoxide; ethyl acetate; acetonitrile;

DOI:10.1021/ja000001r

Reference yield:

(5R)-2,3,4,5-tetrahydro-5-hydroxymethyl-2-furanone (52813-63-5) → Thyrsiferyl-23-acetate (96304-95-9)

Guidance literature:

Multi-step reaction with 21 steps

1.1: 74 percent / trifluoromethanesulfonic acid / CH₂Cl₂; pentane / 0.5 h / 0 °C

2.1: DIBAL / toluene / 1 h / -78 °C

3.1: 2.53 g / benzene / 2 h / Heating

4.1: 98 percent / imidazole / dimethylformamide / 0 - 20 °C

5.1: 72 percent / DIBAL / CH₂Cl₂ / 0.5 h / -78 °C

6.1: 86 percent / (-)-D-Diethyl tartrate; itanium isopropoxide; tert-butylhydroperoxide / 4 A molecular sieves / CH₂Cl₂; decane / 4 h / -20 °C

7.1: 95 percent / SO₃*Pyr; Et₃N / CH₂Cl₂; dimethylsulfoxide / 4 h / 0 °C

8.1: PPh₃ / CH₂Cl₂ / 0.33 h / 0 °C

8.2: 91 percent / NEt₃ / CH₂Cl₂ / 0.87 h / -78 °C

9.1: 88 percent / TBAF / tetrahydrofuran / 0 - 20 °C

10.1: 91 percent / borontrifluoride etherate / CH₂Cl₂ / -78 - -10 °C

11.1: 85 percent / imidazole / dimethylformamide / 0 - 20 °C

12.1: 75 percent / CrCl₂/NiCl₂ / dimethylformamide / 5 h / 20 °C

13.1: 89 percent / MnO₂ / hexane / 7 h / 20 °C

14.1: 98 percent / H₂ / Pd(OH)2/C / methanol / 2 h / 760.05 Torr

15.1: 76 percent / Et₃SiH; TMSOTf / CH₂Cl₂ / 0.5 h / -35 °C

16.1: 94 percent / Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 1 h / 20 °C

17.1: 62 percent / CrCl₂; NiCl₂ / dimethylsulfoxide / 21 h / 20 °C

18.1: 88 percent / NaHCO₃; Dess-Martin periodinane / CH₂Cl₂ / 1 h / 20 °C

19.1: 90 percent / H₂ / Pd/C / ethyl acetate / 5 h / 760.05 Torr

20.1: 87 percent / tetrahydrofuran; diethyl ether / 5 h / -78 °C

21.1: 35 percent / K₂CO₃ / methanol / 9 h / 20 °C

With 1H-imidazole; chromium dichloride; titanium(IV) isopropylate; triethylsilane; tert.-butylhydroperoxide; manganese(IV) oxide; pyridine-SO₃ complex; diethyl (2S,3S)-tartrate; trifluorormethanesulfonic acid; trimethylsilyl trifluoromethanesulfonate; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; hydrogen; diisobutylaluminium hydride; sodium hydrogencarbonate; potassium carbonate; Dess-Martin periodane; triethylamine; triphenylphosphine; nickel dichloride; palladium dihydroxide; palladium on activated charcoal; 4 A molecular sieve; In tetrahydrofuran; methanol; diethyl ether; decane; hexane; dichloromethane; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide; toluene; pentane; benzene; 6.1: Sharpless asymmetric epoxidation;

DOI:10.1021/ja000001r

upstream raw materials:

Acetic acid 1-((2R,5R)-5-{(1S,4S)-1,4-dihydroxy-4-[(2R,4aR,6R,8aS)-6-((S)-1-hydroxy-1,5-dimethyl-hex-4-enyl)-8a-methyl-octahydro-pyrano[3,2-b]pyran-2-yl]-pentyl}-5-methyl-tetrahydro-furan-2-yl)-1-methyl-ethyl ester

thyrsiferyl 18,23-diacetate

(2S,3S)-2,3-epoxygeraniol

(5R)-2,3,4,5-tetrahydro-5-hydroxymethyl-2-furanone

Downstream raw materials:

thyrsiferol

Acetic acid (1R,4S)-4-[(4aS,6S,8aR)-6-((2R,5S)-5-bromo-2,6,6-trimethyl-tetrahydro-pyran-2-yl)-8a-methyl-octahydro-pyrano[3,2-b]pyran-2-yl]-4-hydroxy-1-[(2R,5R)-5-(1-hydroxy-1-methyl-ethyl)-2-methyl-tetrahydro-furan-2-yl]-pentyl ester