Thyrsiferol

Base Information

• Chemical Name: Thyrsiferol
• CAS No.: 66873-39-0
• Molecular Formula: C30H53BrO7
• Molecular Weight: 605.64
• Nikkaji Number: J1.334.798K
• Wikidata: Q105112165
• Metabolomics Workbench ID: 127754
• ChEMBL ID: CHEMBL2272771
• Mol file: 66873-39-0.mol

Synonyms:thyrsiferol

Chemical Property of Thyrsiferol

Chemical Property:

• XLogP3: 3.6
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 7
• Exact Mass: 604.29747
• Heavy Atom Count: 38
• Complexity: 853

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1(C(CCC(O1)(C)C2CCC3(C(O2)CCC(O3)C(C)(CCC(C4(CCC(O4)C(C)(C)O)C)O)O)C)Br)C
• Isomeric SMILES: C[C@]12CC[C@@H](O[C@@H]1CC[C@@H](O2)[C@](C)(CC[C@@H]([C@]3(CC[C@@H](O3)C(C)(C)O)C)O)O)[C@@]4(CC[C@H](C(O4)(C)C)Br)C

Technology Process of Thyrsiferol

There total 50 articles about Thyrsiferol 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) → thyrsiferol (93453-12-4,105880-10-2,116502-09-1,66873-39-0)

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: 42 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) → thyrsiferol (93453-12-4,105880-10-2,116502-09-1,66873-39-0)

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: 42 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:

(2R,4aR,6R,8aS)-Octahydro-2-<(1S,4S)-1,4-dihydroxy-4-<(2R,5R)-tetrahydro-5-(1-hydroxy-1-methylethyl)-2-methylfuran-2-yl>-1-methylbutyl>-6-<(S)-1-hydroxy-1,5-dimethylhex-4-enyl>-8a-methylpyrano<3,2-b>pyran

thyrsifenyl 23-acetate

(R)-3-{2-[(2R,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]-oxiranyl}-1-[(2R,5R)-5-(1-hydroxy-1-methyl-ethyl)-2-methyl-tetrahydro-furan-2-yl]-propan-1-ol

magireol-A

Downstream raw materials:

thyrsiferyl 18-acetate

thyrsiferol monoacetate

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

Refernces

• 1、 Hashimoto, Masaru,Kan, Toshiyuki,Nozaki, Koji,Yanagiya, Mitsutoshi,Shirahama, Harushia,Matsumoto, Takeshi. "Total Syntheses of (+)-Thyrsiferol, (+)-Thyrsiferyl 23-Acetate, and (+)-Venustatriol". . p. 5088 - 5107. Retrieved 2007/10/02.
• 2、 Suzuki, Teruaki,Takeda, Satoshi,Suzuki, Minoru,Kurosawa, Etsuro,Kato, Arata,Imanaka, Yoshihiko. "Cytotoxic Squalene-Derived Polyethers from the Marine Red Alga Laurentia obtusa (Hudson) Lamouroux". . p. 361 - 364. Retrieved 2007/10/02.