calicoferol B

Base Information

• Chemical Name: calicoferol B
• CAS No.: 134624-75-2
• Molecular Formula: C₂₇H₄₄O₃
• Molecular Weight: 416.645
• DSSTox Substance ID: DTXSID801103885
• Nikkaji Number: J1.786.347I
• Wikidata: Q105344089
• Metabolomics Workbench ID: 171937
• ChEMBL ID: CHEMBL464351
• Mol file: 134624-75-2.mol

Synonyms:(-)-calicoferol B;calicoferol B

Chemical Property of calicoferol B

Chemical Property:

• XLogP3: 7.1
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 8
• Exact Mass: 416.32904526
• Heavy Atom Count: 30
• Complexity: 534

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1=C(C=C(C=C1)O)CCC2C(CCC3(C2CC(C3C(C)CCCC(C)C)O)C)O
• Isomeric SMILES: CC1=C(C=C(C=C1)O)CC[C@@H]2[C@@H](CC[C@]3([C@H]2C[C@@H]([C@@H]3[C@H](C)CCCC(C)C)O)C)O

Technology Process of calicoferol B

There total 16 articles about calicoferol B 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: 55.0%

(1R,2S,3aS,4S,5R,7aS)-1-((R)-1,5-Dimethyl-hexyl)-4-[2-(5-methoxy-2-methyl-phenyl)-ethyl]-7a-methyl-octahydro-indene-2,5-diol (444926-68-5) → Calicoferol B (134624-75-2)

Guidance literature:

(1R,2S,3aS,4S,5R,7aS)-1-((R)-1,5-Dimethyl-hexyl)-4-[2-(5-methoxy-2-methyl-phenyl)-ethyl]-7a-methyl-octahydro-indene-2,5-diol; With triethylsilane; tris(pentafluorophenyl)borate; In dichloromethane; at 20 ℃; for 1h;

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 24h; Further stages.;

DOI:10.1021/jo020103v

Reference yield:

C21H34O3 (276244-50-9) → Calicoferol B (134624-75-2)

Guidance literature:

Multi-step reaction with 13 steps

1.1: LDA / tetrahydrofuran / 1 h / -78 °C

1.2: 14 percent Turnov_. / tetrahydrofuran / -78 - 20 °C

2.1: triethyl orthoformate; p-TsOH*H₂O / CH₂Cl₂ / 72 h / 20 °C

2.2: 18 percent / p-TsOH*H₂O / ethanol / 48 h / 20 °C

3.1: 86 percent / triethyl orthoformate; p-TsOH*H₂O / CH₂Cl₂ / 72 h / 20 °C

4.1: 86 percent Turnov_. / pyridine / CH₂Cl₂ / 0 - 20 °C

5.1: 89 percent / DIBAL-H / tetrahydrofuran; hexane / 2 h / -78 - 20 °C

6.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C

6.2: 88 percent / tetrahydrofuran; hexane / 7.5 h / -78 - 20 °C

7.1: 43 mg / Na; EtOH / tetrahydrofuran / 2 h / -20 °C

8.1: 34 mg / Dess-Martin periodinane / CH₂Cl₂ / 1.5 h / 20 °C

9.1: tetrahydrofuran / 0 °C

9.2: 17 percent / HCl / tetrahydrofuran; methanol; H₂O / 4.5 h / Heating

10.1: 69 percent Turnov_. / KI / acetic acid / 48 h / 20 °C

11.1: CuI / diethyl ether / 1 h / -20 °C

11.2: 66 percent / diethyl ether / 1 h / -20 °C

12.1: 45 percent / L-Selectride / tetrahydrofuran / 2 h / -78 - 20 °C

13.1: Et₃SiH; (C₆F₅)3B / CH₂Cl₂ / 1 h / 20 °C

13.2: 55 percent / TBAF / tetrahydrofuran / 24 h / 20 °C

With pyridine; triethylsilane; copper(l) iodide; n-butyllithium; ethanol; tris(pentafluorophenyl)borate; sodium; L-Selectride; diisobutylaluminium hydride; Dess-Martin periodane; toluene-4-sulfonic acid; orthoformic acid triethyl ester; potassium iodide; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; acetic acid; 8.1: Dess-Martin reaction;

DOI:10.1021/jo020103v

Reference yield:

C24H38O5 (444926-42-5) → Calicoferol B (134624-75-2)

Guidance literature:

Multi-step reaction with 12 steps

1.1: triethyl orthoformate; p-TsOH*H₂O / CH₂Cl₂ / 72 h / 20 °C

1.2: 18 percent / p-TsOH*H₂O / ethanol / 48 h / 20 °C

2.1: 86 percent / triethyl orthoformate; p-TsOH*H₂O / CH₂Cl₂ / 72 h / 20 °C

3.1: 86 percent Turnov_. / pyridine / CH₂Cl₂ / 0 - 20 °C

4.1: 89 percent / DIBAL-H / tetrahydrofuran; hexane / 2 h / -78 - 20 °C

5.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C

5.2: 88 percent / tetrahydrofuran; hexane / 7.5 h / -78 - 20 °C

6.1: 43 mg / Na; EtOH / tetrahydrofuran / 2 h / -20 °C

7.1: 34 mg / Dess-Martin periodinane / CH₂Cl₂ / 1.5 h / 20 °C

8.1: tetrahydrofuran / 0 °C

8.2: 17 percent / HCl / tetrahydrofuran; methanol; H₂O / 4.5 h / Heating

9.1: 69 percent Turnov_. / KI / acetic acid / 48 h / 20 °C

10.1: CuI / diethyl ether / 1 h / -20 °C

10.2: 66 percent / diethyl ether / 1 h / -20 °C

11.1: 45 percent / L-Selectride / tetrahydrofuran / 2 h / -78 - 20 °C

12.1: Et₃SiH; (C₆F₅)3B / CH₂Cl₂ / 1 h / 20 °C

12.2: 55 percent / TBAF / tetrahydrofuran / 24 h / 20 °C

With pyridine; triethylsilane; copper(l) iodide; n-butyllithium; ethanol; tris(pentafluorophenyl)borate; sodium; L-Selectride; diisobutylaluminium hydride; Dess-Martin periodane; toluene-4-sulfonic acid; orthoformic acid triethyl ester; potassium iodide; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; acetic acid; 7.1: Dess-Martin reaction;

DOI:10.1021/jo020103v

upstream raw materials:

(1R,2S,3aS,4S,5R,7aS)-1-((R)-1,5-Dimethyl-hexyl)-4-[2-(5-methoxy-2-methyl-phenyl)-ethyl]-7a-methyl-octahydro-indene-2,5-diol

4-methoxy-2-<(phenylsulfonyl)methyl>benzaldehyde

4-bromo-1-methoxy-3-[(phenylsulfonyl)methyl]benzene

C₂₁H₃₄O₃