Jaborosalactone B

Base Information

• Chemical Name: Jaborosalactone B
• CAS No.: 6105-16-4
• Molecular Formula: C28H38O5
• Molecular Weight: 454.5983
• NSC Number: 109438
• DSSTox Substance ID: DTXSID90976543
• Nikkaji Number: J15.984K
• Wikidata: Q82961458
• Metabolomics Workbench ID: 136745
• ChEMBL ID: CHEMBL465076
• Mol file: 6105-16-4.mol

Synonyms:Jaborosalactone B;6105-16-4;NSC109438;CHEMBL465076;DTXSID90976543;NSC-109438;6,27-dihydroxy-22,26-epoxyergosta-2,4,24-triene-1,26-dione

Chemical Property of Jaborosalactone B

Chemical Property:

• Vapor Pressure: 1.77E-20mmHg at 25°C
• Boiling Point: 664.3°Cat760mmHg
• Flash Point: 220.4°C
• Density: 1.22g/cm³
• XLogP3: 4.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 454.27192431
• Heavy Atom Count: 33
• Complexity: 959

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(C(=O)OC(C1)C(C)C2CCC3C2(CCC4C3CC(C5=CC=CC(=O)C45C)O)C)CO
• Isomeric SMILES: CC1=C(C(=O)O[C@H](C1)[C@@H](C)[C@H]2CC[C@@H]3[C@@]2(CC[C@H]4[C@H]3C[C@H](C5=CC=CC(=O)[C@]45C)O)C)CO

Technology Process of Jaborosalactone B

There total 11 articles about Jaborosalactone 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:

(R)-6-[(S)-1-((1S,3R,8S,9S,10R,13S,14S,17R)-1,3-Bis-methoxymethoxy-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-ethyl]-4-methyl-5,6-dihydro-pyran-2-one (81426-81-5) → jaborosalactone B (6105-16-4)

Guidance literature:

Multi-step reaction with 11 steps

1: H₂, NaHCO₃ / 5percent Pd-C / dioxane

2: 1.) LICHA / 1.) THF, -78 deg C, 2.) HMPA, THF, -78 deg C

3: 1.) LICHA / 1.) THF, -78 deg C, 2.) -78 deg C

4: aq. HCl / tetrahydrofuran

5: imidazole / dimethylformamide

6: 1.) m-CPBA / 1.) CHCl₃, -78 deg C, 2.) neat, 100 deg C

7: i-Pr₂NEt / CH₂Cl₂

8: PDC / dimethylformamide

10: m-CPBA / CH₂Cl₂

11: 5percent aq. KOH / tetrahydrofuran

With 1H-imidazole; hydrogenchloride; potassium hydroxide; dipyridinium dichromate; hydrogen; sodium hydrogencarbonate; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ja00377a039

Reference yield:

jaborosalactone A (5788-94-3) → jaborosalactone B (6105-16-4)

Guidance literature:

With potassium hydroxide; In tetrahydrofuran;

DOI:10.1021/ja00377a039

Reference yield:

(R)-6-[(S)-1-((8S,9S,10R,13S,14S,17R)-10,13-Dimethyl-1-oxo-4,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl)-ethyl]-3-hydroxymethyl-4-methyl-5,6-dihydro-pyran-2-one (81874-44-4) → jaborosalactone B (6105-16-4)

Guidance literature:

Multi-step reaction with 2 steps

1: m-CPBA / CH₂Cl₂

2: 5percent aq. KOH / tetrahydrofuran

With potassium hydroxide; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; dichloromethane;

DOI:10.1021/ja00377a039

upstream raw materials:

jaborosalactone A

(R)-6-[(S)-1-((8S,9S,10R,13S,14S,17R)-10,13-Dimethyl-1-oxo-4,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl)-ethyl]-3-hydroxymethyl-4-methyl-5,6-dihydro-pyran-2-one

(R)-6-[(S)-1-((1S,3R,8S,9S,10R,13S,14S,17R)-1,3-Bis-methoxymethoxy-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-ethyl]-4-methyl-5,6-dihydro-pyran-2-one

(4R,6R)-6-[(S)-1-((1S,3R,8S,9S,10R,13S,14S,17R)-1,3-Bis-methoxymethoxy-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-ethyl]-4-methyl-tetrahydro-pyran-2-one

Refernces