Tagitinins

Base Information

• Chemical Name: Tagitinins
• CAS No.: 59979-58-7
• Molecular Formula: C19H26O6
• Molecular Weight: 350.4061
• DSSTox Substance ID: DTXSID601318171
• Mol file: 59979-58-7.mol

Synonyms:tagitinin;tagitinin A;tagitinin B;tagitinin C;tagitinin D;tagitinin F;tagitinins

Chemical Property of Tagitinins

Chemical Property:

• Vapor Pressure: 6.35E-13mmHg at 25°C
• Boiling Point: 518.6°Cat760mmHg
• Flash Point: 182.5°C
• PSA: 85.36000
• Density: 1.22g/cm³
• LogP: 1.91050
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 3
• Exact Mass: 350.17293854
• Heavy Atom Count: 25
• Complexity: 636

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1=CC2C(C(CC3(C(O3)CC1O)C)OC(=O)C(C)C)C(=C)C(=O)O2
• Isomeric SMILES: C/C/1=C\C2C(C(CC3(C(O3)CC1O)C)OC(=O)C(C)C)C(=C)C(=O)O2

Technology Process of Tagitinins

There total 5 articles about Tagitinins 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:

Isobutyric acid (Z)-(1aR,5aS,9R,10aR)-4,10a-dimethyl-8-morpholin-4-ylmethyl-3,7-dioxo-1a,2,3,5a,7,8,8a,9,10,10a-decahydro-1,6-dioxa-cyclopenta[a]cyclopropa[e]cyclodecen-9-yl ester (72301-74-7) → tagitinin E (59979-58-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 14 mg / NaBH₄ / propan-2-ol / 4 h / -15 °C

2: 10 mg / CH₃I / Ambient temperature

With sodium tetrahydroborate; methyl iodide; In isopropyl alcohol;

DOI:10.1021/jo01291a038

Reference yield:

Isobutyric acid (6E,10Z)-(4R,11aS)-6,10-dimethyl-3-methylene-2,9-dioxo-2,3,3a,4,5,8,9,11a-octahydro-cyclodeca[b]furan-4-yl ester (72301-72-5) → tagitinin E (59979-58-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 10 mg / perbenzoic acid / CHCl₃ / 12 h / 0 °C

2: 25 mg / ethanol / 12 h / 0 °C

3: 14 mg / NaBH₄ / propan-2-ol / 4 h / -15 °C

4: 10 mg / CH₃I / Ambient temperature

With sodium tetrahydroborate; Perbenzoic acid; methyl iodide; In ethanol; chloroform; isopropyl alcohol;

DOI:10.1021/jo01291a038

Reference yield:

Isobutyric acid (Z)-(1aR,5aS,9R,10aR)-4,10a-dimethyl-8-methylene-3,7-dioxo-1a,2,3,5a,7,8,8a,9,10,10a-decahydro-1,6-dioxa-cyclopenta[a]cyclopropa[e]cyclodecen-9-yl ester (72301-73-6) → tagitinin E (59979-58-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 25 mg / ethanol / 12 h / 0 °C

2: 14 mg / NaBH₄ / propan-2-ol / 4 h / -15 °C

3: 10 mg / CH₃I / Ambient temperature

With sodium tetrahydroborate; methyl iodide; In ethanol; isopropyl alcohol;

DOI:10.1021/jo01291a038

upstream raw materials:

Isobutyric acid (Z)-(1aR,3S,5aS,9R,10aR)-3-hydroxy-4,10a-dimethyl-8-morpholin-4-ylmethyl-7-oxo-1a,2,3,5a,7,8,8a,9,10,10a-decahydro-1,6-dioxa-cyclopenta[a]cyclopropa[e]cyclodecen-9-yl ester

Isobutyric acid (Z)-(1aR,5aS,9R,10aR)-4,10a-dimethyl-8-morpholin-4-ylmethyl-3,7-dioxo-1a,2,3,5a,7,8,8a,9,10,10a-decahydro-1,6-dioxa-cyclopenta[a]cyclopropa[e]cyclodecen-9-yl ester

Isobutyric acid (6E,10Z)-(4R,11aS)-6,10-dimethyl-3-methylene-2,9-dioxo-2,3,3a,4,5,8,9,11a-octahydro-cyclodeca[b]furan-4-yl ester

Isobutyric acid (Z)-(1aR,5aS,9R,10aR)-4,10a-dimethyl-8-methylene-3,7-dioxo-1a,2,3,5a,7,8,8a,9,10,10a-decahydro-1,6-dioxa-cyclopenta[a]cyclopropa[e]cyclodecen-9-yl ester

Refernces