7,8-Didehydro-3,3',8'-trihydroxy-b,k-carotene-6'-one

Base Information

• Chemical Name: 7,8-Didehydro-3,3',8'-trihydroxy-b,k-carotene-6'-one
• CAS No.: 50906-61-1
• Molecular Formula: C₄₀H₅₄O₄
• Molecular Weight: 598.866
• Mol file: 50906-61-1.mol

Synonyms:7,8-Didehydro-3,3',8'-trihydroxy-b,k-carotene-6'-one;(3R,3'S,5'R)-7,8-Didehydro-3,3',8'-trihydroxy-beta,kappa-caroten-6'-one

Chemical Property of 7,8-Didehydro-3,3',8'-trihydroxy-b,k-carotene-6'-one

Chemical Property:

• XLogP3: 10.3
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 11
• Exact Mass: 598.40221020
• Heavy Atom Count: 44
• Complexity: 1430

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1=C(C(CC(C1)O)(C)C)C#CC(=CC=CC(=CC=CC=C(C)C=CC=C(C)C(=CC(=O)C2(CC(CC2(C)C)O)C)O)C)C
• Isomeric SMILES: CC1=C(C(CC(C1)O)(C)C)C#C/C(=C/C=C/C(=C/C=C/C=C(\C)/C=C/C=C(\C)/C(=C/C(=O)C2(CC(CC2(C)C)O)C)/O)/C)/C

Technology Process of 7,8-Didehydro-3,3',8'-trihydroxy-b,k-carotene-6'-one

There total 28 articles about 7,8-Didehydro-3,3',8'-trihydroxy-b,k-carotene-6'-one 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: 97.0%

C46H68O4Si → all-E mytiloxanthin (50906-61-1)

Guidance literature:

With pyridinium p-toluenesulfonate;

DOI:10.3390/md14050093

Reference yield:

(1R,4S,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-1-(tert-butyl-dimethyl-silanyloxymethyl)-2,2,6-trimethyl-7-oxa-bicyclo[4.1.0]heptane (214335-85-0) → all-E mytiloxanthin (50906-61-1)

Guidance literature:

Multi-step reaction with 7 steps

1: boron trifluoride diethyl etherate

2: sodium tetrahydroborate

4: lithium hexamethyldisilazane / tetrahydrofuran / 50 °C

5: toluene-4-sulfonic acid

6: sodium methylate

7: pyridinium p-toluenesulfonate

With sodium tetrahydroborate; boron trifluoride diethyl etherate; sodium methylate; pyridinium p-toluenesulfonate; toluene-4-sulfonic acid; lithium hexamethyldisilazane; In tetrahydrofuran;

DOI:10.3390/md14050093

Reference yield:

C16H32O2Si → all-E mytiloxanthin (50906-61-1)

Guidance literature:

Multi-step reaction with 4 steps

1: lithium hexamethyldisilazane / tetrahydrofuran / 50 °C

2: toluene-4-sulfonic acid

3: sodium methylate

4: pyridinium p-toluenesulfonate

With sodium methylate; pyridinium p-toluenesulfonate; toluene-4-sulfonic acid; lithium hexamethyldisilazane; In tetrahydrofuran;

DOI:10.3390/md14050093

upstream raw materials:

(2E,4E,6E,8E/Z,10E,12E)-12-hydroxy-14-[(1R,4S)-4-hydroxy-1,2,2-trimethylcyclopentyl]-2,7,11-trimethyl-14-oxotetradeca-2,4,6,8,10,12-hexaenal

[(4R)-4-tert-butyldimethylsilyloxy-2,6,6-trimethylcyclohex-1-enyl]acetaldehyde

2-[(4R)-4-tert-butyldimethylsilyloxy-2,6,6-trimethylcyclohex-1-enyl]ethanol

(2E,4E)-4-acetyloxy-6-[(1R,4S)-4-hydroxy-1,2,2-trimethylcyclopentyl]-3-methyl-6-oxohexa-2,4-dienal

Downstream raw materials:

mytiloxanthin diacetate

Refernces

First total synthesis of mytiloxanthin

10.1248/cpb.48.1833

The research describes the first total synthesis of mytiloxanthin 2, a compound with a unique cyclopentyl enolic β-diketone group conjugated to the polyene chain. The purpose of this study was to achieve the biomimetic total synthesis of mytiloxanthin 2 using a stereoselective rearrangement of epoxides. Important reagents include p-methoxybenzyloxymethyl (PMBM) chloride for protection, LiAlH? for reduction, o-iodoxybenzoic acid (IBX) for oxidation, and vinyl bromide 13 for the introduction of the C10-unit. The synthesis involved several steps, including the reduction of ketone 7 to obtain compound 11, conversion to aldehyde 12, and subsequent oxidation to yield ketone 14. The final steps involved the protection of the diketone moiety with an acetyl group to form acetate 17, partial deprotection with tetrabutylammonium fluoride (TBAF), oxidation with IBX, and final deprotection with HF to obtain the cis-β-diketone-aldehyde 8b. The cis-aldehyde 8b was then reacted with the C10-phosphonium salt 19 in the presence of KOH to form an isomeric mixture, which was condensed with the acetylenic Wittig salt 20 to yield mytiloxanthin 2. The spectral data of the synthesized mytiloxanthin 2 were in good agreement with those of a natural specimen, confirming the successful total synthesis.