Cucurbitaxanthin A

Base Information

• Chemical Name: Cucurbitaxanthin A
• CAS No.: 103955-77-7
• Molecular Formula: C40H56 O3
• Molecular Weight: 584.883
• DSSTox Substance ID: DTXSID401315840
• Metabolomics Workbench ID: 28830
• Nikkaji Number: J710.162G
• Wikidata: Q63409473
• Mol file: 103955-77-7.mol

Synonyms:cucurbitaxanthin A

Chemical Property of Cucurbitaxanthin A

Chemical Property:

• XLogP3: 10.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 10
• Exact Mass: 584.42294564
• Heavy Atom Count: 43
• Complexity: 1330

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(C(CC(C1)O)(C)C)C=CC(=CC=CC(=CC=CC=C(C)C=CC=C(C)C=CC23C(CC(O2)CC3(C)O)(C)C)C)C
• Isomeric SMILES: CC1=C(C(C[C@@H](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@@]23[C@](C[C@@H](O2)CC3(C)C)(C)O)/C)/C

Technology Process of Cucurbitaxanthin A

There total 13 articles about Cucurbitaxanthin A 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: 54.0%

(3R,3'S,5'R,6'R)-3',6'-epoxy-5,6-dihydro-5'-triethylsilyloxy-β,β-caroten-3-ol (737763-65-4) → (all-E,3S,3'R,5R,6R)-3,6-epoxy-5,6-dihydro-β,β-carotene-3',5-diol (103955-77-7)

Guidance literature:

With tetrabutyl ammonium fluoride; acetic acid; at 50 ℃;

DOI:10.1248/cpb.52.780

Reference yield:

(-)-(1S,4S,6R)-4-(tert-butyldimethylsilyloxy)-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptane-1-carbaldehyde (439859-70-8) → (all-E,3S,3'R,5R,6R)-3,6-epoxy-5,6-dihydro-β,β-carotene-3',5-diol (103955-77-7)

Guidance literature:

Multi-step reaction with 9 steps

1: 80 percent / NaH

2: 96 percent / HF; pyridine

3: 54 percent / (BrC₆H₄)3NSbCl₆ / CH₂Cl₂ / 2 h / 20 °C

4: lutidine

5: DIBAL-H

6: NaOMe

7: Dowex 50W-X₈ (H+)

8: 56 percent / NaOMe

9: 54 percent / TBAF; AcOH / 50 °C

With pyridine; (BrC₆H₄)3NSbCl₆; Dowex 50W-X₈ (H+); lutidine; hydrogen fluoride; tetrabutyl ammonium fluoride; sodium methylate; sodium hydride; diisobutylaluminium hydride; acetic acid; In dichloromethane; 1: Emmons-Horner reaction / 6: Wittig condensation / 8: Wittig condensation;

DOI:10.1248/cpb.52.780

Reference yield:

(2E,4E)-5-[(1S,4S,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-2,2,6-trimethyl-7-oxa-bicyclo[4.1.0]hept-1-yl]-3-methyl-penta-2,4-dienoic acid ethyl ester (395089-70-0) → (all-E,3S,3'R,5R,6R)-3,6-epoxy-5,6-dihydro-β,β-carotene-3',5-diol (103955-77-7)

Guidance literature:

Multi-step reaction with 9 steps

1: 98 percent / HF; pyridine

2: 45 percent / (BrC₆H₄)3NSbCl₆ / CH₂Cl₂ / 0.33 h / 20 °C

3: lutidine

4: LiAlH₄

5: MnO₂

6: NaOMe

7: Dowex 50W-X₈ (H+)

8: 56 percent / NaOMe

9: 54 percent / TBAF; AcOH / 50 °C

With pyridine; manganese(IV) oxide; lithium aluminium tetrahydride; (BrC₆H₄)3NSbCl₆; Dowex 50W-X₈ (H+); lutidine; hydrogen fluoride; tetrabutyl ammonium fluoride; sodium methylate; acetic acid; In dichloromethane; 6: Wittig condensation / 8: Wittig condensation;

DOI:10.1248/cpb.52.780

upstream raw materials:

(3R,3'S,5'R,6'R)-3',6'-epoxy-5,6-dihydro-5'-triethylsilyloxy-β,β-caroten-3-ol

(2E,4E)-5-[(1S,4S,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-2,2,6-trimethyl-7-oxa-bicyclo[4.1.0]hept-1-yl]-3-methyl-penta-2,4-dienoic acid ethyl ester

(-)-(1S,4S,6R)-4-(tert-butyldimethylsilyloxy)-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptane-1-carbaldehyde

(2E,4E)-5-((1S,4S,6R)-4-Hydroxy-2,2,6-trimethyl-7-oxa-bicyclo[4.1.0]hept-1-yl)-3-methyl-penta-2,4-dienenitrile

Downstream raw materials:

zeaxanthin