Mycosporine

Base Information

• Chemical Name: Mycosporine
• CAS No.: 59719-29-8
• Molecular Formula: C11H19NO6
• Molecular Weight: 261.27
• DSSTox Substance ID: DTXSID00331982
• Nikkaji Number: J667.925K
• Wikidata: Q27107431
• Metabolomics Workbench ID: 69478
• ChEMBL ID: CHEMBL1210424
• Mol file: 59719-29-8.mol

Synonyms:Mycosporine;Mycosporine Serinol;59719-29-8;CHEBI:7039;CHEMBL1210424;C10607;(5S)-3-(1,3-dihydroxypropan-2-ylamino)-5-hydroxy-5-(hydroxymethyl)-2-methoxycyclohex-2-en-1-one;AC1L9DJE;DTXSID00331982;Q27107431;(5S)-5-hydroxy-3-[[2-hydroxy-1-(hydroxymethyl)ethyl]amino]-5-(hydroxymethyl)-2-methoxy-cyclohex-2-en-1-one

Chemical Property of Mycosporine

Chemical Property:

• Vapor Pressure: 2.15E-15mmHg at 25°C
• Boiling Point: 570.6°C at 760 mmHg
• Flash Point: 298.9°C
• PSA: 119.25000
• Density: 1.39g/cm³
• LogP: -1.73560
• XLogP3: -2.4
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 6
• Exact Mass: 261.12123733
• Heavy Atom Count: 18
• Complexity: 338

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(CC(CC1=O)(CO)O)NC(CO)CO
• Isomeric SMILES: COC1=C(C[C@](CC1=O)(CO)O)NC(CO)CO

Technology Process of Mycosporine

There total 15 articles about Mycosporine 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:

(1S,3R,4R,5R)-3,4-O-Benzylidene-1,3,4-trihydroxy-6-oxabicyclo<3.2.1>octan-7-one (216662-57-6) → mycosporine serinol (59719-29-8)

Guidance literature:

Multi-step reaction with 12 steps

1: 76 percent / N-bromosuccinimide / CCl₄ / 1.3 h

2: 1.) NaBH₄, 2.) p-TsOH / 1.) i-PrOH, 2.) acetone, reflux, 2 h

3: 64 percent / PCC / CH₂Cl₂ / 11 h / Heating

4: 88 percent / dimethylformamide / 15 h / 25 °C

5: 99 percent / diethyl ether; ethyl acetate / 15 h / 0 °C

6: 62 percent / (i-Bu)2AlH / CH₂Cl₂ / 3 h / 0 °C

7: PCC, NaOAc / CH₂Cl₂ / 13 h / 25 °C

8: NaN₃ / LiCl / dimethylformamide / 15 h / 25 °C

9: 94 percent / diethyl ether / 3 h / 25 °C

10: 2.) NaBH₃CN / 1.) Et₂O, reflux, 2 h, 2.) MeOH, 25 deg C, 1 h

11: NaBH₄ / methanol; H₂O / 3 h / 0 °C

12: 50percent aq. TFA / 0.33 h / 0 °C

With sodium tetrahydroborate; N-Bromosuccinimide; sodium azide; sodium acetate; diisobutylaluminium hydride; sodium cyanoborohydride; toluene-4-sulfonic acid; pyridinium chlorochromate; trifluoroacetic acid; lithium chloride; In methanol; tetrachloromethane; diethyl ether; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/ja00206a059

Reference yield:

D-(-)-quinic acid (77-95-2) → mycosporine serinol (59719-29-8)

Guidance literature:

Multi-step reaction with 13 steps

1: 97 percent / p-TsOH / benzene / 19 h / Heating

2: 76 percent / N-bromosuccinimide / CCl₄ / 1.3 h

3: 1.) NaBH₄, 2.) p-TsOH / 1.) i-PrOH, 2.) acetone, reflux, 2 h

4: 64 percent / PCC / CH₂Cl₂ / 11 h / Heating

5: 88 percent / dimethylformamide / 15 h / 25 °C

6: 99 percent / diethyl ether; ethyl acetate / 15 h / 0 °C

7: 62 percent / (i-Bu)2AlH / CH₂Cl₂ / 3 h / 0 °C

8: PCC, NaOAc / CH₂Cl₂ / 13 h / 25 °C

9: NaN₃ / LiCl / dimethylformamide / 15 h / 25 °C

10: 94 percent / diethyl ether / 3 h / 25 °C

11: 2.) NaBH₃CN / 1.) Et₂O, reflux, 2 h, 2.) MeOH, 25 deg C, 1 h

12: NaBH₄ / methanol; H₂O / 3 h / 0 °C

13: 50percent aq. TFA / 0.33 h / 0 °C

With sodium tetrahydroborate; N-Bromosuccinimide; sodium azide; sodium acetate; diisobutylaluminium hydride; sodium cyanoborohydride; toluene-4-sulfonic acid; pyridinium chlorochromate; trifluoroacetic acid; lithium chloride; In methanol; tetrachloromethane; diethyl ether; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; benzene;

DOI:10.1021/ja00206a059

Reference yield:

(1R,3S,4S,5R)-3-bromo-1-hydroxy-7-oxo-6-oxabicyclo[3.2.1]oct-4-yl benzoate (105539-78-4) → mycosporine serinol (59719-29-8)

Guidance literature:

Multi-step reaction with 11 steps

1: 1.) NaBH₄, 2.) p-TsOH / 1.) i-PrOH, 2.) acetone, reflux, 2 h

2: 64 percent / PCC / CH₂Cl₂ / 11 h / Heating

3: 88 percent / dimethylformamide / 15 h / 25 °C

4: 99 percent / diethyl ether; ethyl acetate / 15 h / 0 °C

5: 62 percent / (i-Bu)2AlH / CH₂Cl₂ / 3 h / 0 °C

6: PCC, NaOAc / CH₂Cl₂ / 13 h / 25 °C

7: NaN₃ / LiCl / dimethylformamide / 15 h / 25 °C

8: 94 percent / diethyl ether / 3 h / 25 °C

9: 2.) NaBH₃CN / 1.) Et₂O, reflux, 2 h, 2.) MeOH, 25 deg C, 1 h

10: NaBH₄ / methanol; H₂O / 3 h / 0 °C

11: 50percent aq. TFA / 0.33 h / 0 °C

With sodium tetrahydroborate; sodium azide; sodium acetate; diisobutylaluminium hydride; sodium cyanoborohydride; toluene-4-sulfonic acid; pyridinium chlorochromate; trifluoroacetic acid; lithium chloride; In methanol; diethyl ether; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/ja00206a059

upstream raw materials:

(S)-9-(2-Hydroxy-1-hydroxymethyl-ethylamino)-8-methoxy-2,2-dimethyl-1,3-dioxa-spiro[4.5]dec-8-en-7-one

(1S,3R,4R,5R)-3,4-O-Benzylidene-1,3,4-trihydroxy-6-oxabicyclo<3.2.1>octan-7-one

D-(-)-quinic acid

(5S)-9-Azido-8-methoxy-2,2-dimethyl-1,3-dioxaspiro<4.5>dec-8-en-7-one

Refernces

• 1、 White,Cammack,Sakuma. "The synthesis and absolute configuration of mycosporins. A novel application of the Staudinger reaction". . p. 8970 - 8972. Retrieved 2007/10/02.