2-amino-6-[(1S,2R)-1,2-dihydroxypropyl]-4(1H)-Pteridinone

Base Information

• Chemical Name: 2-amino-6-[(1S,2R)-1,2-dihydroxypropyl]-4(1H)-Pteridinone
• CAS No.: 13039-62-8
• Molecular Formula: C9H11 N5 O3
• Molecular Weight: 237.22
• Hs Code.: 2933990090
• Mol file: 13039-62-8.mol

Synonyms:1,2-Propanediol,1-(2-amino-4-hydroxy-6-pteridinyl)-, D-erythro- (8CI); 4(1H)-Pteridinone, 2-amino-6-(1,2-dihydroxypropyl)-,[R-(R*,S*)]-; (1'S,2'R)-Biopterin; D-6-(erythro-1,2-Dihydroxypropyl)pterin;D-Biopterin; D-erythro-Biopterin

Chemical Property of 2-amino-6-[(1S,2R)-1,2-dihydroxypropyl]-4(1H)-Pteridinone

Chemical Property:

• Vapor Pressure: 8.98E-15mmHg at 25°C
• Refractive Index: 1.821
• Boiling Point: 590.2°Cat760mmHg
• Flash Point: 310.7°C
• PSA: 138.01000
• Density: 1.86g/cm³
• LogP: -0.70930

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: D-Biopterin is a biologically active pteridine. A pigment in the dorsal skin of frogs.

Technology Process of 2-amino-6-[(1S,2R)-1,2-dihydroxypropyl]-4(1H)-Pteridinone

There total 8 articles about 2-amino-6-[(1S,2R)-1,2-dihydroxypropyl]-4(1H)-Pteridinone 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: 92.0%

(3S,8S,9S,10R,13S,14S,17S)-3-Acetoxy-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-17-carboxylic acid (1R,2S)-2-(2-amino-4-butoxy-pteridin-6-yl)-2-hydroxy-1-methyl-ethyl ester (141191-98-2,141271-04-7) → D-erythro-biopterin (13039-62-8)

Guidance literature:

With potassium hydroxide; In methanol; at 100 ℃; for 1h;

DOI:10.1055/s-1992-26097

Reference yield: 15.7%

(1'R,2'S,6R)-2-amino-6-(1',2'-dihydroxypropyl)-5,6,7,8-tetrahydropterin-4(3H)-one-dihydrochloride (62989-33-7) → 7,8-dihydrobiopterin (1262750-77-5) + D-erythro-biopterin (13039-62-8)

Guidance literature:

With oxygen; In aq. acetate buffer; at 25 ℃; for 1h; pH=7.2;

DOI:10.1016/j.jphotochem.2017.07.029

Reference yield:

5-<(Tetrahydro-2H-pyran-2-yl)oxy>-3-pentyn-2-ol (14092-30-9) → D-erythro-biopterin (13039-62-8)

Guidance literature:

Multi-step reaction with 7 steps

1: pyridine / 1 h / 20 °C

2: pyridinium p-toluenesulfonate / methanol / 20 h / 20 °C

3: H₂ / Lindlar catalyst, quinoline / benzene / 0.17 h / 20 °C

4: MnO₂ / CH₂Cl₂ / 27 h / 20 °C

5: 35percent H₂O₂, NaHCO₃ / methanol / 2 h / 0 °C

6: 2.) I₂, HCO₂H / 1.) MeOH, 20 deg C, 16 h, 2.) 1 h

7: 92 percent / 0.1 M KOH / methanol / 1 h / 100 °C

With pyridine; manganese(IV) oxide; potassium hydroxide; formic acid; hydrogen; dihydrogen peroxide; iodine; pyridinium p-toluenesulfonate; sodium hydrogencarbonate; quinoline; Lindlar's catalyst; In methanol; dichloromethane; benzene;

DOI:10.1055/s-1992-26097

upstream raw materials:

(3S,8S,9S,10R,13S,14S,17S)-3-Acetoxy-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-17-carboxylic acid (1R,2S)-2-(2-amino-4-butoxy-pteridin-6-yl)-2-hydroxy-1-methyl-ethyl ester

5-<(Tetrahydro-2H-pyran-2-yl)oxy>-3-pentyn-2-ol

(3S,8S,9S,10R,13S,14S,17S)-3-Acetoxy-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-17-carboxylic acid 1-methyl-4-(tetrahydro-pyran-2-yloxy)-but-2-ynyl ester

(3S,8S,9S,10R,13S,14S,17S)-3-Acetoxy-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-17-carboxylic acid (Z)-(R)-4-hydroxy-1-methyl-but-2-enyl ester

Refernces

• 1、 Murata,Sugimoto,Ogiwara,Mogi,Wasada. "Novel regio- and stereoselective synthesis of 6-substituted pteridines and naturally occurring L-erythro-biopterin". . p. 303 - 308. Retrieved 2007/10/02.