1-O-(6-Carboxylhexyl)glycero-3-phosphoserine

Base Information

• Chemical Name: 1-O-(6-Carboxylhexyl)glycero-3-phosphoserine
• CAS No.: 139239-73-9
• Molecular Formula: C₁₃H₂₆NO₁₀P
• Molecular Weight: 387.324
• DSSTox Substance ID: DTXSID60160972
• Wikidata: Q83029332
• Mol file: 139239-73-9.mol

Synonyms:1-CHGPS;1-O-(6-carboxylhexyl)glycero-3-phosphoserine

Chemical Property of 1-O-(6-Carboxylhexyl)glycero-3-phosphoserine

Chemical Property:

• Vapor Pressure: 5.8E-20mmHg at 25°C
• Boiling Point: 655.5°Cat760mmHg
• Flash Point: 350.2°C
• PSA: 195.65000
• Density: 1.408g/cm³
• LogP: 0.64480
• XLogP3: -4.3
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 16
• Exact Mass: 387.12943302
• Heavy Atom Count: 25
• Complexity: 447

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C(CCCOCC(COP(=O)(O)OCC(C(=O)O)N)O)CCC(=O)O
• Isomeric SMILES: C(CCCOC[C@H](COP(=O)(O)OC[C@@H](C(=O)O)N)O)CCC(=O)O

Technology Process of 1-O-(6-Carboxylhexyl)glycero-3-phosphoserine

There total 10 articles about 1-O-(6-Carboxylhexyl)glycero-3-phosphoserine 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: 80.0%

7-{(R)-3-[((S)-2-Benzylamino-2-benzyloxycarbonyl-ethoxy)-hydroxy-phosphoryloxy]-2-benzyloxy-propoxy}-heptanoic acid benzyl ester → 1-O-(6-Carboxyhexyl)-sn-glycero-3-phosphoserine (139239-73-9)

Guidance literature:

With hydrogen; palladium dihydroxide; pyrographite; In methanol; water; for 18h; under 760 Torr; Ambient temperature;

DOI:10.1016/S0040-4020(01)96051-X

Reference yield:

ethyl 7-bromoheptanoate (29823-18-5) → 1-O-(6-Carboxyhexyl)-sn-glycero-3-phosphoserine (139239-73-9)

Guidance literature:

Multi-step reaction with 10 steps

1: 1) NaH / 1) DMF, rt, 2.5 h, 2) DMF, rt, 48 h

2: 10.4 g / 1.6 M NaOH / dioxane / 18 h / Ambient temperature

3: NaHCO₃ / dimethylformamide / 18 h / 40 °C

4: 82 percent / 2 M HCl / tetrahydrofuran / 4 h / Ambient temperature

5: 80 percent / pyridine / 17 h / Ambient temperature

6: 1) NaH, 2) BuN₄I / 1) DMF, 45 min, rt, 2) DMF, 24 h, rt

7: 55 percent / 1 M HCl / dioxane / 4 h / 80 °C

8: 1) imidazole, PCl₃, Et₃N / 1) MeCN, 15 min, 2) MeCN, toluene, rt, 4 h

9: I₂ / H₂O; pyridine / 0.5 h / Ambient temperature

10: 80 percent / H₂ / 20percent Pd(OH)2/charcoal / methanol; H₂O / 18 h / 760 Torr / Ambient temperature

With pyridine; 1H-imidazole; hydrogenchloride; sodium hydroxide; hydrogen; iodine; tetra-(n-butyl)ammonium iodide; sodium hydride; sodium hydrogencarbonate; triethylamine; phosphorus trichloride; palladium dihydroxide; pyrographite; In tetrahydrofuran; 1,4-dioxane; pyridine; methanol; water; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(01)96051-X

Reference yield:

1-O-<6-(Benzyloxycarbonyl)hexyl>-2-O-benzyl-sn-glycero-3H-phosphonic acid triethylammonium salt (139141-25-6) → 1-O-(6-Carboxyhexyl)-sn-glycero-3-phosphoserine (139239-73-9)

Guidance literature:

Multi-step reaction with 2 steps

1: I₂ / H₂O; pyridine / 0.5 h / Ambient temperature

2: 80 percent / H₂ / 20percent Pd(OH)2/charcoal / methanol; H₂O / 18 h / 760 Torr / Ambient temperature

With hydrogen; iodine; palladium dihydroxide; pyrographite; In pyridine; methanol; water;

DOI:10.1016/S0040-4020(01)96051-X

upstream raw materials:

ethyl 7-bromoheptanoate

1-O-<6-(Benzyloxycarbonyl)hexyl>-2-O-benzyl-sn-glycero-3H-phosphonic acid triethylammonium salt

1-O-(6-Carboxyhexyl)-2,3-isopropylidene-sn-glycerol

1-O-(6-Ethoxycarbonylhexyl)-2,3-isopropylidene-sn-glycerol