1-O-(5'-carbomethoxypentyl)-2-tetrahydropyranyl-sn-3-glyceroyl 2,2,2-trichloro-tert-butyl 2-N-tritylamino-2-carbomethoxyethyl phosphate

Base Information

• Chemical Name: 1-O-(5'-carbomethoxypentyl)-2-tetrahydropyranyl-sn-3-glyceroyl 2,2,2-trichloro-tert-butyl 2-N-tritylamino-2-carbomethoxyethyl phosphate
• CAS No.: 142350-44-5
• Molecular Formula: C₄₂H₅₅Cl₃NO₁₁P
• Molecular Weight: 887.232
• Mol file: 142350-44-5.mol

Synonyms:1-O-(5'-carbomethoxypentyl)-2-tetrahydropyranyl-sn-3-glyceroyl 2,2,2-trichloro-tert-butyl 2-N-tritylamino-2-carbomethoxyethyl phosphate

Chemical Property of 1-O-(5'-carbomethoxypentyl)-2-tetrahydropyranyl-sn-3-glyceroyl 2,2,2-trichloro-tert-butyl 2-N-tritylamino-2-carbomethoxyethyl phosphate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-O-(5'-carbomethoxypentyl)-2-tetrahydropyranyl-sn-3-glyceroyl 2,2,2-trichloro-tert-butyl 2-N-tritylamino-2-carbomethoxyethyl phosphate

There total 11 articles about 1-O-(5'-carbomethoxypentyl)-2-tetrahydropyranyl-sn-3-glyceroyl 2,2,2-trichloro-tert-butyl 2-N-tritylamino-2-carbomethoxyethyl phosphate 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: 95.0%

1-O-(5'-carbomethoxypentyl)-2-tetrahydropyranyl-sn-glyceryl 2,2,2-trichloro-tert-butyl 2-carbomethoxy-2-(N-triphenylmethylamino)ethyl phosphite (257887-94-8) → 1-O-(5'-carbomethoxypentyl)-2-tetrahydropyranyl-sn-3-glyceroyl 2,2,2-trichloro-tert-butyl 2-N-tritylamino-2-carbomethoxyethyl phosphate (142350-44-5)

Guidance literature:

With dihydrogen peroxide; In dichloromethane; for 2h; Ambient temperature;

DOI:10.1016/S0040-4039(00)74193-1

Reference yield:

6-Hydroxyhexanoic acid (1191-25-9) → 1-O-(5'-carbomethoxypentyl)-2-tetrahydropyranyl-sn-3-glyceroyl 2,2,2-trichloro-tert-butyl 2-N-tritylamino-2-carbomethoxyethyl phosphate (142350-44-5)

Guidance literature:

Multi-step reaction with 7 steps

1: HCl

2: 89 percent / BF₃*OEt₂ / CH₂Cl₂ / 4 h

3: 69 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 4 h / 20 °C

4: 90 percent / molecular sieves 3A / acetonitrile / 36 h / 20 °C

5: 75 percent / potassium carbonate / methanol / 0.5 h / 0 °C

6: 69 percent / diisopropylethylamine / tetrahydrofuran / -78 - 20 °C

7: 95 percent / hydrogen peroxide / H₂O; CH₂Cl₂ / 2 h / 20 °C

With hydrogenchloride; 3 A molecular sieve; boron trifluoride diethyl etherate; dihydrogen peroxide; pyridinium p-toluenesulfonate; potassium carbonate; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; dichloromethane; water; acetonitrile; 1: Esterification / 2: Ring cleavage / 3: Addition / 4: Acetoxylation / 5: Deacetylation / 6: coupling; phosphitylation; phosphorylation / 7: Oxidation;

DOI:10.1021/jo990739v

Reference yield:

methyl 6-hydroxycaproate (4547-43-7) → 1-O-(5'-carbomethoxypentyl)-2-tetrahydropyranyl-sn-3-glyceroyl 2,2,2-trichloro-tert-butyl 2-N-tritylamino-2-carbomethoxyethyl phosphate (142350-44-5)

Guidance literature:

Multi-step reaction with 6 steps

1: 89 percent / BF₃*OEt₂ / CH₂Cl₂ / 4 h

2: 69 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 4 h / 20 °C

3: 90 percent / molecular sieves 3A / acetonitrile / 36 h / 20 °C

4: 75 percent / potassium carbonate / methanol / 0.5 h / 0 °C

5: 69 percent / diisopropylethylamine / tetrahydrofuran / -78 - 20 °C

6: 95 percent / hydrogen peroxide / H₂O; CH₂Cl₂ / 2 h / 20 °C

With 3 A molecular sieve; boron trifluoride diethyl etherate; dihydrogen peroxide; pyridinium p-toluenesulfonate; potassium carbonate; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; dichloromethane; water; acetonitrile; 1: Ring cleavage / 2: Addition / 3: Acetoxylation / 4: Deacetylation / 5: coupling; phosphitylation; phosphorylation / 6: Oxidation;

DOI:10.1021/jo990739v

upstream raw materials:

1-O-(5'-carbomethoxypentyl)-2-tetrahydropyranyl-sn-glyceryl 2,2,2-trichloro-tert-butyl 2-carbomethoxy-2-(N-triphenylmethylamino)ethyl phosphite

3,4-dihydro-2H-pyran

6-Hydroxyhexanoic acid

methyl 6-hydroxycaproate

Refernces

• 1、 Kazi, Abul B.,Hajdu, Joseph. "Synthesis of Phosphoserine and Phosphothreonine Ether-Glycerolipids via 2,2,2-Trichloro-t-Butyl Phosphodichloridite Coupling". . p. 2291 - 2294. Retrieved 2007/10/02.