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

Base Information

• Chemical Name: 1-O-(5'-carbomethoxypentyl)-2-tetrahydropyranyl-sn-glyceryl 2,2,2-trichloro-tert-butyl 2-carbomethoxy-2-(N-triphenylmethylamino)ethyl phosphite
• CAS No.: 257887-94-8
• Molecular Formula: C₄₂H₅₅Cl₃NO₁₀P
• Molecular Weight: 871.232
• Mol file: 257887-94-8.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 9 articles about 1-O-(5'-carbomethoxypentyl)-2-tetrahydropyranyl-sn-glyceryl 2,2,2-trichloro-tert-butyl 2-carbomethoxy-2-(N-triphenylmethylamino)ethyl phosphite 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: 69.0%

2,2,2-trichloro-1,1-dimethylethyldichloro phosphite (39177-74-7) + 1-O-(5'-carbomethoxypentyl)-2-tetrahydropyranyl-sn-glycerol (142350-43-4) + methyl N-trityl-L-serinate (13515-76-9,116457-91-1,4465-44-5) → 1-O-(5'-carbomethoxypentyl)-2-tetrahydropyranyl-sn-glyceryl 2,2,2-trichloro-tert-butyl 2-carbomethoxy-2-(N-triphenylmethylamino)ethyl phosphite (257887-94-8)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at -78 ℃;

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

Reference yield:

6-Hydroxyhexanoic acid (1191-25-9) → 1-O-(5'-carbomethoxypentyl)-2-tetrahydropyranyl-sn-glyceryl 2,2,2-trichloro-tert-butyl 2-carbomethoxy-2-(N-triphenylmethylamino)ethyl phosphite (257887-94-8)

Guidance literature:

Multi-step reaction with 6 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

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

DOI:10.1021/jo990739v

Reference yield:

methyl 6-hydroxycaproate (4547-43-7) → 1-O-(5'-carbomethoxypentyl)-2-tetrahydropyranyl-sn-glyceryl 2,2,2-trichloro-tert-butyl 2-carbomethoxy-2-(N-triphenylmethylamino)ethyl phosphite (257887-94-8)

Guidance literature:

Multi-step reaction with 5 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

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

DOI:10.1021/jo990739v

upstream raw materials:

2,2,2-trichloro-1,1-dimethylethyldichloro phosphite

1-O-(5'-carbomethoxypentyl)-2-tetrahydropyranyl-sn-glycerol

methyl N-trityl-L-serinate

3,4-dihydro-2H-pyran

Downstream raw materials:

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

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.