1-O-(5'-carbomethoxypentyl)-sn-glyceryl-3-tosylate

Base Information

• Chemical Name: 1-O-(5'-carbomethoxypentyl)-sn-glyceryl-3-tosylate
• CAS No.: 142350-40-1
• Molecular Formula: C₁₇H₂₆O₇S
• Molecular Weight: 374.455
• Mol file: 142350-40-1.mol

Synonyms:1-O-(5'-carbomethoxypentyl)-sn-glyceryl-3-tosylate

Chemical Property of 1-O-(5'-carbomethoxypentyl)-sn-glyceryl-3-tosylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-O-(5'-carbomethoxypentyl)-sn-glyceryl-3-tosylate

There total 3 articles about 1-O-(5'-carbomethoxypentyl)-sn-glyceryl-3-tosylate 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: 89.0%

methyl 6-hydroxycaproate (4547-43-7) + (R)-glycidyl tosylate (113826-06-5,6746-81-2) → 1-O-(5'-carbomethoxypentyl)-sn-glyceryl-3-tosylate (142350-40-1)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; for 4h; Ambient temperature;

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

Reference yield:

6-Hydroxyhexanoic acid (1191-25-9) → 1-O-(5'-carbomethoxypentyl)-sn-glyceryl-3-tosylate (142350-40-1)

Guidance literature:

Multi-step reaction with 2 steps

1: HCl

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

With hydrogenchloride; boron trifluoride diethyl etherate; In dichloromethane; 1: Esterification / 2: Ring cleavage;

DOI:10.1021/jo990739v

Reference yield:

6-Hydroxyhexanoic acid (1191-25-9) → 6-[(S)-2-Hydroxy-3-(toluene-4-sulfonyloxy)-propoxy]-hexanoic acid methyl ester (142350-40-1)

Guidance literature:

Multi-step reaction with 2 steps

1: HCl

2: BF₃*OEt₂ / CH₂Cl₂ / 4 h

With hydrogenchloride; boron trifluoride diethyl etherate; In dichloromethane; 1: Esterification / 2: Ring cleavage;

DOI:10.1021/jo990739v

upstream raw materials:

methyl 6-hydroxycaproate

(R)-glycidyl tosylate

6-Hydroxyhexanoic acid

Downstream raw materials:

1-O-(5'-carbomethoxypentyl)-2-tetrahydropyranyl-sn-3-glyceryl 2,2,2-trichloro-tert-butyl 1-N-triphenylmethylamino-1-carbomethoxy-2-propyl phosphate

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

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

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

Refernces

• 1、 Kazi, Abul B.,Shidmand, Sean,Hajdu, Joseph. "Stereospecific synthesis of functionalized ether phospholipids". . p. 9337 - 9347. Retrieved 2007/10/03.