(2R,6R)-N-Tosyl-6-ethoxy-2-methoxymethyl-1,2,3,6-tetrahydropyridin-3-one

Base Information

• Chemical Name: (2R,6R)-N-Tosyl-6-ethoxy-2-methoxymethyl-1,2,3,6-tetrahydropyridin-3-one
• CAS No.: 176209-09-9
• Molecular Formula: C₁₆H₂₁NO₅S
• Molecular Weight: 339.412
• Mol file: 176209-09-9.mol

Synonyms:(2R,6R)-N-Tosyl-6-ethoxy-2-methoxymethyl-1,2,3,6-tetrahydropyridin-3-one

Chemical Property of (2R,6R)-N-Tosyl-6-ethoxy-2-methoxymethyl-1,2,3,6-tetrahydropyridin-3-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,6R)-N-Tosyl-6-ethoxy-2-methoxymethyl-1,2,3,6-tetrahydropyridin-3-one

There total 2 articles about (2R,6R)-N-Tosyl-6-ethoxy-2-methoxymethyl-1,2,3,6-tetrahydropyridin-3-one 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: 76.5%

orthoformic acid triethyl ester (122-51-0) + (2R,6R)-N-Tosyl-6-hydroxy-2-methoxymethyl-1,2,3,6-tetrahydropyridin-3-one (176209-08-8) → (2R,6R)-N-Tosyl-6-ethoxy-2-methoxymethyl-1,2,3,6-tetrahydropyridin-3-one (176209-09-9)

Guidance literature:

With boron trifluoride diethyl etherate; In tetrahydrofuran; at 0 ℃;

DOI:10.1016/0040-4039(96)00041-X

Reference yield:

1-(2-Furyl)-2-methoxy-N-tosylethylamine (176209-07-7) → (2R,6R)-N-Tosyl-6-ethoxy-2-methoxymethyl-1,2,3,6-tetrahydropyridin-3-one (176209-09-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 42.7 percent / Ti(O-i-Pr)4, L-(+)-DIPT, TBHP, CaH₂, silica gel / CH₂Cl₂ / 72 h / Ambient temperature

2: 76.5 percent / BF₃*OEt₂, MS 4A / tetrahydrofuran / 3 h / 0 °C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; calcium hydride; L-(+)-diisopropyl tartrate; boron trifluoride diethyl etherate; silica gel; In tetrahydrofuran; dichloromethane;

DOI:10.1039/a605128f

Reference yield: 72.3%

(2R,6R)-N-Tosyl-6-ethoxy-2-methoxymethyl-1,2,3,6-tetrahydropyridin-3-one (176209-09-9) → (2R,3R,6R)-1-Tosyl-6-ethoxy-2-methoxymethyl-1,2,3,6-tetrahydropyridin-3-ol (176209-10-2)

Guidance literature:

With sodium tetrahydroborate; cerium(III) chloride; at -30 ℃;

DOI:10.1016/0040-4039(96)00041-X

upstream raw materials:

orthoformic acid triethyl ester

(2R,6R)-N-Tosyl-6-hydroxy-2-methoxymethyl-1,2,3,6-tetrahydropyridin-3-one

1-(2-Furyl)-2-methoxy-N-tosylethylamine

Downstream raw materials:

(2R,3R,6R)-1-Tosyl-6-ethoxy-2-methoxymethyl-1,2,3,6-tetrahydropyridin-3-ol

1-deoxymannojirimycin

(2R,3S)-1-Tosyl-2-methoxymethyl-1,2,3,6-tetrahydro-3-pyridyl benzoate

(2R,3S,4R,5R)-1-Tosyl-4,5-dihydroxy-2-methoxymethyl-3-piperidyl benzoate