tert-butyl (2R,5S)-2-(benzyloxymethyl)-5,6-dihydro-5-hydroxypyridine-1(2H)-carboxylate

Base Information

• Chemical Name: tert-butyl (2R,5S)-2-(benzyloxymethyl)-5,6-dihydro-5-hydroxypyridine-1(2H)-carboxylate
• CAS No.: 1393105-88-8
• Molecular Formula: C₁₈H₂₅NO₄
• Molecular Weight: 319.401
• Mol file: 1393105-88-8.mol

Synonyms:tert-butyl (2R,5S)-2-(benzyloxymethyl)-5,6-dihydro-5-hydroxypyridine-1(2H)-carboxylate

Chemical Property of tert-butyl (2R,5S)-2-(benzyloxymethyl)-5,6-dihydro-5-hydroxypyridine-1(2H)-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl (2R,5S)-2-(benzyloxymethyl)-5,6-dihydro-5-hydroxypyridine-1(2H)-carboxylate

There total 15 articles about tert-butyl (2R,5S)-2-(benzyloxymethyl)-5,6-dihydro-5-hydroxypyridine-1(2H)-carboxylate 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%

tert-butyl (2R,5S)-5-(benzoyloxy)-2-(benzyloxymethyl)-5,6-dihydropyridine-1(2H)-carboxylate → tert-butyl (2R,5S)-2-(benzyloxymethyl)-5,6-dihydro-5-hydroxypyridine-1(2H)-carboxylate (1393105-88-8)

Guidance literature:

With water; sodium hydroxide; In methanol; at 0 - 20 ℃; for 3h; Inert atmosphere;

DOI:10.1002/ejoc.201200377

Reference yield: 35.0%

tert-butyl (R)-6-((benzyloxy)methyl)-3,6-dihydropyridine-1(2H)-carboxylate → tert-butyl (2R,5S)-2-(benzyloxymethyl)-5,6-dihydro-5-hydroxypyridine-1(2H)-carboxylate (1393105-88-8)

Guidance literature:

With selenium(IV) oxide; In 1,4-dioxane; for 3h; stereoselective reaction; Reflux;

DOI:10.1039/c4ra04558k

Reference yield:

C13H19NO2 → tert-butyl (2R,5S)-2-(benzyloxymethyl)-5,6-dihydro-5-hydroxypyridine-1(2H)-carboxylate (1393105-88-8)

Guidance literature:

Multi-step reaction with 3 steps

1: triethylamine; dmap / tetrahydrofuran / 20 °C

2: triphenylphosphine; 1H-imidazole; iodine / toluene / 0.5 h / 120 °C / Inert atmosphere

3: selenium(IV) oxide / 1,4-dioxane / 3 h / Reflux

With 1H-imidazole; dmap; selenium(IV) oxide; iodine; triethylamine; triphenylphosphine; In tetrahydrofuran; 1,4-dioxane; toluene;

DOI:10.1039/c4ra04558k

upstream raw materials:

(R,E)-N-((R)-1-(benzyloxy)but-3-en-2-yl)-2-(tert-butyldiphenylsilyloxy)pent-3-en-1-amine

tert-butyl (R)-1-(benzyloxy)but-3-en-2-yl((R,E)-2-(tert-butyldiphenylsilyloxy)pent-3-enyl)carbamate

tert-butyl (3R,6R)-6-((benzyloxy)methyl)-3-((tert-butyldiphenylsilyl)oxy)-3,6-dihydropyridine-1(2H)-carboxylate

tert-butyl (2R,5R)-2-(benzyloxymethyl)-5,6-dihydro-5-hydroxypyridine-1(2H)-carboxylate

Downstream raw materials:

tert-butyl (2S,3S,4R,5R)-2-(benzyloxymethyl)-3,4,5-trihydroxypiperidine-1-carboxylate

tert-butyl (2S,3R,4S,5R)-2-(benzyloxymethyl)-3,4,5-trihydroxypiperidine-1-carboxylate

tert-butyl 2-(benzyloxymethyl)-5-(tert-butyldiphenylsilyloxy)-3,4-dihydroxypiperidine-1-carboxylate

C₂₁H₃₁NO₆