(2R,3R,4R)-3,4-bis(benzyloxy)-2-benzyloxymethyl-N-hydroxypyrrolidine

Base Information

• Chemical Name: (2R,3R,4R)-3,4-bis(benzyloxy)-2-benzyloxymethyl-N-hydroxypyrrolidine
• CAS No.: 960040-52-2
• Molecular Formula: C₂₆H₂₉NO₄
• Molecular Weight: 419.521
• Mol file: 960040-52-2.mol

Synonyms:(2R,3R,4R)-3,4-bis(benzyloxy)-2-benzyloxymethyl-N-hydroxypyrrolidine

Chemical Property of (2R,3R,4R)-3,4-bis(benzyloxy)-2-benzyloxymethyl-N-hydroxypyrrolidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R,4R)-3,4-bis(benzyloxy)-2-benzyloxymethyl-N-hydroxypyrrolidine

There total 4 articles about (2R,3R,4R)-3,4-bis(benzyloxy)-2-benzyloxymethyl-N-hydroxypyrrolidine 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: 83.0%

(2R,3R,4R)-3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-3,4-dihydro-2H-pyrrole 1-oxide (537030-19-6) → (2R,3R,4R)-3,4-bis(benzyloxy)-2-benzyloxymethyl-N-hydroxypyrrolidine (960040-52-2)

Guidance literature:

With sodium tetrahydroborate; In ethanol; at 20 ℃; for 18h;

DOI:10.1021/acs.orglett.5b02029

Reference yield: 73.0%

(2R,3S,4S)-2,3,5-tri(benzyloxy)-1,4-di(methylsulfonyloxy)pentane (135910-18-8) → (2R,3R,4R)-3,4-bis(benzyloxy)-2-benzyloxymethyl-N-hydroxypyrrolidine (960040-52-2)

Guidance literature:

With hydroxylamine hydrochloride; triethylamine; for 14h; Reflux;

DOI:10.1021/acs.orglett.5b02029

Reference yield:

2,3,5-tri-O-benzyl-L-xylofuranose (16838-89-4,17073-88-0,60933-68-8,60933-69-9,73068-66-3,89361-52-4,89615-42-9,89615-45-2,96192-07-3) → (2R,3R,4R)-3,4-bis(benzyloxy)-2-benzyloxymethyl-N-hydroxypyrrolidine (960040-52-2)

Guidance literature:

Multi-step reaction with 3 steps

1: sodium tetrahydroborate / ethanol / 0 - 20 °C

2: pyridine / 0 - 20 °C / Inert atmosphere

3: triethylamine; hydroxylamine hydrochloride / 14 h / Reflux

With pyridine; sodium tetrahydroborate; hydroxylamine hydrochloride; triethylamine; In ethanol;

DOI:10.1021/acs.orglett.5b02029

upstream raw materials:

(2R,3R,4R)-3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-3,4-dihydro-2H-pyrrole 1-oxide

2,3,5-tri-O-benzyl-L-xylofuranose

(3R,4R,5R)-3,4,6-tris(benzyloxy)hexane-1,5-diol

(2R,3S,4S)-2,3,5-tri(benzyloxy)-1,4-di(methylsulfonyloxy)pentane

Downstream raw materials:

(2R,3R,4R)-3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-3,4-dihydro-2H-pyrrole 1-oxide

(2R,3R,4R)-3,4-Dibenzyloxy-2-(benzyloxymethyl)pyrrolidine