(2R,3R,4R,5S)-N⁽¹⁾-benzyl-2,5-bis(hydroxymethyl)-3-benzyloxy-4-hydroxypyrrolidine

Base Information

• Chemical Name: (2R,3R,4R,5S)-N⁽¹⁾-benzyl-2,5-bis(hydroxymethyl)-3-benzyloxy-4-hydroxypyrrolidine
• CAS No.: 1609168-89-9
• Molecular Formula: C₂₀H₂₅NO₄
• Molecular Weight: 343.423
• Mol file: 1609168-89-9.mol

Synonyms:(2R,3R,4R,5S)-N⁽¹⁾-benzyl-2,5-bis(hydroxymethyl)-3-benzyloxy-4-hydroxypyrrolidine

Chemical Property of (2R,3R,4R,5S)-N⁽¹⁾-benzyl-2,5-bis(hydroxymethyl)-3-benzyloxy-4-hydroxypyrrolidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R,4R,5S)-N⁽¹⁾-benzyl-2,5-bis(hydroxymethyl)-3-benzyloxy-4-hydroxypyrrolidine

There total 7 articles about (2R,3R,4R,5S)-N⁽¹⁾-benzyl-2,5-bis(hydroxymethyl)-3-benzyloxy-4-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: 100.0%

(2R,3R,4R,5S)-N(1)-benzyl-2,5-bis(acetoxymethyl)-3-benzyloxy-4-acetoxypyrrolidine (1609168-90-2) → (2R,3R,4R,5S)-N(1)-benzyl-2,5-bis(hydroxymethyl)-3-benzyloxy-4-hydroxypyrrolidine (1609168-89-9)

Guidance literature:

With potassium carbonate; In methanol; at 20 ℃; for 16h;

DOI:10.1016/j.tet.2014.03.100

Reference yield:

(1S,2R,3R,4R,5S)-N(1)-benzyl-2-[(triisopropylsilyloxy)methyl]-3-benzyloxy-4-hydroxy-1-azabicyclo[3.1.0]hexanium tetrafluoroborate → (2R,3R,4R,5S)-N(1)-benzyl-2,5-bis(hydroxymethyl)-3-benzyloxy-4-hydroxypyrrolidine (1609168-89-9) + (+)-(3R,4R,5R,6R)-1-benzyl-5-(benzyloxy)-6-(hydroxymethyl)piperidine-3,4-diol

Guidance literature:

(1S,2R,3R,4R,5S)-N⁽¹⁾-benzyl-2-[(triisopropylsilyloxy)methyl]-3-benzyloxy-4-hydroxy-1-azabicyclo[3.1.0]hexanium tetrafluoroborate; With water; In 1,4-dioxane; at 20 ℃; for 16h;

With pyridine; pyridine hydrogenfluoride; In tetrahydrofuran; at 0 - 20 ℃; for 16h;

DOI:10.1016/j.tet.2014.03.100

Reference yield:

(1S,2R,3R,4R,5S)-N(1)-benzyl-2-[(triisopropylsilyloxy)methyl]-3-benzyloxy-4-hydroxy-1-azabicyclo[3.1.0]hexanium tetrafluoroborate → (2R,3R,4R,5S)-N(1)-benzyl-2,5-bis(hydroxymethyl)-3-benzyloxy-4-hydroxypyrrolidine (1609168-89-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: water / 1,4-dioxane / 16 h / 20 °C

1.2: 16 h / 0 - 20 °C

1.3: 16 h / 0 - 20 °C

2.1: potassium carbonate / methanol / 16 h / 20 °C

With water; potassium carbonate; In 1,4-dioxane; methanol;

DOI:10.1016/j.tet.2014.03.100

upstream raw materials:

(2R,3R,4R,5S)-N⁽¹⁾-benzyl-2,5-bis(acetoxymethyl)-3-benzyloxy-4-acetoxypyrrolidine

(R,R,R,R)-4-benzyloxy-5-[N-benzyl-N-(α-methylbenzyl)amino]-6-(triisopropylsilyloxy)hex-1-en-3-ol

(R,R,R,R)-N⁽¹⁾-benzyl-2-[(triisopropylsilyloxy)methyl]-3-benzyloxy-4-hydroxy-5-(iodomethyl)pyrrolidine

Downstream raw materials:

(2R,3R,4R,5S)-N⁽¹⁾-benzyl-2,5-bis(hydroxymethyl)-3-benzyloxy-4-hydroxypyrrolidine hydrochloride

2,5-anhydro-2,5-imino-D-glucitol