(1R,2R)-B13

Base Information

• Chemical Name: (1R,2R)-B13
• CAS No.: 35922-06-6
• Molecular Formula: C₂₃H₃₈N₂O₅
• Molecular Weight: 422.565
• Mol file: 35922-06-6.mol

Synonyms:Tetradecanamide,N-[2-hydroxy-1-(hydroxymethyl)-2-(4-nitrophenyl)ethyl]-, [R-(R*,R*)]-

Chemical Property of (1R,2R)-B13

Chemical Property:

• PSA: 115.38000
• LogP: 5.72050

Purity/Quality:

99% ^*data from raw suppliers

D-NMAPPD ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: D-NMAPPD is d-NMAPPD is a potent Acid Ceramidase inhibitor that induces apoptosis..

Technology Process of (1R,2R)-B13

There total 3 articles about (1R,2R)-B13 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: 61.4%

N-((1S,2R)-1-hydroxyl-1-(4-nitrophenyl)-3-(trityloxy)propan-2-yl)tetra-decanamide → N-((1S,2R)-1,3-dihydroxy-1-(4′-nitrophenyl)-propan-2-yl)tetradecanamide (35922-06-6)

Guidance literature:

With acetic acid; at 20 ℃;

DOI:10.1016/j.bmc.2021.116011

Reference yield:

N-((1R,2R)-1-hydroxy-1-(4-nitrophenyl)-3-(trityloxy)propan-2-yl)tetra-decanamide → N-((1S,2R)-1,3-dihydroxy-1-(4′-nitrophenyl)-propan-2-yl)tetradecanamide (35922-06-6)

Guidance literature:

Multi-step reaction with 3 steps

1: pyridinium chlorochromate / dichloromethane / 4 - 20 °C

2: sodium tetrahydroborate; methanol / dichloromethane / 4 - 20 °C

3: acetic acid / 20 °C

With methanol; sodium tetrahydroborate; acetic acid; pyridinium chlorochromate; In dichloromethane;

DOI:10.1016/j.bmc.2021.116011

Reference yield:

(1R,2R)-2-N-(tetradecanoylamino)-1-(4'-nitrophenyl)-1,3-propandiol (35922-06-6) → N-((1S,2R)-1,3-dihydroxy-1-(4′-nitrophenyl)-propan-2-yl)tetradecanamide (35922-06-6)

Guidance literature:

Multi-step reaction with 4 steps

1: dmap; triethylamine / dichloromethane / 20 °C

2: pyridinium chlorochromate / dichloromethane / 4 - 20 °C

3: sodium tetrahydroborate; methanol / dichloromethane / 4 - 20 °C

4: acetic acid / 20 °C

With methanol; dmap; sodium tetrahydroborate; acetic acid; triethylamine; pyridinium chlorochromate; In dichloromethane;

DOI:10.1016/j.bmc.2021.116011

Downstream raw materials:

(1R,2R)-2-N-(tetradecanoylamino)-1-hydroxy-1-(4'-nitrophenyl)propyl-3-O-(N,N-dimethylamino)acetate hydrochloride

(1R,2R)-2-N-(tetradecanoylamino)-1-(4'-nitrophenyl)-3-hydroxypropyl-1-O-(N,N-dimethylamino)acetate

Refernces