(2R)-3-(tert-butylamino)propane-1,2-diol

Base Information

• Chemical Name: (2R)-3-(tert-butylamino)propane-1,2-diol
• CAS No.: 59207-70-4
• Molecular Formula: C7H17NO2
• Molecular Weight: 147.217
• UNII: VV6W84D5I4
• Nikkaji Number: J1.371.386C
• Mol file: 59207-70-4.mol

Synonyms:59207-70-4;(2R)-3-(tert-butylamino)propane-1,2-diol;(R)-3-(tert-Butylamino)propane-1,2-diol;VV6W84D5I4;1-tert-Butylamino-2,3-propanediol, (+)-;1-tert-Butylamino-2,3-propanediol, (R)-;1,2-Propanediol, 3-((1,1-dimethylethyl)amino)-, (2R)-;(S)-3-tert-Butylamino-propane-1,2-diol;UNII-VV6W84D5I4;SCHEMBL5878869;MFCD00236894;AKOS006273929;AM806406;BS-41776;(R)-3-(tert-Butylamino)-1,2-propanediol;(S)-(-)-tert-Butylamino-1,2-propanediol;CS-0047365

Chemical Property of (2R)-3-(tert-butylamino)propane-1,2-diol

Chemical Property:

• PSA: 52.49000
• LogP: 0.11860
• XLogP3: -0.5
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 147.125928785
• Heavy Atom Count: 10
• Complexity: 88.1

Purity/Quality:

99% ^*data from raw suppliers

(2R)?-?3-?(tert-?Butylamino)?propane-?1,?2-?diol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(C)(C)NCC(CO)O
• Isomeric SMILES: CC(C)(C)NC[C@H](CO)O
• Uses: (2R)?-?3-?(tert-?Butylamino)?propane-?1,?2-?diol is an organic reagent used in pharmaceutical synthesis. (2R)?-?3-?(tert-?Butylamino)?propane-?1,?2-?diol is a reagent in the biological resolution of racemic 2-oxazolidinones.

Technology Process of (2R)-3-(tert-butylamino)propane-1,2-diol

There total 3 articles about (2R)-3-(tert-butylamino)propane-1,2-diol 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: 93.0%

(R)-5-hydroxymethyl-3-tert-butyl-2-oxazolodinone (98048-84-1) → (R)-1-tert-butylamino-2,3-dihydroxypropane (59207-70-4)

Guidance literature:

With sodium hydroxide; water; at 95 ℃; for 15h;

DOI:10.1271/bbb1961.49.1669

Reference yield:

tert-butylamine (75-64-9) + (S)-oxiranemethanol (60456-23-7) → (R)-1-tert-butylamino-2,3-dihydroxypropane (59207-70-4)

Guidance literature:

In water; Yield given; Heating;

DOI:10.1021/jo00086a052

Reference yield:

(R,S)-5-hexanoyloxymethyl-3-tert-butyl-oxazolidin-2-one → (R)-1-tert-butylamino-2,3-dihydroxypropane (59207-70-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 40 percent / lipoprotein lipase Amano 3 adsorbed on Amberlite XAD-7, H₂O / 6 h / 33 °C / pH = 7.0

2: 93 percent / NaOH, H₂O / 15 h / 95 °C

With sodium hydroxide; lipoprotein lipase Amano 3 adsorbed on Amberlite XAD-7; water;

DOI:10.1271/bbb1961.49.1669

upstream raw materials:

(R)-5-hydroxymethyl-3-tert-butyl-2-oxazolodinone

tert-butylamine

(S)-oxiranemethanol

Downstream raw materials:

(R)-2-phenyl-3-tert-butyl-5-(hydroxymethyl)oxazolidine

(S)-glyceraldehyde

(R)-3-tert-butylamino-1,2-epoxypropane

Refernces

• 1、 Kan,Miyama,Hamaguchi,et al.. "Stereochemical inversion of (R)-5-hydroxymethyl-3-tert-butyl-2-oxazolidinone or (R)-5-hydroxymethyl-3-isopropyl-2-oxazolidinone to the corresponding (S)-isomer". . p. 1669 - 1674. Retrieved 2007/10/02.