[S-(R*,R*)]-[2-Hydroxy-1-[(methoxyamino)carbonyl]propyl]-carbamic Acid 1,1-Dimethylethyl Ester

Base Information

• Chemical Name: [S-(R*,R*)]-[2-Hydroxy-1-[(methoxyamino)carbonyl]propyl]-carbamic Acid 1,1-Dimethylethyl Ester
• CAS No.: 80543-39-1
• Molecular Formula: C₁₀H₂₀N₂O₅
• Molecular Weight: 248.279
• DSSTox Substance ID: DTXSID00595082
• Wikidata: Q82490021
• Mol file: 80543-39-1.mol

Synonyms:80543-39-1;[S-(R*,R*)]-[2-Hydroxy-1-[(methoxyamino)carbonyl]propyl]-carbamic Acid 1,1-Dimethylethyl Ester;Tert-butyl N-[(2S,3S)-3-hydroxy-1-(methoxyamino)-1-oxobutan-2-yl]carbamate;tert-Butyl ((2S,3S)-3-hydroxy-1-(methoxyamino)-1-oxobutan-2-yl)carbamate;starbld0003662;DTXSID00595082;N~2~-(tert-Butoxycarbonyl)-N-methoxy-L-allothreoninamide

Chemical Property of [S-(R*,R*)]-[2-Hydroxy-1-[(methoxyamino)carbonyl]propyl]-carbamic Acid 1,1-Dimethylethyl Ester

Chemical Property:

• PKA: 11.05±0.46(Predicted)
• PSA: 103.87000
• Density: 1.146±0.06 g/cm3(Predicted)
• LogP: 0.98280
• Solubility.: Dichloromethane, Methanol
• XLogP3: 0.1
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 6
• Exact Mass: 248.13722174
• Heavy Atom Count: 17
• Complexity: 274

Purity/Quality:

[S-(R*,R*)]-[2-Hydroxy-1-[(methoxyamino)carbonyl]propyl]-carbamicAcid1,1-DimethylethylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C(C(=O)NOC)NC(=O)OC(C)(C)C)O
• Isomeric SMILES: C[C@@H]([C@@H](C(=O)NOC)NC(=O)OC(C)(C)C)O
• Uses: [S-(R*,R*)]-[2-Hydroxy-1-[(methoxyamino)carbonyl]propyl]-carbamic Acid 1,1-Dimethylethyl Ester (cas# 80543-39-1) is a compound useful in organic synthesis.

Technology Process of [S-(R*,R*)]-[2-Hydroxy-1-[(methoxyamino)carbonyl]propyl]-carbamic Acid 1,1-Dimethylethyl Ester

There total 3 articles about [S-(R*,R*)]-[2-Hydroxy-1-[(methoxyamino)carbonyl]propyl]-carbamic Acid 1,1-Dimethylethyl Ester 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:

di-tert-butyl dicarbonate (24424-99-5) → ((1S,2S)-2-Hydroxy-1-methoxycarbamoyl-propyl)-carbamic acid tert-butyl ester (80543-39-1)

Guidance literature:

Multi-step reaction with 2 steps

1: aq. KOH; 2-methyl-propan-2-ol / 5 h

2: 1-ethyl-3-<3-(dimethylamino)propyl>carbodiimide (WSC) / pH=4.2

With N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In potassium hydroxide; tert-butyl alcohol;

DOI:10.1021/jo00147a024

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) + (2S,3S)-2-Azido-3-hydroxy-N-methoxy-butyramide → ((1S,2S)-2-Hydroxy-1-methoxycarbamoyl-propyl)-carbamic acid tert-butyl ester (80543-39-1)

Guidance literature:

With hydrogen; palladium on activated charcoal; Yield given. Multistep reaction;

DOI:10.1016/S0040-4039(00)95643-0

Reference yield:

N-tert-butoxycarbonyl-L-allo-threonine (2592-18-9,23082-29-3,55674-67-4,85979-33-5,86748-77-8,23082-30-6) + N-methoxylamine hydrochloride (593-56-6) → ((1S,2S)-2-Hydroxy-1-methoxycarbamoyl-propyl)-carbamic acid tert-butyl ester (80543-39-1)

Guidance literature:

With N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; Yield given; pH=4.2;

DOI:10.1021/jo00147a024

upstream raw materials:

di-tert-butyl dicarbonate

N-tert-butoxycarbonyl-L-allo-threonine

N-methoxylamine hydrochloride

Downstream raw materials:

Methanesulfonic acid (1S,2S)-2-tert-butoxycarbonylamino-2-methoxycarbamoyl-1-methyl-ethyl ester