Boc-(rs)-3-amino-1,2-propanediol

• CAS: 137618-48-5
• Catalog Number: ACM137618485
• Category: Main Products
• Molecular Weight: 191.22
• Molecular Formula: C₈H₁₇NO₄
• Synonyms: TERT-BUTYL N-(2,3-DIHYDROXYPROPYL)CARBAMATE;BOC-(RS)-3-AMINO-1,2-PROPANEDIOL;Carbamic acid, (2,3-dihydroxypropyl)-, 1,1-dimethylethyl ester (9CI);tert-Butyl (2,3-dihydroxypropyl)carbaMate;tert-Butyl N-(2,3-dihydroxypropyl)carbamate 97%
• IUPAC Name: tert-butylN-(2,3-dihydroxypropyl)carbamate
• Canonical SMILES: CC(C)(C)OC(=O)NCC(CO)O
• InChI Key: OWAMQHJPVUGZSB-UHFFFAOYSA-N
• Boiling Point: 361.6ºC at 760 mmHg
• Melting Point: 60-63°C(lit.)
• Flash Point: 172.5ºC
• Density: 1.136g/cm³
• Exact Mass: 191.11600
• WGK Germany: 3

Case Study

Tert-Butyl N(2,3-Dihydroxypropyl)Carbamate Used in the Synthesis of Diazirinyl Organo-Platinum Complex

Hashimoto M, et al. Chemical and Pharmaceutical Bulletin, 2010, 58(3), 405-407.

The tert-butyl 2,3-diaminopropylcarbamate mother skeleton was synthesized using tert-butyl N(2,3-dihydroxypropyl)carbamate as a raw material, which can be further used in the synthesis of diazirinyl organo-platinum complex. The obtained diazirinyl organo-platinum complex can be used for the manipulations of photoaffinity labeled components.
After deprotection of tert-butoxycarbonyl (Boc) group with an acidic conditions, the amine derivative 3 was reacted with benzoic acid N-succinimidyl ester (4) and diazirinylbenzoic acid N-succinimidyl esters (5, 6) to afford desired products (7-9) in moderate yields.
Taking the synthesis of compound 7 as an example, dichloro[(2,3-diaminopropyl)ammonium] platinum(1) chloride (3) was prepared from tert-butyl 2,3-dihydroxypropylcarbamate 1. N-Succinimidyl bezoate (4) (12.7 mg, 0.058 mmol) was dissolved in DMF (2 ml) and then added to an aqueous solution of compound 3 (13.0 mg, 0.029 mmol), which had been adjusted to a pH of 7 at 0 °C. The resulting reaction mixture was stirred at room temperature for three hours before being concentrated. The remaining residue was then washed sequentially with ethyl acetate and cold water, yielding 7 (11.0 mg, 85%) as a colorless amorphous substance.

Custom Q&A

What is the molecular formula of Boc-(rs)-3-amino-1,2-propanediol?

The molecular formula of Boc-(rs)-3-amino-1,2-propanediol is C8H17NO4.

What is the molecular weight of Boc-(rs)-3-amino-1,2-propanediol?

The molecular weight of Boc-(rs)-3-amino-1,2-propanediol is 191.22 g/mol.

What are the synonyms of Boc-(rs)-3-amino-1,2-propanediol?

The synonyms of Boc-(rs)-3-amino-1,2-propanediol include tert-Butyl (2,3-dihydroxypropyl)carbamate, tert-Butyl N-(2,3-dihydroxypropyl)carbamate, and N-Boc-3-amino-1,2-propanediol.

What is the IUPAC name of Boc-(rs)-3-amino-1,2-propanediol?

The IUPAC name of Boc-(rs)-3-amino-1,2-propanediol is tert-butyl N-(2,3-dihydroxypropyl)carbamate.

What is the InChIKey of Boc-(rs)-3-amino-1,2-propanediol?

The InChIKey of Boc-(rs)-3-amino-1,2-propanediol is OWAMQHJPVUGZSB-UHFFFAOYSA-N.

What is the Canonical SMILES of Boc-(rs)-3-amino-1,2-propanediol?

The Canonical SMILES of Boc-(rs)-3-amino-1,2-propanediol is CC(C)(C)OC(=O)NCC(CO)O.

What is the CAS number of Boc-(rs)-3-amino-1,2-propanediol?

The CAS number of Boc-(rs)-3-amino-1,2-propanediol is 137618-48-5.

What is the XLogP3-AA value of Boc-(rs)-3-amino-1,2-propanediol?

The XLogP3-AA value of Boc-(rs)-3-amino-1,2-propanediol is -0.4.

How many hydrogen bond donor counts does Boc-(rs)-3-amino-1,2-propanediol have?

Boc-(rs)-3-amino-1,2-propanediol has 3 hydrogen bond donor counts.

How many rotatable bond counts does Boc-(rs)-3-amino-1,2-propanediol have?

Boc-(rs)-3-amino-1,2-propanediol has 5 rotatable bond counts.