(+/-)-BOC-ALPHA-PHOSPHONOGLYCINE TRIMETHYL ESTER Chemical Properties

Melting point:

67-71°C

Boiling point:

398.6±37.0 °C(Predicted)

Density 

1.204±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

Chloroform (Slightly), Methanol (Slightly)

pka

9.63±0.46(Predicted)

form 

Powder or Crystalline Powder

color 

White to off-white

Water Solubility 

Insoluble in water.

BRN 

4296364

Major Application

peptide synthesis

InChI

InChI=1S/C10H20NO7P/c1-10(2,3)18-9(13)11-7(8(12)15-4)19(14,16-5)17-6/h7H,1-6H3,(H,11,13)

InChIKey

LJHAPRKTPAREGO-UHFFFAOYSA-N

SMILES

C(OC)(=O)C(P(OC)(OC)=O)NC(OC(C)(C)C)=O

Safety Information

Hazard Codes 

T

Risk Statements 

25

Safety Statements 

45

RIDADR 

UN 2811 6.1/PG 3

WGK Germany 

3

F 

10

HazardClass 

6.1

PackingGroup 

Ⅲ

HS Code 

29319090

Storage Class

6.1C - Combustible acute toxic Cat.3
toxic compounds or compounds which causing chronic effects

Hazard Classifications

Acute Tox. 3 Oral

MSDS

• Language:English Provider:SigmaAldrich

(+/-)-BOC-ALPHA-PHOSPHONOGLYCINE TRIMETHYL ESTER Usage And Synthesis

Chemical Properties

White solid

Uses

It is used as Wittig-Horner reagent for preparing (Z)-Boc-protected dehydroamino acid derivatives and saturated, unnatural amino acids by subsequent asymmetric hydrogenation.

Uses

(+/-)-Boc-a-phosphonoglycine trimethyl ester is used as a Wittig-Horner reagent for preparing (Z)-Boc-protected dehydroamino acid derivatives.

reaction suitability

reaction type: Boc solid-phase peptide synthesis

Synthesis

Step 1: In a round-bottomed flask equipped with a reflux condenser, a suspension of Cbz methoxyglycine methyl ester 35 (5.98 g, 23.6 mmol) in toluene (25 mL) was heated to 70??C under nitrogen with stirring to dissolve the solids. Phosphorus trichloride (freshly distilled) was added (1.96) mL, 23.6 mmol) and the reaction was stirred at 70??C for 24 hours. Add trimethyl phosphite (2.08 ) mL, 23.6 mmol) and the reaction was stirred at 70??C for 3 hours. The solvent was evaporated and the residue was dissolved in EtOAc (50 mL). The residue was diluted with ice-cold saturated NaHCO3 (3 x 10) mL), water (10 mL), and brine (25 mL) to wash the organic solution and then dried with anhydrous MgSO4. The solvent was removed and the residue was recrystallized from EtOAc/hexane to give 7.03 g (90%) white powder (??)-BOC-A-phosphorylglycine trimethyl ester. mp 78 degrees Celsius.

Step 2: Phosphoglycerol ester 36 (2.00 g, 6.04 mmol) and di-tert-butyl dicarbonate were dissolved in methanol (15 mL) in a Parr shaker hydrogenation flask and degassed with N2 for 15 min. Carbon-loaded palladium (10%, 100 ) was added. mg) and the solution was shaken for 3 h at room temperature under 40 psi H2. The solvent was concentrated and the residue dissolved in EtOAc (30 mL). The solution was diluted with saturated NaCO3 (3 x 10 ) mL), water (10 mL) and brine (20 mL) to wash the organic solution and then dried over MgSO4. The solvent was concentrated and the product precipitated by the addition of hexane to give 1.55 g (86%) white solid (??)-BOC-A-phosphorylglycine trimethyl ester.

Purification Methods

(+/-)-Boc-a-phosphonoglycine trimethyl ester is purified by recrystallization from diethyl ether/pentane (1:1) at 0 °C.

Precautions

(+/-)-Boc-a-phosphonoglycine trimethyl ester is a reagent should be used in a fume hood.

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