Boc-D-Serine Chemical Properties

Melting point:

91-95 °C(lit.)

alpha 

8.5 º (c=1 H2O)

Boiling point:

343.88°C (rough estimate)

Density 

1.2977 (rough estimate)

refractive index 

1.4540 (estimate)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

DMSO (Slightly), Methanol (Slightly)

form 

Solid

pka

3.62±0.10(Predicted)

color 

White

optical activity

13.09°(C=0.4243g/100mI, DMF, 20°C, 589nm)

Water Solubility 

almost transparency

BRN 

1874714

InChI

InChI=1S/C8H15NO5/c1-8(2,3)14-7(13)9-5(4-10)6(11)12/h5,10H,4H2,1-3H3,(H,9,13)(H,11,12)/t5-/m1/s1

InChIKey

FHOAKXBXYSJBGX-RXMQYKEDSA-N

SMILES

C(O)(=O)[C@@H](CO)NC(OC(C)(C)C)=O

CAS DataBase Reference

6368-20-3(CAS DataBase Reference)

Safety Information

Safety Statements 

24/25

WGK Germany 

3

HS Code 

29241990

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

Boc-D-Serine Usage And Synthesis

Chemical Properties

White powder

Uses

Boc-D-serine is D-serine (S270975) with amine protected from eletrophiles by tert-butyloxycarbonyl group in organic synthesis. Boc-D-serine can be used to synthesize acetamido-methoxypropionamides such as Desacetyl Desmethyl Lacosamide (D288325) which is a potent anticonvulsant.

reaction suitability

reaction type: Boc solid-phase peptide synthesis

Synthesis

1. An aqueous solution of sodium hydroxide (8.4 g, 0.110 mol) was prepared by dissolving sodium hydroxide (8.4 g, 0.110 mol) in water (53 mL) at room temperature. 2. The above solution was cooled down to 5-10 °C. 3. To the cooled aqueous solution of sodium hydroxide was added sequentially D-serine (10.5 g, 0.100 mol) and di-tert-butyl dicarbonate (26.2 g, 0.120 mol), while the temperature was maintained at ≤ 10 °C. 4. 26.2 g, 0.120 mol). 4. The reaction mixture was heated to 30-35 °C and stirred at this temperature for 20 h. 5. Upon completion of the reaction, an aqueous solution of compound I (BOC-L-serine) was obtained in 100% yield, with 99.1% HPLC purity and 99.4% chiral purity. 6. The aqueous solution of compound I did not need to be further purified and could be used directly in the subsequent synthetic step. 7. The aqueous solution of compound I can be used directly in the subsequent synthesis steps.

References

[1] Journal of the American Chemical Society, 1994, vol. 116, # 18, p. 8402 - 8403
[2] Journal of the American Chemical Society, 2008, vol. 130, # 7, p. 2351 - 2364
[3] Advanced Synthesis and Catalysis, 2016, vol. 358, # 1, p. 34 - 40
[4] Patent: CN104030943, 2016, B. Location in patent: Paragraph 0095; 0096
[5] Beilstein Journal of Organic Chemistry, 2014, vol. 10, p. 1114 - 1120

Boc-D-Serine(6368-20-3)Related Product Information

• D-Cycloserine
• N-Carbobenzyloxyglycine
• L-CYCLOSERINE
• tert-Butanol
• L-Homoserine
• L-Serine
• L-ALPHA-PHOSPHATIDYLSERINES, BRAIN, BOVINE
• D-Serine
• DL-Serine
• L-Valine methyl ester hydrochloride
• D-Valine
• N-BOC-O-Benzyl-L-serine
• DIETHYL (BOC-AMINO)MALONATE
• DIMETHYL (BOC-AMINO)MALONATE
• N-(tert-Butoxycarbonyl)-O-benzyl-D-threonine
• BOC-D-THR-OH
• BOC-D-SERINE METHYL ESTER,BOC-D-SERINE METHYLESTER OIL,N-BOC-D-serine methylester
• Boc-Ser(tBu)-OH