200065-54-9

Basic information

• Product Name: (S)-3-[4-(Adamantan-2-yloxycarbonyloxy)-phenyl]-2-amino-propionic acid
• Synonyms: (S)-3-[4-(Adamantan-2-yloxycarbonyloxy)-phenyl]-2-amino-propionic acid
• CAS NO: 200065-54-9
• Molecular Weight: 359.422
• Mol File: 200065-54-9.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (S)-3-[4-(Adamantan-2-yloxycarbonyloxy)-phenyl]-2-amino-propionic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-3-[4-(Adamantan-2-yloxycarbonyloxy)-phenyl]-2-amino-propionic acid(200065-54-9)
• EPA Substance Registry System: (S)-3-[4-(Adamantan-2-yloxycarbonyloxy)-phenyl]-2-amino-propionic acid(200065-54-9)

Safety Data

• Hazardous Substances Data: 200065-54-9(Hazardous Substances Data)

Upstream product

• 53120-53-9 2-adamantyl chloroformate 

Downstream Products

• 168764-12-3 Boc-Tyr(2-Adoc)-Asp(O-2-Ada)-Glu(O-cHex)-Gly-OH 
• 200065-56-1 ((S)-6-(Adamantan-2-yloxycarbonylamino)-2-{(S)-3-[4-(adamantan-2-yloxycarbonyloxy)-phenyl]-2-tert-butoxycarbonylamino-propionylamino}-hexanoylamino)-acetic acid benzyl ester 
• 168764-00-9 (S)-3-[4-(Adamantan-2-yloxycarbonyloxy)-phenyl]-2-tert-butoxycarbonylamino-propionic acid 

Relevant articles and documents

Amino acids and peptides. LI. Application of the 2- adamantyloxycarbonyl (2-Adoc) group to the protection of the hydroxyl function of tyrosine in peptide synthesis

A 2-adamantyloxycarbonyl (2-Adoc) group was introduced as a protecting group for the hydroxyl function of tyrosine (Tyr) through the Shotten- Bauman reaction of 2-adamantyloxycarbonyl chloride with the copper complex of Tyr. The 2-Adoc group is stable to trifluoroacetic acid (TFA), 5.0 N HCl/dioxane, hydrogenation over a Pd catalyst and tertiary amine, and is easily removed by treatment with 1M trifluoromethanesulfonic acid (TFMSA)- thioanisole/TFA and HF. Boc-Tyr(2-Adoc)-OH was prepared by the reaction of (Boc)2O and H-Tyr(2-Adoc)-OH in the presence of triethylamine. Boc-Tyr(2- Adoc)-OH was successfully applied to the synthesis of Boc-Ala-Thr-Val- Lys(2-Adoc)-Phe-Lys(2-Adoc)-Tyr(2-Adoc)-Gly-OH, corresponding to the sequence 1-9 of Sulfolobus solfataricus RNase, and Boc-Tyr(2-Adoc)-Asp(O- 2-Ada)-Glu(O-cHex)-Gly-OH, corresponding to the sequence 33-36 of S. solfataricus RNase. Boc-Phe-Lys(2-Adoc)-Tyr(2-Adoc)-Lys(2-Adoc)-Gly-OBzl was treated with anhydrous HF to afford H-Phe-Lys-Tyr-Gly-OH without any side reactions, in a good yield.