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In order to establish whether the overall reaction from enan-tiomer pure N -Boc-phenylalanine leads to any loss of optical purity through partial racemization in presence of base, enantiomeric excess (ee) values of L-Ia and diastereoisomeric excess (de) values based on the stereoconfi guration of amino acid amide part of fi nal product L -IIa obtained from L -N-Boc-phenylalanine were deter-mined. While Boc-deprotected product (free amine) showed an ee of 99.4%, the target compound L-IIa arising through nucleophilic addition of L- Ia on a-phosphateisothiocyanate was obtained in 98.5% de. Thus, as expected, stereochemical configuration at a-carbon atom of the acid was practically unaffected and this synthetic transformation from chiral a-amino acid could be applied to a wide range of compounds without undergoing any signi fi cant loss of optical activity. Since both L- and D -isomers of N -Boc- phenylalanine are easily accessible, it provides a useful route to obtain both the enantiomeric forms of carboxamideIa e c which are useful synthons to a variety of pharmaceuticals. The overall process for novel (L)/(D)- pseudo-peptide thioureasIIae l is convenient, high yielding and atom-economic.

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AnnF: ½ð±Ò+5, ·­ÒëEPI+1, ¡ïÓаïÖú, ÐÁ¿àÁË 2013-01-13 10:44:50
sltmac: ½ð±Ò+10, »¶Ó­³£À´±¾°æ½»Á÷ 2013-02-26 13:23:54
In order to establish whether the overall reaction from enan-tiomer pure N -Boc-phenylalanine leads to any loss of optical purity through partial racemization in presence of base,enantiomeric excess (ee) values of L-Ia and diastereoisomeric excess (de) values based on the stereoconfiguration of amino acid amide part of final product L-IIa obtained from L-N-Boc-phenylalanine were determined.
·­Ò룺ΪÁËÈ·¶¨ ÔÚ¼îµÄ´æÔÚÏ  ´¿µÄµ¥Ò»¶ÔÓ³ÌåN-Êå¶¡ÑõôÊ-±½±û°±Ëá ͨ¹ý²¿·ÖÍâÏûÐý»¯ ¿ªÊ¼µÄÈ«ÃæµÄ·´Ó¦ÊÇ·ñ»áÒý·¢¹âѧ´¿¶ÈµÄËðʧ£¬#

£¨ÎÒÃÇ£©¶Ô L- IA¶ÔÓ³Ìå¹ýÊ£Öµ£¨ee£©µÄ  ºÍ  ´Ó×óÐýµÄN-Êå¶¡ÑõôÊ-±½±û°±ËáÖеĻñµÃµÄ×îÖÕ²úÎïL-IIaµÄ²¿·ÖµÄ°±»ùËáõ£°·µÄÁ¢Ìå¹¹ÐÍ£©µÄ·Ç¶ÔÓ³Ìå¹ýÊ££¨DE£©Öµ½øÐÐÁ˲ⶨ¡£#

While Boc-deprotected product (free amine) showed an ee of 99.4%, the target compound L-IIa arising through nucleophilic addition of L-Ia on a-phosphateisothiocyanate was obtained in 98.5% de.
·­Ò룺µ±N¡ªBoc±£»¤µÄ²úÎÓÎÀë°·£©ÏÔʾµÄ¶ÔÓ³Ìå¹ýÊ£Öµ£¨ee£©ÔÚ99.4%ʱºò£¬Ä¿±ê»¯ºÏÎï L-IIaµÄ·Ç¶ÔÓ³Ìå¹ýÊ£Öµ£¨de£©ÔÚ¾­¹ýL-IaÇ׺˼ӳÉÔÚ ¦Á-Á×ËáÒìÁòÇèËáÑÎÉÏ ¿ÉÒÔÉÏÉýµ½98.5%¡£#

Thus, as expected, stereochemical configuration at a-carbon atom of the acid was practically unaffected and this synthetic transformation from chiral a-amino acid could be applied to a wide range of compounds without undergoing any significant loss of optical activity.
·­Ò룺Òò´Ë£¬ÕýÈçËùÁÏ£¬ËáµÄ¦Á-̼ԭ×ÓµÄÁ¢Ì廯ѧ¹¹ÐÍʵ¼ÊÉϲ»ÊÜÓ°Ï죬²¢ÇÒÕâÖÖ´ÓÊÖÐÔ¦Á-°±»ùËáµÄºÏ³Éת»¯£¨ÖƱ¸»¯ºÏÎ¿ÉÒÔÓ¦Óõ½£¨ÖƱ¸£©¸÷ʽ¸÷ÑùµÄ»¯ºÏÎïÖÐÇÒ²»ÐèÒª¾­¹ý¹âѧ»îÐÔµÄÏÔÖøÉ¥Ê§¡£#

Since both L-and D-isomers of N-Boc-phenylalanine are easily accessible, it provides a useful route to obtain both the enantiomeric forms of carboxamide Ia-c which are useful synthons to a variety of pharmaceuticals.
·­Ò룺ÒòΪL-ÐͺÍD-Ð͵ÄN-Êå¶¡ÑõôÊ-±½±û°±ËáµÄͬ·ÖÒì¹¹ÌåÊÇÈÝÒ׵õ½µÄ£¬ÕâÌṩÁËÒ»ÖÖÓÐÓõÄ;¾¶È¥»ñµÃÁ½¸ö¶ÔÓ³Òì¹¹ÌåÐÎʽµÄ¼×õ£°·Ia -c£¬ÆäÖм×õ£°·Ia -cÊÇ£¨ºÏ³É£©¸÷ÖÖÒ©ÎïµÄÖØÒªµÄ½á¹¹µ¥Ôª¡£#

The overall process for novel  (L)/(D)- pseudo-peptide thioureas IIae-l is convenient, high yielding and atom-economic.
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