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Trans-4-fluoro-L-proline
Organic Synthesis Chemistry
- Contents -
¸ñÀû (Object)
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°í¸®ÈÇÕ¹°À» ¸¸µé ¼ö ÀÖ´Â ¹æ¹ý
NÀÌ Æ÷ÇÔµÈ 5°¢Çü °í¸®ÈÇÕ¹°
ÀÌÁß°áÇÕÀ» ¼±ÅÃÀûÀ¸·Î ȯ¿øÇÒ ¼ö ÀÖ´Â ¹æ¹ý
Stereochemistry Á¶Àý ¹æ¹ý
F¸¦ ź¼Ò¿¡ ºÙÀÌ´Â ¹æ¹ý
Leaving group µµÀÔ¹æ¹ý
COOH±âÀÇ µµÀÔ ¹æ¹ý
¾Æ¹Î±â¿¡ ´ëÇÑ protecting group¿¡ °üÇÑ Á¶»ç
ÃÖÁ¾ synthesis scheme
°á·Ð (Conclusion)
Organic Synthesis Chemistry
- Object -
Trans-4-fluoro-L-prolineÀÇ ÇÕ¼º´Ü°è¸¦ Á¶»çÇغ½À¸·Î ¾î¶°ÇÑ À¯±âÈÇÐÀû ¹ÝÀÀÀÌ »ç¿ëµÇ¾ú´ÂÁö ¾Ë¾Æº»´Ù.
¶ÇÇÑ ÀÌ ¹°ÁúÀ» ¸¸µé±â À§ÇØ »ç¿ëµÈ À¯±âÈÇйÝÀÀÀ» ÀÌÇØÇÏ°í ¼³¸íÇÒ ¼ö ÀÖ´Ù.
´Ù¾çÇÑ ÇÕ¼º ¹æ¹ýµé Áß ¹ÝÀÀÀÇ ÇÑ°èÁ¡À» ¾Ë¾Æº¸°í °¡Àå °æÁ¦ÀûÀÌ°í ģȯ°æÀûÀÎ ÇÕ¼º ·çÆ®¸¦ Á¦½ÃÇÒ ¼ö ÀÖ´Ù.
Organic Synthesis Chemistry
°í¸®ÈÇÕ¹°À» ¸¸µé ¼ö ÀÖ´Â ¹æ¹ý
Organic Synthesis Chemistry
NÀÌ Æ÷ÇÔµÈ °í¸®ÈÇÕ¹°À» ¸¸µå´Â¡¦(»ý·«)
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sis Chemistry
Tosylation
À§ÀÇ ±×¸²°ú °°ÀÌ ¾ËÄڿÿ¡ H¸¦ pyridine°ú °°Àº base·Î Àâ¾Æ ¶ì°í
p-toluenesulfonyl chloride¸¦ ÀÌ¿ëÇØ tosyl groupÀ» µµÀÔÇÒ ¼ö ÀÖ´Ù.
COOH±âÀÇ µµÀÔ¹æ¹ý
Organic Synthesis Chemistry
Grignard reagent ÀÌ¿ë
CO2H±âÀÇ µµÀÔÀº À§ÀÇ ±×¸²°ú °°ÀÌ Grignard reagent¸¦ ÀÌ¿ëÇÒ ¼ö ÀÖ´Ù.
COOH±âÀÇ µµÀÔ¹æ¹ý
Organic Synthesis Chemistry
½ÇÁúÀûÀÎ ¿¹
ÀÌÁß°áÇÕÀ» °®´Â ½ÃÀÛ¹°ÁúÀÎ °æ¿ì bromination ½ÃŲ ÈÄ Mg¸¦
ÀÌ¿ëÇØ ¹°ÁúÀÚü¸¦ Grignard reagent·Î ¸¸µç ÈÄ CO2¸¦ ÷°¡½ÃÄÑ
CO2H±â¸¦ µµÀÔÇÑ´Ù.
Protecting group for ?NH2
Organic Synthesis Chemistry
Boc¸¦ ÀÌ¿ëÇÑ protecting
Organic Synthesis Chemistry
Protecting group for ?NH2
Cbz¸¦ ÀÌ¿ëÇÑ protecting
Fmoc¸¦ ÀÌ¿ëÇÑ protecting
carbooxybenzyl
Synthesis Scheme
Organic Synthesis Chemistry
4 stepÀÇ scheme
- Conclusion -
Organic Synthesis Chemistry
À̹ø À¯±âÇÕ¼º ¼³°è ÇÁ·ÎÁ§Æ®¸¦ ÁøÇàÇÏ¸é¼ ¼ö¾÷½Ã°£¿¡ ¹è¿ü´ø À¯±âÇÕ¼º¿¡ ´ëÇÑ ÀÌ·ÐÀ» º¹½ÀÇÏ°í ½ÇÁ¦ ÇÕ¼º¿¡ ÇÊ¿äÇÑ ¿©·¯ Á¶°ÇµéÀ» °±¸ÇØ º¼ ¼ö ÀÖ¾ú´Ù.
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- Organic Chemistry / Oxford University Press, 2001J. Clayden, N. Greeves, S. Warren, P. Wothers - The chemistry of pyrroles / Academic, Jones, R. Alan/Bean, Gerritt P. - Selective fluorination in organic and bioorganic chemistry / American Chemical Society, Welch, John T - À¯±âÇÕ¼º / R. K. Mackie ; D. M. Smith ; R. A. Aitken Àú ; °û¿µ¿ì ¿ª - À¯±âÈÇÐ / Robert Thornton Morrison ; Robert Neilson Boyd°øÀú- Wikipedia , the free encyclopedia - http://www.cem.msu.edu/~reusch/VirtTxtJml/alcohol1.htm
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