Huagongshe화공사 화학 정보 인쇄 보고서 · 연구 참고용
Ether, bis(1-chloroethyl) → N-benzoyl-O-(1-ethoxyethyl)-3-phenyl-isoserine
참여 물질
| 역할 | 이름 | HCID | 투입량 |
|---|---|---|---|
| 반응물 | Ether, bis(1-chloroethyl) | HCID 23419 | — |
| 반응물 | 3-Benzoylamino-2-hydroxy-3-phenyl-propionic acid | HCID 3315046 | — |
| 용매 | Dichloromethane | HCID 6344 | — |
| 생성물 | N-benzoyl-O-(1-ethoxyethyl)-3-phenyl-isoserine | HCID 67714526 | — |
반응 단계
The epoxide of the cis-cinnamate is then regioselectively opened to produce 3-phenyl isoserinamide. This 3-phenyl isoserinamide is hydrolyzed to produce 3-phenyl-isoserine, which in turn is reacted with benzoyl chloride to form N-benzoyl-3-phenyl-isoserine. Next, the N-benzoyl-3-phenyl-isoserine is reacted with 1-chloroethyl ether and a tertiary amine in methylene chloride to form N-benzoyl-O-(1-ethoxyethyl)-3-phenyl-isoserine. Then, N-benzoyl-O-(1-ethoxyethyl)-3-phenyl-isoserine is reacted with the alcohol shown below: ##STR8## This resulting intermediate is converted to taxol by hydrolytically removing the 1-ethoxyethyl and triethylsilyl protecting groups.
출처 및 근거
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 특허 번호 | US05663393 |
| 출처 데이터셋 | uspto-grants-1997_09 |
| ORD ID | ord-9b71bf70ef614f7191b2f7e2a5cc8913 |
| 출처 메모 | uspto-grants-1997_09 |