Technology Process of 3-Methoxy-5-methyl-naphthalene-1-carboxylic acid (S)-{4-[(3R,4R,5S)-3,4-bis-benzyloxy-5-methanesulfonyloxymethyl-pyrrolidin-(2E)-ylidene]-5-oxo-4,5-dihydro-oxazol-2-yl}-((S)-2-methyl-oxiranyl)-methyl ester
There total 16 articles about 3-Methoxy-5-methyl-naphthalene-1-carboxylic acid (S)-{4-[(3R,4R,5S)-3,4-bis-benzyloxy-5-methanesulfonyloxymethyl-pyrrolidin-(2E)-ylidene]-5-oxo-4,5-dihydro-oxazol-2-yl}-((S)-2-methyl-oxiranyl)-methyl ester which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
With
dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride;
- Guidance literature:
-
Multi-step reaction with 16 steps
1: i-Pr2NEt
2: aq. NaOH
3: 1-ethyl 3-(dimethylaminopropyl)carbodiimide hydrochloride, Et3N
4: 92 percent / aq. NaOH
5: 100 percent / C6H11NCNCH2N(Me)(CH2CH2OCH2CH2)(1+)*TsO(1-)
6: 58 percent / toluene / 60 °C
7: DDQ
8: NaBH4
9: 59 percent / 1.) (DHQ)2PHAL, OsO4; 2.) H2S / CH2Cl2 / -15 °C
10: 81 percent / γ-collidine
11: 84 percent / DBU
12: 92 percent / Dess-Martin oxidn.
13: TBAF
14: γ-collidine
15: NaBH4, CeCl3*7H2O / methanol / 0 °C
16: 91 percent / 1-ethyl 3-(dimethylaminopropyl)carbodiimide hydrochloride, DMAP
With
2,4,6-trimethyl-pyridine; dmap; sodium hydroxide; sodium tetrahydroborate; osmium(VIII) oxide; cerium(III) chloride; Hydroquinone 1,4-phthalazinediyl diether; C6H11NCNCH2N(Me)(CH2CH2OCH2CH2)(1+)*TsO(1-); hydrogen sulfide; tetrabutyl ammonium fluoride; 1,8-diazabicyclo[5.4.0]undec-7-ene; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone;
In
methanol; dichloromethane; toluene;
- Guidance literature:
-
Multi-step reaction with 14 steps
1: 1-ethyl 3-(dimethylaminopropyl)carbodiimide hydrochloride, Et3N
2: 92 percent / aq. NaOH
3: 100 percent / C6H11NCNCH2N(Me)(CH2CH2OCH2CH2)(1+)*TsO(1-)
4: 58 percent / toluene / 60 °C
5: DDQ
6: NaBH4
7: 59 percent / 1.) (DHQ)2PHAL, OsO4; 2.) H2S / CH2Cl2 / -15 °C
8: 81 percent / γ-collidine
9: 84 percent / DBU
10: 92 percent / Dess-Martin oxidn.
11: TBAF
12: γ-collidine
13: NaBH4, CeCl3*7H2O / methanol / 0 °C
14: 91 percent / 1-ethyl 3-(dimethylaminopropyl)carbodiimide hydrochloride, DMAP
With
2,4,6-trimethyl-pyridine; dmap; sodium hydroxide; sodium tetrahydroborate; osmium(VIII) oxide; cerium(III) chloride; Hydroquinone 1,4-phthalazinediyl diether; C6H11NCNCH2N(Me)(CH2CH2OCH2CH2)(1+)*TsO(1-); hydrogen sulfide; tetrabutyl ammonium fluoride; 1,8-diazabicyclo[5.4.0]undec-7-ene; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone;
In
methanol; dichloromethane; toluene;