4-[(3R,4R,5S)-3,4-Bis-benzyloxy-5-(tert-butyl-diphenyl-silanyloxymethyl)-pyrrolidin-(2E)-ylidene]-2-((S)-2-methyl-oxiranecarbonyl)-4H-oxazol-5-one

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Chemical Name:4-[(3R,4R,5S)-3,4-Bis-benzyloxy-5-(tert-butyl-diphenyl-silanyloxymethyl)-pyrrolidin-(2E)-ylidene]-2-((S)-2-methyl-oxiranecarbonyl)-4H-oxazol-5-one
CAS No.:205441-91-4
Molecular Formula:C₄₂H₄₄N₂O₇Si
Molecular Weight:716.906
Hs Code.:

Synonyms:4-[(3R,4R,5S)-3,4-Bis-benzyloxy-5-(tert-butyl-diphenyl-silanyloxymethyl)-pyrrolidin-(2E)-ylidene]-2-((S)-2-methyl-oxiranecarbonyl)-4H-oxazol-5-one

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Chemical Property of 4-[(3R,4R,5S)-3,4-Bis-benzyloxy-5-(tert-butyl-diphenyl-silanyloxymethyl)-pyrrolidin-(2E)-ylidene]-2-((S)-2-methyl-oxiranecarbonyl)-4H-oxazol-5-one

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Technology Process of 4-[(3R,4R,5S)-3,4-Bis-benzyloxy-5-(tert-butyl-diphenyl-silanyloxymethyl)-pyrrolidin-(2E)-ylidene]-2-((S)-2-methyl-oxiranecarbonyl)-4H-oxazol-5-one

There total 12 articles about 4-[(3R,4R,5S)-3,4-Bis-benzyloxy-5-(tert-butyl-diphenyl-silanyloxymethyl)-pyrrolidin-(2E)-ylidene]-2-((S)-2-methyl-oxiranecarbonyl)-4H-oxazol-5-one which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 92.0%

: 205441-90-3
4-[(3R,4R,5S)-3,4-Bis-benzyloxy-5-(tert-butyl-diphenyl-silanyloxymethyl)-pyrrolidin-(2E)-ylidene]-2-[(R)-hydroxy-((S)-2-methyl-oxiranyl)-methyl]-4H-oxazol-5-one

: 205441-91-4
4-[(3R,4R,5S)-3,4-Bis-benzyloxy-5-(tert-butyl-diphenyl-silanyloxymethyl)-pyrrolidin-(2E)-ylidene]-2-((S)-2-methyl-oxiranecarbonyl)-4H-oxazol-5-one

Guidance literature:: Dess-Martin oxidn.;

Reference yield:

: 13866-57-4
(E)-methyl 4-hydroxy-3-methylbut-2-enoate

: 205441-91-4
4-[(3R,4R,5S)-3,4-Bis-benzyloxy-5-(tert-butyl-diphenyl-silanyloxymethyl)-pyrrolidin-(2E)-ylidene]-2-((S)-2-methyl-oxiranecarbonyl)-4H-oxazol-5-one

Guidance literature:: Multi-step reaction with 12 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.

With 2,4,6-trimethyl-pyridine; sodium hydroxide; sodium tetrahydroborate; osmium(VIII) oxide; Hydroquinone 1,4-phthalazinediyl diether; C₆H₁₁NCNCH₂N(Me)(CH₂CH₂OCH₂CH₂)⁽¹⁺⁾*TsO^(1-); hydrogen sulfide; 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 dichloromethane; toluene;

Reference yield:

: 205441-81-2
(E)-3-(benzyloxymethoxy)methyl-2-butenoic acid

: 205441-91-4
4-[(3R,4R,5S)-3,4-Bis-benzyloxy-5-(tert-butyl-diphenyl-silanyloxymethyl)-pyrrolidin-(2E)-ylidene]-2-((S)-2-methyl-oxiranecarbonyl)-4H-oxazol-5-one

Guidance literature:: Multi-step reaction with 10 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.

With 2,4,6-trimethyl-pyridine; sodium hydroxide; sodium tetrahydroborate; osmium(VIII) oxide; Hydroquinone 1,4-phthalazinediyl diether; C₆H₁₁NCNCH₂N(Me)(CH₂CH₂OCH₂CH₂)⁽¹⁺⁾*TsO^(1-); hydrogen sulfide; 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 dichloromethane; toluene;