Methanesulfonic acid (2S,3R)-3-{4-[(3R,4R,5S)-3,4-bis-benzyloxy-5-(tert-butyl-diphenyl-silanyloxymethyl)-pyrrolidin-(2E)-ylidene]-5-oxo-4,5-dihydro-oxazol-2-yl}-2,3-dihydroxy-2-methyl-propyl ester

Base Information

• Chemical Name: Methanesulfonic acid (2S,3R)-3-{4-[(3R,4R,5S)-3,4-bis-benzyloxy-5-(tert-butyl-diphenyl-silanyloxymethyl)-pyrrolidin-(2E)-ylidene]-5-oxo-4,5-dihydro-oxazol-2-yl}-2,3-dihydroxy-2-methyl-propyl ester
• CAS No.: 205441-89-0
• Molecular Formula: C₄₃H₅₀N₂O₁₀SSi
• Molecular Weight: 815.029

Synonyms:

Chemical Property of Methanesulfonic acid (2S,3R)-3-{4-[(3R,4R,5S)-3,4-bis-benzyloxy-5-(tert-butyl-diphenyl-silanyloxymethyl)-pyrrolidin-(2E)-ylidene]-5-oxo-4,5-dihydro-oxazol-2-yl}-2,3-dihydroxy-2-methyl-propyl ester

Chemical Property:

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Useful:

Technology Process of Methanesulfonic acid (2S,3R)-3-{4-[(3R,4R,5S)-3,4-bis-benzyloxy-5-(tert-butyl-diphenyl-silanyloxymethyl)-pyrrolidin-(2E)-ylidene]-5-oxo-4,5-dihydro-oxazol-2-yl}-2,3-dihydroxy-2-methyl-propyl ester

There total 10 articles about Methanesulfonic acid (2S,3R)-3-{4-[(3R,4R,5S)-3,4-bis-benzyloxy-5-(tert-butyl-diphenyl-silanyloxymethyl)-pyrrolidin-(2E)-ylidene]-5-oxo-4,5-dihydro-oxazol-2-yl}-2,3-dihydroxy-2-methyl-propyl ester 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: 81.0%

methanesulfonyl chloride (124-63-0) + 4-[(3R,4R,5S)-3,4-Bis-benzyloxy-5-(tert-butyl-diphenyl-silanyloxymethyl)-pyrrolidin-(2E)-ylidene]-2-((1R,2S)-1,2,3-trihydroxy-2-methyl-propyl)-4H-oxazol-5-one (205441-88-9) → Methanesulfonic acid (2S,3R)-3-{4-[(3R,4R,5S)-3,4-bis-benzyloxy-5-(tert-butyl-diphenyl-silanyloxymethyl)-pyrrolidin-(2E)-ylidene]-5-oxo-4,5-dihydro-oxazol-2-yl}-2,3-dihydroxy-2-methyl-propyl ester (205441-89-0)

Guidance literature:

With 2,4,6-trimethyl-pyridine;

Reference yield:

(E)-methyl 4-hydroxy-3-methylbut-2-enoate (13866-57-4) → Methanesulfonic acid (2S,3R)-3-{4-[(3R,4R,5S)-3,4-bis-benzyloxy-5-(tert-butyl-diphenyl-silanyloxymethyl)-pyrrolidin-(2E)-ylidene]-5-oxo-4,5-dihydro-oxazol-2-yl}-2,3-dihydroxy-2-methyl-propyl ester (205441-89-0)

Guidance literature:

Multi-step reaction with 10 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

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-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:

(E)-3-(benzyloxymethoxy)methyl-2-butenoic acid (205441-81-2) → Methanesulfonic acid (2S,3R)-3-{4-[(3R,4R,5S)-3,4-bis-benzyloxy-5-(tert-butyl-diphenyl-silanyloxymethyl)-pyrrolidin-(2E)-ylidene]-5-oxo-4,5-dihydro-oxazol-2-yl}-2,3-dihydroxy-2-methyl-propyl ester (205441-89-0)

Guidance literature:

Multi-step reaction with 8 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

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-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; toluene;

upstream raw materials:

methanesulfonyl chloride

4-[(3R,4R,5S)-3,4-Bis-benzyloxy-5-(tert-butyl-diphenyl-silanyloxymethyl)-pyrrolidin-(2E)-ylidene]-2-((1R,2S)-1,2,3-trihydroxy-2-methyl-propyl)-4H-oxazol-5-one

(E)-methyl 4-hydroxy-3-methylbut-2-enoate

(E)-3-(benzyloxymethoxy)methyl-2-butenoic acid

Downstream raw materials:

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

4-[(3R,4R,5S)-3,4-dibenzyloxy-5-(methanesulfonyloxy)methylpyrrolidin-2-ylidene]-2-[(2S)-2,3-epoxy-2-methylpropionyl]-4H-oxazol-5-one

3-Methoxy-5-methyl-naphthalene-1-carboxylic acid (R)-{4-[(3R,4R,5S)-3,4-bis-benzyloxy-5-hydroxymethyl-pyrrolidin-(2E)-ylidene]-5-oxo-4,5-dihydro-oxazol-2-yl}-((S)-2-methyl-oxiranyl)-methyl ester

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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