Methanesulfonic acid (2S,3R,4R)-3,4-bis-benzyloxy-5-[2-[(S)-hydroxy-((S)-2-methyl-oxiranyl)-methyl]-5-oxo-oxazol-(4E)-ylidene]-pyrrolidin-2-ylmethyl ester

Base Information

Chemical Name:Methanesulfonic acid (2S,3R,4R)-3,4-bis-benzyloxy-5-[2-[(S)-hydroxy-((S)-2-methyl-oxiranyl)-methyl]-5-oxo-oxazol-(4E)-ylidene]-pyrrolidin-2-ylmethyl ester
CAS No.:205441-76-5
Molecular Formula:C₂₇H₃₀N₂O₉S
Molecular Weight:558.609
Hs Code.:

Methanesulfonic acid (2S,3R,4R)-3,4-bis-benzyloxy-5-[2-[(S)-hydroxy-((S)-2-methyl-oxiranyl)-methyl]-5-oxo-oxazol-(4E)-ylidene]-pyrrolidin-2-ylmethyl ester

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Chemical Property of Methanesulfonic acid (2S,3R,4R)-3,4-bis-benzyloxy-5-[2-[(S)-hydroxy-((S)-2-methyl-oxiranyl)-methyl]-5-oxo-oxazol-(4E)-ylidene]-pyrrolidin-2-ylmethyl ester

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Technology Process of Methanesulfonic acid (2S,3R,4R)-3,4-bis-benzyloxy-5-[2-[(S)-hydroxy-((S)-2-methyl-oxiranyl)-methyl]-5-oxo-oxazol-(4E)-ylidene]-pyrrolidin-2-ylmethyl ester

There total 15 articles about Methanesulfonic acid (2S,3R,4R)-3,4-bis-benzyloxy-5-[2-[(S)-hydroxy-((S)-2-methyl-oxiranyl)-methyl]-5-oxo-oxazol-(4E)-ylidene]-pyrrolidin-2-ylmethyl 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:

: 205441-92-5
4-[(3R,4R,5S)-3,4-dibenzyloxy-5-(methanesulfonyloxy)methylpyrrolidin-2-ylidene]-2-[(2S)-2,3-epoxy-2-methylpropionyl]-4H-oxazol-5-one

: 205441-76-5
Methanesulfonic acid (2S,3R,4R)-3,4-bis-benzyloxy-5-[2-[(S)-hydroxy-((S)-2-methyl-oxiranyl)-methyl]-5-oxo-oxazol-(4E)-ylidene]-pyrrolidin-2-ylmethyl ester

: Methanesulfonic acid (2S,3R,4R)-3,4-bis-benzyloxy-5-[2-[(R)-hydroxy-((S)-2-methyl-oxiranyl)-methyl]-5-oxo-oxazol-(4E)-ylidene]-pyrrolidin-2-ylmethyl ester

Guidance literature:: With sodium tetrahydroborate; cerium(III) chloride; In methanol; at 0 ℃; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

Reference yield:

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

: 205441-76-5
Methanesulfonic acid (2S,3R,4R)-3,4-bis-benzyloxy-5-[2-[(S)-hydroxy-((S)-2-methyl-oxiranyl)-methyl]-5-oxo-oxazol-(4E)-ylidene]-pyrrolidin-2-ylmethyl ester

Guidance literature:: Multi-step reaction with 15 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

With 2,4,6-trimethyl-pyridine; 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;

Reference yield:

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

: 205441-76-5
Methanesulfonic acid (2S,3R,4R)-3,4-bis-benzyloxy-5-[2-[(S)-hydroxy-((S)-2-methyl-oxiranyl)-methyl]-5-oxo-oxazol-(4E)-ylidene]-pyrrolidin-2-ylmethyl ester

Guidance literature:: Multi-step reaction with 13 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

With 2,4,6-trimethyl-pyridine; 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;