(2S,3S,4S)-4-Benzyloxy-2-[(R)-((2R,3S,4R,5R)-3,4-bis-benzyloxy-5-phenylsulfanyl-tetrahydro-furan-2-ylmethoxy)-(4-methoxy-phenyl)-methyl]-3-hydroxy-pyrrolidine-1-carboxylic acid benzyl ester

Base Information

Chemical Name:(2S,3S,4S)-4-Benzyloxy-2-[(R)-((2R,3S,4R,5R)-3,4-bis-benzyloxy-5-phenylsulfanyl-tetrahydro-furan-2-ylmethoxy)-(4-methoxy-phenyl)-methyl]-3-hydroxy-pyrrolidine-1-carboxylic acid benzyl ester
CAS No.:160140-46-5
Molecular Formula:C₅₂H₅₃NO₉S
Molecular Weight:868.06
Hs Code.:

(2S,3S,4S)-4-Benzyloxy-2-[(R)-((2R,3S,4R,5R)-3,4-bis-benzyloxy-5-phenylsulfanyl-tetrahydro-furan-2-ylmethoxy)-(4-methoxy-phenyl)-methyl]-3-hydroxy-pyrrolidine-1-carboxylic acid benzyl ester

Synonyms:(2S,3S,4S)-4-Benzyloxy-2-[(R)-((2R,3S,4R,5R)-3,4-bis-benzyloxy-5-phenylsulfanyl-tetrahydro-furan-2-ylmethoxy)-(4-methoxy-phenyl)-methyl]-3-hydroxy-pyrrolidine-1-carboxylic acid benzyl ester

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Chemical Property of (2S,3S,4S)-4-Benzyloxy-2-[(R)-((2R,3S,4R,5R)-3,4-bis-benzyloxy-5-phenylsulfanyl-tetrahydro-furan-2-ylmethoxy)-(4-methoxy-phenyl)-methyl]-3-hydroxy-pyrrolidine-1-carboxylic acid benzyl ester

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Technology Process of (2S,3S,4S)-4-Benzyloxy-2-[(R)-((2R,3S,4R,5R)-3,4-bis-benzyloxy-5-phenylsulfanyl-tetrahydro-furan-2-ylmethoxy)-(4-methoxy-phenyl)-methyl]-3-hydroxy-pyrrolidine-1-carboxylic acid benzyl ester

There total 34 articles about (2S,3S,4S)-4-Benzyloxy-2-[(R)-((2R,3S,4R,5R)-3,4-bis-benzyloxy-5-phenylsulfanyl-tetrahydro-furan-2-ylmethoxy)-(4-methoxy-phenyl)-methyl]-3-hydroxy-pyrrolidine-1-carboxylic acid benzyl 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: 90.0%

: 160140-45-4
(2R,3S,4S)-4-Benzyloxy-2-[(R)-((2R,3S,4R,5R)-3,4-bis-benzyloxy-5-phenylsulfanyl-tetrahydro-furan-2-ylmethoxy)-(4-methoxy-phenyl)-methyl]-3-(tetrahydro-pyran-2-yloxy)-pyrrolidine-1-carboxylic acid benzyl ester

: 160140-46-5
(2S,3S,4S)-4-Benzyloxy-2-[(R)-((2R,3S,4R,5R)-3,4-bis-benzyloxy-5-phenylsulfanyl-tetrahydro-furan-2-ylmethoxy)-(4-methoxy-phenyl)-methyl]-3-hydroxy-pyrrolidine-1-carboxylic acid benzyl ester

Guidance literature:: With camphor-10-sulfonic acid; In 1,4-dioxane; methanol; for 2h; Ambient temperature;
DOI:10.1016/S0040-4039(00)76839-0

Reference yield:

: 501-53-1,94274-21-2
benzyl chloroformate

: 160140-46-5
(2S,3S,4S)-4-Benzyloxy-2-[(R)-((2R,3S,4R,5R)-3,4-bis-benzyloxy-5-phenylsulfanyl-tetrahydro-furan-2-ylmethoxy)-(4-methoxy-phenyl)-methyl]-3-hydroxy-pyrrolidine-1-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: K₂CO₃ / tetrahydrofuran; H₂O / 0.5 h / 25 °C

2: dl-10-camphorosulfonic acid / CH₂Cl₂ / 0.5 h / 25 °C

3: 91 percent / DIBAL / toluene / 0.5 h / -78 °C

4: 1.) n-BuLi, MS 4A / 1.) DMF, hexane, 0 deg C, 5 min, 2.) DMF, 25 deg C, 0.5 h

5: 90 percent / dl-10-camphorosulfonic acid / methanol; dioxane / 2 h / 25 °C

With n-butyllithium; DL-10-camphorsulfonic acid; diisobutylaluminium hydride; potassium carbonate; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; toluene;
DOI:10.1246/bcsj.67.3057

Reference yield:

: (3R,4R,5R)-4-Benzyloxy-5-hydroxymethyl-2-phenylsulfanyl-tetrahydro-furan-3-ol

: 160140-46-5
(2S,3S,4S)-4-Benzyloxy-2-[(R)-((2R,3S,4R,5R)-3,4-bis-benzyloxy-5-phenylsulfanyl-tetrahydro-furan-2-ylmethoxy)-(4-methoxy-phenyl)-methyl]-3-hydroxy-pyrrolidine-1-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: imidazole / dimethylformamide / 0.5 h / 25 °C

2: tetrabutylammonium iodide, NaH / tetrahydrofuran / 2 h / 25 °C

3: (n-Bu₄)NF / tetrahydrofuran / 0.5 h / 25 °C

4: triethylamine / CH₂Cl₂ / 0.08 h / -78 °C

5: 1.) n-BuLi, MS 4A / 1.) DMF, hexane, 0 deg C, 5 min, 2.) DMF, 25 deg C, 0.5 h

6: 90 percent / dl-10-camphorosulfonic acid / methanol; dioxane / 2 h / 25 °C

With 1H-imidazole; n-butyllithium; DL-10-camphorsulfonic acid; tetrabutyl ammonium fluoride; tetra-(n-butyl)ammonium iodide; sodium hydride; triethylamine; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1246/bcsj.67.3057