(+)-(1S,3S,4R,5R)-(S_S)-N(1R)-N-[1-((tert-butyldimethylsilyl)oxy)methyl-2-methylpropyl]-4-hydroxy-3-phenyl-1-(4-methylphenylsulfonimidoylmethyl)-2-aza-(N-tert-butoxycarbonyl)-bicyclo[3.3.0]octane

Base Information

• Chemical Name: (+)-(1S,3S,4R,5R)-(S_S)-N(1R)-N-[1-((tert-butyldimethylsilyl)oxy)methyl-2-methylpropyl]-4-hydroxy-3-phenyl-1-(4-methylphenylsulfonimidoylmethyl)-2-aza-(N-tert-butoxycarbonyl)-bicyclo[3.3.0]octane
• CAS No.: 886991-13-5
• Molecular Formula: C₃₇H₅₈N₂O₅SSi
• Molecular Weight: 671.029

Synonyms:(+)-(1S,3S,4R,5R)-(S_S)-N(1R)-N-[1-((tert-butyldimethylsilyl)oxy)methyl-2-methylpropyl]-4-hydroxy-3-phenyl-1-(4-methylphenylsulfonimidoylmethyl)-2-aza-(N-tert-butoxycarbonyl)-bicyclo[3.3.0]octane

Chemical Property of (+)-(1S,3S,4R,5R)-(S_S)-N(1R)-N-[1-((tert-butyldimethylsilyl)oxy)methyl-2-methylpropyl]-4-hydroxy-3-phenyl-1-(4-methylphenylsulfonimidoylmethyl)-2-aza-(N-tert-butoxycarbonyl)-bicyclo[3.3.0]octane

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Technology Process of (+)-(1S,3S,4R,5R)-(S_S)-N(1R)-N-[1-((tert-butyldimethylsilyl)oxy)methyl-2-methylpropyl]-4-hydroxy-3-phenyl-1-(4-methylphenylsulfonimidoylmethyl)-2-aza-(N-tert-butoxycarbonyl)-bicyclo[3.3.0]octane

There total 3 articles about (+)-(1S,3S,4R,5R)-(S_S)-N(1R)-N-[1-((tert-butyldimethylsilyl)oxy)methyl-2-methylpropyl]-4-hydroxy-3-phenyl-1-(4-methylphenylsulfonimidoylmethyl)-2-aza-(N-tert-butoxycarbonyl)-bicyclo[3.3.0]octane 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: 44.0%

di-tert-butyl dicarbonate (24424-99-5) + (+)-(SS)-N(1R)-N-[1-((tert-butyldimethylsilyl)oxy)methyl-2-methylpropyl]-S-(cyclopent-1-en-1-ylmethyl)-S-(4-methylphenyl)sulfoximide (177796-05-3) + (+)-(S)-(N-9-fluorenylmethoxycarbonyl)phenylglycinal (250613-50-4) → (+)-(1S,3S,4R,5R)-(SS)-N(1R)-N-[1-((tert-butyldimethylsilyl)oxy)methyl-2-methylpropyl]-4-hydroxy-3-phenyl-1-(4-methylphenylsulfonimidoylmethyl)-2-aza-(N-tert-butoxycarbonyl)-bicyclo[3.3.0]octane (886991-13-5)

Guidance literature:

Multistep reaction;

DOI:10.1021/ja057012a

Reference yield:

(1S,3S,4R,5R)-(SS)-N(1R)-N-[1-((tert-butyldimethylsilyl)oxy)methyl-2-methylpropyl]-4-hydroxy-3-phenyl-1-(4-methylphenylsulfonimidoylmethyl)-2-azabicyclo[3.3.0]octane → (+)-(1S,3S,4R,5R)-(SS)-N(1R)-N-[1-((tert-butyldimethylsilyl)oxy)methyl-2-methylpropyl]-4-hydroxy-3-phenyl-1-(4-methylphenylsulfonimidoylmethyl)-2-aza-(N-tert-butoxycarbonyl)-bicyclo[3.3.0]octane (886991-13-5)

Guidance literature:

With di-tert-butyl dicarbonate; sodium hydrogencarbonate; In 1,4-dioxane; water; for 12h;

Reference yield:

(2-hydroxy-1-phenylethyl)carbamic acid 9H-fluoren-9-ylmethyl ester (215178-44-2) → (+)-(1S,3S,4R,5R)-(SS)-N(1R)-N-[1-((tert-butyldimethylsilyl)oxy)methyl-2-methylpropyl]-4-hydroxy-3-phenyl-1-(4-methylphenylsulfonimidoylmethyl)-2-aza-(N-tert-butoxycarbonyl)-bicyclo[3.3.0]octane (886991-13-5)

Guidance literature:

Multi-step reaction with 2 steps

1: Dess-Martin periodinane / CH₂Cl₂ / 0 - 20 °C

With Dess-Martin periodane; In dichloromethane;

DOI:10.1021/ja057012a

upstream raw materials:

di-tert-butyl dicarbonate

(+)-(S_S)-N(1R)-N-[1-((tert-butyldimethylsilyl)oxy)methyl-2-methylpropyl]-S-(cyclopent-1-en-1-ylmethyl)-S-(4-methylphenyl)sulfoximide

(+)-(S)-(N-9-fluorenylmethoxycarbonyl)phenylglycinal

(2-hydroxy-1-phenylethyl)carbamic acid 9H-fluoren-9-ylmethyl ester

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