(+)-(3R,4R,R_S)-5-benzyloxy-1-(tert-butylsulfinyl)-4-hydroxy-3-methylpentan-2-one

Base Information

• Chemical Name: (+)-(3R,4R,R_S)-5-benzyloxy-1-(tert-butylsulfinyl)-4-hydroxy-3-methylpentan-2-one
• CAS No.: 887915-38-0
• Molecular Formula: C₁₇H₂₆O₄S
• Molecular Weight: 326.457

Synonyms:(+)-(3R,4R,R_S)-5-benzyloxy-1-(tert-butylsulfinyl)-4-hydroxy-3-methylpentan-2-one

Chemical Property of (+)-(3R,4R,R_S)-5-benzyloxy-1-(tert-butylsulfinyl)-4-hydroxy-3-methylpentan-2-one

Chemical Property:

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Technology Process of (+)-(3R,4R,R_S)-5-benzyloxy-1-(tert-butylsulfinyl)-4-hydroxy-3-methylpentan-2-one

There total 2 articles about (+)-(3R,4R,R_S)-5-benzyloxy-1-(tert-butylsulfinyl)-4-hydroxy-3-methylpentan-2-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:

benzyloxyacetoaldehyde (60656-87-3) + (RS)-3-bromo-1-(tert-butylsulfinyl)butan-2-one (503830-54-4) → (+)-(3R,4R,RS)-5-benzyloxy-1-(tert-butylsulfinyl)-4-hydroxy-3-methylpentan-2-one (887915-38-0) + (3S,4S)-5-Benzyloxy-4-hydroxy-3-methyl-1-((R)-2-methyl-propane-2-sulfinyl)-pentan-2-one

Guidance literature:

With samarium diiodide; In tetrahydrofuran; at -78 ℃; for 4h;

DOI:10.1002/ejoc.200500782

Reference yield:

(R)-tert-butyl methyl sulfoxide (20580-80-7) → (+)-(3R,4R,RS)-5-benzyloxy-1-(tert-butylsulfinyl)-4-hydroxy-3-methylpentan-2-one (887915-38-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 95 percent / lithium diisopropylamide / tetrahydrofuran / -78 °C

2: samarium diiodide / tetrahydrofuran / 4 h / -78 °C

With samarium diiodide; lithium diisopropyl amide; In tetrahydrofuran;

DOI:10.1002/ejoc.200500782

Reference yield: 96.0%

(+)-(3R,4R,RS)-5-benzyloxy-1-(tert-butylsulfinyl)-4-hydroxy-3-methylpentan-2-one (887915-38-0) → (+)-(3R,4R)-5-benzyloxy-4-hydroxy-3-methylpentan-2-one (177581-71-4)

Guidance literature:

With aluminium amalgam; In tetrahydrofuran; water; at 15 - 20 ℃; for 1h;

DOI:10.1002/ejoc.200500782

upstream raw materials:

benzyloxyacetoaldehyde

(R_S)-3-bromo-1-(tert-butylsulfinyl)butan-2-one

(R)-tert-butyl methyl sulfoxide

Downstream raw materials:

(+)-(3R,4R)-5-benzyloxy-4-hydroxy-3-methylpentan-2-one

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