(4R,5R)-diphenyl-3-((2'R)-hydroxy-(3'R)-4'-isopropylidendioxy-(1'S)-methyl-(S_S)-sulfinyl)butylisoxazoline

Base Information

• Chemical Name: (4R,5R)-diphenyl-3-((2'R)-hydroxy-(3'R)-4'-isopropylidendioxy-(1'S)-methyl-(S_S)-sulfinyl)butylisoxazoline
• CAS No.: 335066-58-5
• Molecular Formula: C₂₃H₂₇NO₅S
• Molecular Weight: 429.537

Synonyms:(4R,5R)-diphenyl-3-((2'R)-hydroxy-(3'R)-4'-isopropylidendioxy-(1'S)-methyl-(S_S)-sulfinyl)butylisoxazoline

Chemical Property of (4R,5R)-diphenyl-3-((2'R)-hydroxy-(3'R)-4'-isopropylidendioxy-(1'S)-methyl-(S_S)-sulfinyl)butylisoxazoline

Chemical Property:

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Technology Process of (4R,5R)-diphenyl-3-((2'R)-hydroxy-(3'R)-4'-isopropylidendioxy-(1'S)-methyl-(S_S)-sulfinyl)butylisoxazoline

There total 2 articles about (4R,5R)-diphenyl-3-((2'R)-hydroxy-(3'R)-4'-isopropylidendioxy-(1'S)-methyl-(S_S)-sulfinyl)butylisoxazoline 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: 20.0%

2,3-isopropylidene-glyceraldehyde (15186-48-8) + (Ss,4R,5R)-4,5-diphenyl-3-(methylsulfinyl)methylisoxazoline (335066-49-4) → (4R,5R)-diphenyl-3-(2'-hydroxy-(3'R)-4'-isopropylidendioxy-1'-(SS)-methylsulfinyl)butylisoxazoline + (4R,5R)-diphenyl-3-((2'R)-hydroxy-(3'R)-4'-isopropylidendioxy-(1'S)-methyl-(SS)-sulfinyl)butylisoxazoline (335066-58-5)

Guidance literature:

(Ss,4R,5R)-4,5-diphenyl-3-(methylsulfinyl)methylisoxazoline; With lithium diisopropyl amide; In tetrahydrofuran; at -90 ℃; for 2h;

2,3-isopropylidene-glyceraldehyde; In tetrahydrofuran; at -90 ℃; for 1h;

DOI:10.1016/S0957-4166(00)00453-5

Reference yield:

trans-4,5-diphenyl-3-methylisoxazoline (21453-81-6,42948-77-6) → (4R,5R)-diphenyl-3-((2'R)-hydroxy-(3'R)-4'-isopropylidendioxy-(1'S)-methyl-(SS)-sulfinyl)butylisoxazoline (335066-58-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: LDA / tetrahydrofuran / 4 h / -80 °C

1.2: tetrahydrofuran / 0.5 h / -80 °C

2.1: LDA / tetrahydrofuran / 2 h / -90 °C

2.2: 48 percent / tetrahydrofuran / 1 h / -90 °C

With lithium diisopropyl amide; In tetrahydrofuran; 1.2: Andersen reaction / 2.2: Andersen reaction;

DOI:10.1016/S0957-4166(00)00453-5

Reference yield:

(4R,5R)-diphenyl-3-((2'R)-hydroxy-(3'R)-4'-isopropylidendioxy-(1'S)-methyl-(SS)-sulfinyl)butylisoxazoline (335066-58-5) → (1R,2S,5S,6R)-1,2-diphenyl-1,5-dihydroxy-6,7-isopropylidenedioxy-3-heptanone

Guidance literature:

With hydrogen; boric acid; W-2 Raney nickel; In methanol; water; at 0 ℃; for 1h;

DOI:10.1016/S0957-4166(02)00030-7

upstream raw materials:

2,3-isopropylidene-glyceraldehyde

(Ss,4R,5R)-4,5-diphenyl-3-(methylsulfinyl)methylisoxazoline

trans-4,5-diphenyl-3-methylisoxazoline

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