(2R,3R)-5-iodo-2,3-(O-isopropylidenedioxy)-4-[2-(tert-butyldiphenylsilyloxy)ethyl]-4-cyclopent-4(exo)en-1-one

Base Information

• Chemical Name: (2R,3R)-5-iodo-2,3-(O-isopropylidenedioxy)-4-[2-(tert-butyldiphenylsilyloxy)ethyl]-4-cyclopent-4(exo)en-1-one
• CAS No.: 1373313-82-6
• Molecular Formula: C₂₆H₃₁IO₄Si
• Molecular Weight: 562.52

Synonyms:(2R,3R)-5-iodo-2,3-(O-isopropylidenedioxy)-4-[2-(tert-butyldiphenylsilyloxy)ethyl]-4-cyclopent-4(exo)en-1-one

Chemical Property of (2R,3R)-5-iodo-2,3-(O-isopropylidenedioxy)-4-[2-(tert-butyldiphenylsilyloxy)ethyl]-4-cyclopent-4(exo)en-1-one

Chemical Property:

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Technology Process of (2R,3R)-5-iodo-2,3-(O-isopropylidenedioxy)-4-[2-(tert-butyldiphenylsilyloxy)ethyl]-4-cyclopent-4(exo)en-1-one

There total 11 articles about (2R,3R)-5-iodo-2,3-(O-isopropylidenedioxy)-4-[2-(tert-butyldiphenylsilyloxy)ethyl]-4-cyclopent-4(exo)en-1-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: 16.0%

(2R,3R)-2,3-(O-isopropylidenedioxy)-4-[2-(tert-butyldiphenylsilyloxy)ethyl]-4-cyclopenten-1-one (1373313-80-4) → (2R,3R)-5-iodo-2,3-(O-isopropylidenedioxy)-4-[2-(tert-butyldiphenylsilyloxy)ethyl]-4-cyclopent-4(exo)en-1-one (1373313-82-6) + (2R,3R)-5-iodo-2,3-(O-isopropylidenedioxy)-4-[2-(tert-butyldiphenylsilyloxy)ethyl]-4-cyclopenten-1-one (1373313-81-5)

Guidance literature:

With pyridine; iodine; In dichloromethane; at 0 - 20 ℃; for 8.25h; Inert atmosphere;

DOI:10.1021/ol300667q

Reference yield:

2,3-O-isopropylidene-D-ribofuranose (67814-68-0,70266-87-4,76249-50-8,76249-51-9,93451-15-1,4099-88-1) → (2R,3R)-5-iodo-2,3-(O-isopropylidenedioxy)-4-[2-(tert-butyldiphenylsilyloxy)ethyl]-4-cyclopent-4(exo)en-1-one (1373313-82-6) + (2R,3R)-5-iodo-2,3-(O-isopropylidenedioxy)-4-[2-(tert-butyldiphenylsilyloxy)ethyl]-4-cyclopenten-1-one (1373313-81-5)

Guidance literature:

Multi-step reaction with 10 steps

1.1: tetrahydrofuran / 6 h / -78 - 20 °C

1.2: 0 °C

2.1: sodium periodate / dichloromethane / 1 h / 0 - 20 °C

3.1: n-butyllithium; lithium diisopropyl amide / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere

3.2: 12.5 h / -78 - 20 °C / Inert atmosphere

3.3: Inert atmosphere

4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 0 - 20 °C

5.1: Grubbs catalyst first generation / dichloromethane / 24 h

6.1: tetrahydrofuran / 4 h / 0 - 20 °C / Inert atmosphere

7.1: sodium perborate tetrahydrate / tetrahydrofuran; water / 15 h / 20 °C / Inert atmosphere

8.1: 1H-imidazole / dichloromethane / 0.5 h / -10 - 0 °C

9.1: tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide / dichloromethane / 4 h / 0 - 20 °C / Inert atmosphere; Molecular sieve

10.1: pyridine; iodine / dichloromethane / 8.25 h / 0 - 20 °C / Inert atmosphere

With pyridine; 1H-imidazole; Grubbs catalyst first generation; sodium periodate; n-butyllithium; tetrapropylammonium perruthennate; sodium perborate tetrahydrate; tetrabutyl ammonium fluoride; iodine; 4-methylmorpholine N-oxide; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; water;

DOI:10.1021/ol300667q

Reference yield:

(-)-(1R)-1-[(4R,5S)-5-((1S)-1-hydroxyallyl)-2,2-dimethyl[1,3]dioxolan-4-yl]ethane-1,2-diol (141436-58-0,126113-84-6) → (2R,3R)-5-iodo-2,3-(O-isopropylidenedioxy)-4-[2-(tert-butyldiphenylsilyloxy)ethyl]-4-cyclopent-4(exo)en-1-one (1373313-82-6) + (2R,3R)-5-iodo-2,3-(O-isopropylidenedioxy)-4-[2-(tert-butyldiphenylsilyloxy)ethyl]-4-cyclopenten-1-one (1373313-81-5)

Guidance literature:

Multi-step reaction with 8 steps

1.1: sodium periodate / dichloromethane / 1 h / 0 - 20 °C

2.1: n-butyllithium; lithium diisopropyl amide / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere

2.2: 12.5 h / -78 - 20 °C / Inert atmosphere

2.3: Inert atmosphere

3.1: Grubbs catalyst first generation / dichloromethane / 24 h

4.1: tetrahydrofuran / 4 h / 0 - 20 °C / Inert atmosphere

5.1: sodium perborate tetrahydrate / tetrahydrofuran; water / 15 h / 20 °C / Inert atmosphere

6.1: 1H-imidazole / dichloromethane / 0.5 h / -10 - 0 °C

7.1: tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide / dichloromethane / 4 h / 0 - 20 °C / Inert atmosphere; Molecular sieve

8.1: pyridine; iodine / dichloromethane / 8.25 h / 0 - 20 °C / Inert atmosphere

With pyridine; 1H-imidazole; Grubbs catalyst first generation; sodium periodate; n-butyllithium; tetrapropylammonium perruthennate; sodium perborate tetrahydrate; iodine; 4-methylmorpholine N-oxide; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; water;

DOI:10.1021/ol300667q

upstream raw materials:

(3aS,4S,6aR)-4,6a-dihydro-6-(2-hydroxyethyl)-2,2-dimethyl-3aH-cyclopenta[d][1,3]dioxol-4-ol

(3aS,4S,6aR)-2,2-dimethyl-6-vinyl-3a,6a-dihydro-4H-cyclopenta[d][1,3]dioxol-4-ol

(1S,4R,5S)-3-[2-(tert-butyldiphenylsilyloxy)ethyl]-4,5-(O-isopropylidenedioxy)cyclopent-2⁽³⁾en-1-ol(1S,4R,5S)-3-[2-(tert-butyldiphenylsilyloxy)ethyl]-4,5-(O-isopropylidenedioxy)cyclopent-2⁽³⁾en-1-ol

(2R,3R)-2,3-(O-isopropylidenedioxy)-4-[2-(tert-butyldiphenylsilyloxy)ethyl]-4-cyclopenten-1-one

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