(1S,2R,3R,4R)-1,4-di-O-benzoyl-2-(tert-butyldiphenylsilyloxymethyl)-3-(4-methoxycarbonylbutyl)cyclopentane-1,4-diol

Base Information

Chemical Name:(1S,2R,3R,4R)-1,4-di-O-benzoyl-2-(tert-butyldiphenylsilyloxymethyl)-3-(4-methoxycarbonylbutyl)cyclopentane-1,4-diol
CAS No.:213777-24-3
Molecular Formula:C₄₂H₄₈O₇Si
Molecular Weight:692.924
Hs Code.:

Synonyms:(1S,2R,3R,4R)-1,4-di-O-benzoyl-2-(tert-butyldiphenylsilyloxymethyl)-3-(4-methoxycarbonylbutyl)cyclopentane-1,4-diol

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Chemical Property of (1S,2R,3R,4R)-1,4-di-O-benzoyl-2-(tert-butyldiphenylsilyloxymethyl)-3-(4-methoxycarbonylbutyl)cyclopentane-1,4-diol

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Technology Process of (1S,2R,3R,4R)-1,4-di-O-benzoyl-2-(tert-butyldiphenylsilyloxymethyl)-3-(4-methoxycarbonylbutyl)cyclopentane-1,4-diol

There total 6 articles about (1S,2R,3R,4R)-1,4-di-O-benzoyl-2-(tert-butyldiphenylsilyloxymethyl)-3-(4-methoxycarbonylbutyl)cyclopentane-1,4-diol 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:

: 213777-20-9
(1S,2R,3R,4R)-2-(tert-butyldiphenylsilyloxymethyl)-3-[(Z)-5,5-bis(isopropyloxy)pent-2-enyl]-1,4-di-O-(triethylsilyl)cyclopentane-1,4-diol

: 213777-24-3
(1S,2R,3R,4R)-1,4-di-O-benzoyl-2-(tert-butyldiphenylsilyloxymethyl)-3-(4-methoxycarbonylbutyl)cyclopentane-1,4-diol

Guidance literature:: Multi-step reaction with 5 steps

1: 95 percent / H₂ / Pd/C / 4 h / 2068.65 Torr

2: 91 percent / pyridine / 2 h / 20 °C

3: FeCl₃ / H₂O; acetone / 2 h / 20 °C

4: m-CPBA / tetrahydrofuran / 12 h / 20 °C

5: 53 mg / diethyl ether

With pyridine; hydrogen; iron(III) chloride; 3-chloro-benzenecarboperoxoic acid; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; water; acetone;
DOI:10.1002/1099-0690(200102)2001:4<809::AID-EJOC809>3.0.CO;2-6

Reference yield:

: 213777-18-5
(1S,2S,3R,4R)-1,4-Bis(triethylsilyloxy)-3-(methoxycarbonylmethyl)-2-tert-butyldiphenylsilyloxymethylcyclopentane

: 213777-24-3
(1S,2R,3R,4R)-1,4-di-O-benzoyl-2-(tert-butyldiphenylsilyloxymethyl)-3-(4-methoxycarbonylbutyl)cyclopentane-1,4-diol

Guidance literature:: Multi-step reaction with 7 steps

1.1: 93 percent / DIBAL-H / toluene / 0.5 h / -78 °C

2.1: NaN(SiMe₃)2 / tetrahydrofuran / 2 h / -80 °C

2.2: 83 percent / tetrahydrofuran / 2 h / -80 - 20 °C

3.1: 95 percent / H₂ / Pd/C / 4 h / 2068.65 Torr

4.1: 91 percent / pyridine / 2 h / 20 °C

5.1: FeCl₃ / H₂O; acetone / 2 h / 20 °C

6.1: m-CPBA / tetrahydrofuran / 12 h / 20 °C

7.1: 53 mg / diethyl ether

With pyridine; hydrogen; sodium hexamethyldisilazane; iron(III) chloride; diisobutylaluminium hydride; 3-chloro-benzenecarboperoxoic acid; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; water; acetone; toluene; 2.2: Wittig reaction;
DOI:10.1002/1099-0690(200102)2001:4<809::AID-EJOC809>3.0.CO;2-6

Reference yield:

: 213777-19-6
(1S,2R,3R,4R)-2-(tert-butyldiphenylsilyloxymethyl)-3-(formylmethyl)-1,4-bis-O-(triethylsilyl)cyclopentane-1,4-diol

: 213777-24-3
(1S,2R,3R,4R)-1,4-di-O-benzoyl-2-(tert-butyldiphenylsilyloxymethyl)-3-(4-methoxycarbonylbutyl)cyclopentane-1,4-diol

Guidance literature:: Multi-step reaction with 6 steps

1.1: NaN(SiMe₃)2 / tetrahydrofuran / 2 h / -80 °C

1.2: 83 percent / tetrahydrofuran / 2 h / -80 - 20 °C

2.1: 95 percent / H₂ / Pd/C / 4 h / 2068.65 Torr

3.1: 91 percent / pyridine / 2 h / 20 °C

4.1: FeCl₃ / H₂O; acetone / 2 h / 20 °C

5.1: m-CPBA / tetrahydrofuran / 12 h / 20 °C

6.1: 53 mg / diethyl ether

With pyridine; hydrogen; sodium hexamethyldisilazane; iron(III) chloride; 3-chloro-benzenecarboperoxoic acid; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; water; acetone; 1.2: Wittig reaction;
DOI:10.1002/1099-0690(200102)2001:4<809::AID-EJOC809>3.0.CO;2-6