(1S,2R,3R,4R)-2-(tert-butyldiphenylsilyloxymethyl)-1,4-bis-O-(triethylsilyl)-3-[(Z)-7-(methoxycarbonyl)hept-2-enyl]cyclopentane-1,4-diol

Base Information

Chemical Name:(1S,2R,3R,4R)-2-(tert-butyldiphenylsilyloxymethyl)-1,4-bis-O-(triethylsilyl)-3-[(Z)-7-(methoxycarbonyl)hept-2-enyl]cyclopentane-1,4-diol
CAS No.:534584-74-2
Molecular Formula:C₄₃H₇₂O₅Si₃
Molecular Weight:753.298
Hs Code.:

Synonyms:(1S,2R,3R,4R)-2-(tert-butyldiphenylsilyloxymethyl)-1,4-bis-O-(triethylsilyl)-3-[(Z)-7-(methoxycarbonyl)hept-2-enyl]cyclopentane-1,4-diol

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Chemical Property of (1S,2R,3R,4R)-2-(tert-butyldiphenylsilyloxymethyl)-1,4-bis-O-(triethylsilyl)-3-[(Z)-7-(methoxycarbonyl)hept-2-enyl]cyclopentane-1,4-diol

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Technology Process of (1S,2R,3R,4R)-2-(tert-butyldiphenylsilyloxymethyl)-1,4-bis-O-(triethylsilyl)-3-[(Z)-7-(methoxycarbonyl)hept-2-enyl]cyclopentane-1,4-diol

There total 6 articles about (1S,2R,3R,4R)-2-(tert-butyldiphenylsilyloxymethyl)-1,4-bis-O-(triethylsilyl)-3-[(Z)-7-(methoxycarbonyl)hept-2-enyl]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: 70.0%

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

: [5-(methoxycarbonyl)pentyl]triphenylphosphonium iodide

: 534584-74-2
(1S,2R,3R,4R)-2-(tert-butyldiphenylsilyloxymethyl)-1,4-bis-O-(triethylsilyl)-3-[(Z)-7-(methoxycarbonyl)hept-2-enyl]cyclopentane-1,4-diol

Guidance literature:: With potassium hexamethylsilazane; In tetrahydrofuran; at -80 - 20 ℃; for 2h;
DOI:10.1016/S0040-4039(03)00171-0

Reference yield:

: 4547-43-7
methyl 6-hydroxycaproate

: 534584-74-2
(1S,2R,3R,4R)-2-(tert-butyldiphenylsilyloxymethyl)-1,4-bis-O-(triethylsilyl)-3-[(Z)-7-(methoxycarbonyl)hept-2-enyl]cyclopentane-1,4-diol

Guidance literature:: Multi-step reaction with 3 steps

1.1: 61 percent / triphenylphosphine; iodine; imidazole / CH₂Cl₂ / -10 - 20 °C

2.1: 98 percent / K₂CO₃ / acetonitrile / 48 h / Heating

3.1: KHMDS / tetrahydrofuran; toluene / -80 - -40 °C

3.2: 70 percent / tetrahydrofuran; toluene / 2 h / -80 - 20 °C

With 1H-imidazole; iodine; potassium hexamethylsilazane; potassium carbonate; triphenylphosphine; In tetrahydrofuran; dichloromethane; toluene; acetonitrile; 3.2: Wittig reaction;
DOI:10.1021/jo035638i

Reference yield:

: 14273-91-7
methyl 6-iodohexanoate

: 534584-74-2
(1S,2R,3R,4R)-2-(tert-butyldiphenylsilyloxymethyl)-1,4-bis-O-(triethylsilyl)-3-[(Z)-7-(methoxycarbonyl)hept-2-enyl]cyclopentane-1,4-diol

Guidance literature:: Multi-step reaction with 2 steps

1.1: 98 percent / K₂CO₃ / acetonitrile / 48 h / Heating

2.1: KHMDS / tetrahydrofuran; toluene / -80 - -40 °C

2.2: 70 percent / tetrahydrofuran; toluene / 2 h / -80 - 20 °C

With potassium hexamethylsilazane; potassium carbonate; In tetrahydrofuran; toluene; acetonitrile; 2.2: Wittig reaction;
DOI:10.1021/jo035638i