(2R,4R,5R,6E,8S,9S,10Z)-2-tert-butyldimethylsiloxy-5-(2-tert-butyldiphenylsiloxyethyl)-9-ethyl-4,5-isopropylidenedioxy-6,10-dodecadiene-1,8,12-triol

Base Information

• Chemical Name: (2R,4R,5R,6E,8S,9S,10Z)-2-tert-butyldimethylsiloxy-5-(2-tert-butyldiphenylsiloxyethyl)-9-ethyl-4,5-isopropylidenedioxy-6,10-dodecadiene-1,8,12-triol
• CAS No.: 943144-75-0
• Molecular Formula: C₄₁H₆₆O₇Si₂
• Molecular Weight: 727.142
• Mol file: 943144-75-0.mol

Synonyms:(2R,4R,5R,6E,8S,9S,10Z)-2-tert-butyldimethylsiloxy-5-(2-tert-butyldiphenylsiloxyethyl)-9-ethyl-4,5-isopropylidenedioxy-6,10-dodecadiene-1,8,12-triol

Chemical Property of (2R,4R,5R,6E,8S,9S,10Z)-2-tert-butyldimethylsiloxy-5-(2-tert-butyldiphenylsiloxyethyl)-9-ethyl-4,5-isopropylidenedioxy-6,10-dodecadiene-1,8,12-triol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,4R,5R,6E,8S,9S,10Z)-2-tert-butyldimethylsiloxy-5-(2-tert-butyldiphenylsiloxyethyl)-9-ethyl-4,5-isopropylidenedioxy-6,10-dodecadiene-1,8,12-triol

There total 22 articles about (2R,4R,5R,6E,8S,9S,10Z)-2-tert-butyldimethylsiloxy-5-(2-tert-butyldiphenylsiloxyethyl)-9-ethyl-4,5-isopropylidenedioxy-6,10-dodecadiene-1,8,12-triol 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: 92.0%

(2Z,4S,5S,6E,8R,9R,11R)-11-tert-butyldimethylsiloxy-8-(2-tert-butyldiphenylsiloxyethyl)-4-ethyl-8,9-isopropylidenedioxy-1,12-bis(4-methoxybenzyloxy)-2,6-dodecadien-5-ol (1040233-95-1) → (2R,4R,5R,6E,8S,9S,10Z)-2-tert-butyldimethylsiloxy-5-(2-tert-butyldiphenylsiloxyethyl)-9-ethyl-4,5-isopropylidenedioxy-6,10-dodecadiene-1,8,12-triol (943144-75-0)

Guidance literature:

With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; water; at 20 ℃; for 1h;

DOI:10.1021/jo8005599

Reference yield: 79.0%

(2R,4R,5R,6E,8S,9S,10Z)-2-tert-butyldimethylsiloxy-5-(2-tert-butyldiphenylsiloxyethyl)-9-ethyl-4,5-isopropylidenedioxy-8,12-bis(4-methoxybenzyloxy)-6,10-dodecadiene (943144-74-9) → (2R,4R,5R,6E,8S,9S,10Z)-2-tert-butyldimethylsiloxy-5-(2-tert-butyldiphenylsiloxyethyl)-9-ethyl-4,5-isopropylidenedioxy-6,10-dodecadiene-1,8,12-triol (943144-75-0)

Guidance literature:

With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; at 20 ℃; for 1h;

DOI:10.1016/j.tetlet.2007.03.152

Reference yield:

(3E)-3-[(3R)-3,4-isopropylidenedioxybutylidene]-2-tetrahydrofuran (943144-61-4) → (2R,4R,5R,6E,8S,9S,10Z)-2-tert-butyldimethylsiloxy-5-(2-tert-butyldiphenylsiloxyethyl)-9-ethyl-4,5-isopropylidenedioxy-6,10-dodecadiene-1,8,12-triol (943144-75-0)

Guidance literature:

Multi-step reaction with 13 steps

1.1: DIBAlH / toluene / 0.33 h / -78 °C

2.1: imidazole / dimethylformamide / 0.5 h / 20 °C

3.1: NaBH₄; CeCl₃*7H₂O / methanol / 0.25 h / -78 °C

4.1: Et₃N / CH₂Cl₂ / 1 h / 0 °C

5.1: 91 percent / (DHQD)2PHAL; K₂OsO₂(OH)4; MeSO₂NH₂ / K₃Fe(CN)6; K₂CO₃ / 2-methyl-propan-2-ol; H₂O / 20 °C

6.1: p-TsOH*H₂O / 0.33 h / 20 °C

7.1: Zn(NO₃)2*6H₂O / acetonitrile / 3 h / 50 °C

8.1: n-Bu₂SnO / toluene / 12 h / Heating

8.2: 76 percent / n-Bu₄NI / toluene / 1.5 h / Heating

9.1: 100 percent / 2,6-lutidine / CH₂Cl₂ / 0.25 h / 20 °C

10.1: K₂CO₃ / methanol / 4 h / 20 °C

11.1: 95 percent / TPAP; NMO; MS 4 Angstroem / CH₂Cl₂ / 2 h / 20 °C

12.1: 14 percent / LiHMDS / tetrahydrofuran / 1 h / -78 - -20 °C

13.1: 79 percent / aq. DDQ / CH₂Cl₂ / 1 h / 20 °C

With 1H-imidazole; 2,6-dimethylpyridine; zinc(II) nitrate; sodium tetrahydroborate; N-methyl-2-indolinone; cerium(III) chloride; tetrapropylammonium perruthennate; potassium dioxotetrahydroxoosmate(VI); methanesulfonamide; MS 4 Angstroem; diisobutylaluminium hydride; di(n-butyl)tin oxide; potassium carbonate; toluene-4-sulfonic acid; 1,4-bis(9-O-dihydroquinidine)phthalazine; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium hexamethyldisilazane; potassium carbonate; potassium hexacyanoferrate(III); In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile; tert-butyl alcohol; 5.1: Sharpless asymmetric dihydroxylation / 12.1: Julia coupling reaction;

DOI:10.1016/j.tetlet.2007.03.152

upstream raw materials:

(2R,4R,5R,6E,8S,9S,10Z)-2-tert-butyldimethylsiloxy-5-(2-tert-butyldiphenylsiloxyethyl)-9-ethyl-4,5-isopropylidenedioxy-8,12-bis(4-methoxybenzyloxy)-6,10-dodecadiene

(2R,3S)-3-ethyl-6-(4-methoxybenzyloxy)-4-hexyne-1,2-diol

(2R,3S)-3-ethyl-1,2-(4-methoxybenzylidenedioxy)-6-(4-methoxybenzyloxy)-4-hexyne

C₂₄H₃₀O₅

Downstream raw materials:

C₄₁H₆₀O₇Si₂

C₄₂H₆₁IO₆Si₂

(5S,6S)-6-[(1E,3R,4R,6R,7Z,9Z)-3-[2-(allyloxycarbonylamino)ethyl]-6-tert-butyldimethylsiloxy-3,4-dihydroxy-10-[(1R,3S)-3-[(6S)-methyloctanoyloxy]cyclohexyl]-1,7,9-decatrienyl]-5-ethyl-5,6-dihydro-2H-pyran-2-one

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