(E)-(1S,2S)-7-(tert-Butyl-dimethyl-silanyloxy)-1-{(2R,4S,5S,6R)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-4-methoxymethoxy-5-methyl-tetrahydro-pyran-2-yl}-hept-3-ene-1,2-diol

Base Information

Chemical Name:(E)-(1S,2S)-7-(tert-Butyl-dimethyl-silanyloxy)-1-{(2R,4S,5S,6R)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-4-methoxymethoxy-5-methyl-tetrahydro-pyran-2-yl}-hept-3-ene-1,2-diol
CAS No.:859845-20-8
Molecular Formula:C₃₉H₆₄O₇Si₂
Molecular Weight:701.104
Hs Code.:

(E)-(1S,2S)-7-(tert-Butyl-dimethyl-silanyloxy)-1-{(2R,4S,5S,6R)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-4-methoxymethoxy-5-methyl-tetrahydro-pyran-2-yl}-hept-3-ene-1,2-diol

Synonyms:(E)-(1S,2S)-7-(tert-Butyl-dimethyl-silanyloxy)-1-{(2R,4S,5S,6R)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-4-methoxymethoxy-5-methyl-tetrahydro-pyran-2-yl}-hept-3-ene-1,2-diol

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Chemical Property of (E)-(1S,2S)-7-(tert-Butyl-dimethyl-silanyloxy)-1-{(2R,4S,5S,6R)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-4-methoxymethoxy-5-methyl-tetrahydro-pyran-2-yl}-hept-3-ene-1,2-diol

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Technology Process of (E)-(1S,2S)-7-(tert-Butyl-dimethyl-silanyloxy)-1-{(2R,4S,5S,6R)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-4-methoxymethoxy-5-methyl-tetrahydro-pyran-2-yl}-hept-3-ene-1,2-diol

There total 16 articles about (E)-(1S,2S)-7-(tert-Butyl-dimethyl-silanyloxy)-1-{(2R,4S,5S,6R)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-4-methoxymethoxy-5-methyl-tetrahydro-pyran-2-yl}-hept-3-ene-1,2-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: 88.0%

: 859844-89-6
(2R,3S,4S,6R)-6-[(E)-(1R,2S)-1,2-Bis-benzyloxy-7-(tert-butyl-dimethyl-silanyloxy)-hept-3-enyl]-2-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-4-methoxymethoxy-3-methyl-tetrahydro-pyran

: 859845-20-8
(E)-(1S,2S)-7-(tert-Butyl-dimethyl-silanyloxy)-1-{(2R,4S,5S,6R)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-4-methoxymethoxy-5-methyl-tetrahydro-pyran-2-yl}-hept-3-ene-1,2-diol

Guidance literature:: With lithium 4,4′-di(tert-butyl)biphenyl; In tetrahydrofuran; at -78 - -40 ℃;
DOI:10.1021/ol051119l

Reference yield:

: 859845-15-1
(2R,3R)-5-(tert-Butyl-diphenyl-silanyloxy)-2-methyl-3-triethylsilanyloxy-pentan-1-ol

: 859845-20-8
(E)-(1S,2S)-7-(tert-Butyl-dimethyl-silanyloxy)-1-{(2R,4S,5S,6R)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-4-methoxymethoxy-5-methyl-tetrahydro-pyran-2-yl}-hept-3-ene-1,2-diol

Guidance literature:: Multi-step reaction with 10 steps

1.1: 98 percent / Huenigs' base; SO₃*Py / CH₂Cl₂; dimethylsulfoxide / 20 °C

2.1: dicyclohexylboron chloride; Et₃N / diethyl ether; hexane / 1.5 h / 0 °C

2.2: 27 percent / diethyl ether; hexane / -78 - -45 °C

3.1: 92 percent / PPh₃*HBr / methanol; tetrahydrofuran / 7 h / 0 °C

4.1: 95 percent / SO₃*Py; Et₃N / CH₂Cl₂; dimethylsulfoxide / 20 °C

5.1: 94 percent / L-selectride / tetrahydrofuran / -78 °C

6.1: 93 percent / Et₃SiH; TMSOTf / CH₂Cl₂ / -78 °C

7.1: 100 percent / 2,6-lutidine / acetonitrile / 20 °C

8.1: Cp₂ZrHCl / CH₂Cl₂ / 1.5 h / 20 °C

8.2: 100 percent / I₂ / CH₂Cl₂ / 0.5 h / 20 °C

9.1: t-BuLi; 9-BBN*OMe / diethyl ether; pentane; hexane / -78 - 20 °C

9.2: 100 percent / aq. Cs₂CO₃; DMF / Pd(dppf)2Cl₂ / diethyl ether; pentane; hexane / 20 °C

10.1: 88 percent / LiDBB / tetrahydrofuran / -78 - -40 °C

With 2,6-dimethylpyridine; triethylsilane; Schwartz's reagent; lithium 4,4′-di(tert-butyl)biphenyl; pyridine-SO₃ complex; trimethylsilyl trifluoromethanesulfonate; dicyclohexylboron chloride; tert.-butyl lithium; triphenylphosphine hydrobromide; L-Selectride; triethylamine; N-ethyl-N,N-diisopropylamine; 9-methoxy-9-BBN; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; dimethyl sulfoxide; acetonitrile; pentane; 9.2: Suzuki-Miyaura coupling;
DOI:10.1021/ol051119l

Reference yield:

: 859844-79-4
(2S,3R)-5-(tert-Butyl-diphenyl-silanyloxy)-2-methyl-3-triethylsilanyloxy-pentanal

: 859845-20-8
(E)-(1S,2S)-7-(tert-Butyl-dimethyl-silanyloxy)-1-{(2R,4S,5S,6R)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-4-methoxymethoxy-5-methyl-tetrahydro-pyran-2-yl}-hept-3-ene-1,2-diol

Guidance literature:: Multi-step reaction with 9 steps

1.1: dicyclohexylboron chloride; Et₃N / diethyl ether; hexane / 1.5 h / 0 °C

1.2: 27 percent / diethyl ether; hexane / -78 - -45 °C

2.1: 92 percent / PPh₃*HBr / methanol; tetrahydrofuran / 7 h / 0 °C

3.1: 95 percent / SO₃*Py; Et₃N / CH₂Cl₂; dimethylsulfoxide / 20 °C

4.1: 94 percent / L-selectride / tetrahydrofuran / -78 °C

5.1: 93 percent / Et₃SiH; TMSOTf / CH₂Cl₂ / -78 °C

6.1: 100 percent / 2,6-lutidine / acetonitrile / 20 °C

7.1: Cp₂ZrHCl / CH₂Cl₂ / 1.5 h / 20 °C

7.2: 100 percent / I₂ / CH₂Cl₂ / 0.5 h / 20 °C

8.1: t-BuLi; 9-BBN*OMe / diethyl ether; pentane; hexane / -78 - 20 °C

8.2: 100 percent / aq. Cs₂CO₃; DMF / Pd(dppf)2Cl₂ / diethyl ether; pentane; hexane / 20 °C

9.1: 88 percent / LiDBB / tetrahydrofuran / -78 - -40 °C

With 2,6-dimethylpyridine; triethylsilane; Schwartz's reagent; lithium 4,4′-di(tert-butyl)biphenyl; pyridine-SO₃ complex; trimethylsilyl trifluoromethanesulfonate; dicyclohexylboron chloride; tert.-butyl lithium; triphenylphosphine hydrobromide; L-Selectride; triethylamine; 9-methoxy-9-BBN; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; dimethyl sulfoxide; acetonitrile; pentane; 8.2: Suzuki-Miyaura coupling;
DOI:10.1021/ol051119l