tert-Butyl-diphenyl-((3R,5S,7R,9S)-3,5,7,9-tetrakis-methoxymethoxy-10-(S)-oxiranyl-decyloxy)-silane

Base Information

• Chemical Name: tert-Butyl-diphenyl-((3R,5S,7R,9S)-3,5,7,9-tetrakis-methoxymethoxy-10-(S)-oxiranyl-decyloxy)-silane
• CAS No.: 126455-66-1
• Molecular Formula: C₃₆H₅₈O₁₀Si
• Molecular Weight: 678.936
• Mol file: 126455-66-1.mol

Synonyms:

Chemical Property of tert-Butyl-diphenyl-((3R,5S,7R,9S)-3,5,7,9-tetrakis-methoxymethoxy-10-(S)-oxiranyl-decyloxy)-silane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-Butyl-diphenyl-((3R,5S,7R,9S)-3,5,7,9-tetrakis-methoxymethoxy-10-(S)-oxiranyl-decyloxy)-silane

There total 14 articles about tert-Butyl-diphenyl-((3R,5S,7R,9S)-3,5,7,9-tetrakis-methoxymethoxy-10-(S)-oxiranyl-decyloxy)-silane 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:

tert-Butyl-[(3R,5S,7R,9S)-10-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-3,5,7,9-tetrakis-methoxymethoxy-decyloxy]-diphenyl-silane (126396-23-4) → tert-Butyl-diphenyl-((3R,5S,7R,9S)-3,5,7,9-tetrakis-methoxymethoxy-10-(S)-oxiranyl-decyloxy)-silane (126396-24-5,126455-66-1)

Guidance literature:

Multi-step reaction with 2 steps

1: pyridinium p-toluenesulfonate (PPTS) / methanol / 45 °C

With pyridinium p-toluenesulfonate; In methanol;

DOI:10.1016/S0040-4039(00)99366-3

Reference yield:

(2S)-O-(tert-butyldiphenylsilyl)-1,2-epoxybutan-4-ol (125975-53-3,147220-48-2,116996-54-4) → tert-Butyl-diphenyl-((3R,5S,7R,9S)-3,5,7,9-tetrakis-methoxymethoxy-10-(S)-oxiranyl-decyloxy)-silane (126396-24-5,126455-66-1)

Guidance literature:

Multi-step reaction with 12 steps

1: 93 percent / n-BuLi / tetrahydrofuran / -20 °C

2: 81 percent / MeI-CaCO₃ / acetonitrile; H₂O

3: LiAlH(OtBu)3-LiI / diethyl ether / 1 h / -78 °C / 1,3-asymmetric reduction of the β-alkoxy β'-hydroxy ketone with variation of reagent and temperature

4: iPr₂EtN / CH₂Cl₂ / 0 °C

5: pyridinium p-toluenesulfonate (PPTS) / methanol / 45 °C

7: 90 percent / n-BuLi / tetrahydrofuran / -20 °C

8: 90 percent / MeI-CaCO₃ / acetonitrile; H₂O

9: 89 percent Spectr_. / LiAlH(OtBu)3-LiI / diethyl ether / 1 h / 0 °C

10: iPr₂EtN / CH₂Cl₂ / 0 °C

11: pyridinium p-toluenesulfonate (PPTS) / methanol / 45 °C

With n-butyllithium; MeI-CaCO₃; pyridinium p-toluenesulfonate; lithium tri-t-butoxyaluminum hydride; N-ethyl-N,N-diisopropylamine; lithium iodide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; acetonitrile;

DOI:10.1016/S0040-4039(00)99366-3

Reference yield:

((3R,5S)-3,5-Bis-methoxymethoxy-6-(S)-oxiranyl-hexyloxy)-tert-butyl-diphenyl-silane (127725-30-8) → tert-Butyl-diphenyl-((3R,5S,7R,9S)-3,5,7,9-tetrakis-methoxymethoxy-10-(S)-oxiranyl-decyloxy)-silane (126396-24-5,126455-66-1)

Guidance literature:

Multi-step reaction with 6 steps

1: 90 percent / n-BuLi / tetrahydrofuran / -20 °C

2: 90 percent / MeI-CaCO₃ / acetonitrile; H₂O

3: 89 percent Spectr_. / LiAlH(OtBu)3-LiI / diethyl ether / 1 h / 0 °C

4: iPr₂EtN / CH₂Cl₂ / 0 °C

5: pyridinium p-toluenesulfonate (PPTS) / methanol / 45 °C

With n-butyllithium; MeI-CaCO₃; pyridinium p-toluenesulfonate; lithium tri-t-butoxyaluminum hydride; N-ethyl-N,N-diisopropylamine; lithium iodide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; acetonitrile;

DOI:10.1016/S0040-4039(00)99366-3

upstream raw materials:

tert-Butyl-[(3R,5S,7R,9S)-10-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-3,5,7,9-tetrakis-methoxymethoxy-decyloxy]-diphenyl-silane

(2S)-O-(tert-butyldiphenylsilyl)-1,2-epoxybutan-4-ol

((3R,5S)-3,5-Bis-methoxymethoxy-6-(S)-oxiranyl-hexyloxy)-tert-butyl-diphenyl-silane

(4R,6R,8R)-10-(tert-Butyl-diphenyl-silanyloxy)-1-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-4-hydroxy-6,8-bis-methoxymethoxy-decan-2-one

Downstream raw materials:

(2S,4R,6R,8S,10S,12R)-14-(tert-Butyl-diphenyl-silanyloxy)-1-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-6,8,10,12-tetrakis-methoxymethoxy-tetradecane-2,4-diol

(2S,4R,6R,8S,10S,12R)-14-(tert-Butyl-diphenyl-silanyloxy)-1-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-6,8,10,12-tetrakis-methoxymethoxy-tetradecane-2,4-diol

(2R,4R,6R,8S,10S,12R)-14-(tert-Butyl-diphenyl-silanyloxy)-1-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-6,8,10,12-tetrakis-methoxymethoxy-tetradecane-2,4-diol

(2R,4R,6R,8S,10S,12R)-14-(tert-Butyl-diphenyl-silanyloxy)-1-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-6,8,10,12-tetrakis-methoxymethoxy-tetradecane-2,4-diol