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

Base Information

• Chemical Name: ((3R,5S)-3,5-Bis-methoxymethoxy-6-(S)-oxiranyl-hexyloxy)-tert-butyl-diphenyl-silane
• CAS No.: 127725-30-8
• Molecular Formula: C₂₈H₄₂O₆Si
• Molecular Weight: 502.723
• Mol file: 127725-30-8.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 6 articles about ((3R,5S)-3,5-Bis-methoxymethoxy-6-(S)-oxiranyl-hexyloxy)-tert-butyl-diphenyl-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:

(2S)-O-(tert-butyldiphenylsilyl)-1,2-epoxybutan-4-ol (125975-53-3,147220-48-2,116996-54-4) → ((3R,5S)-3,5-Bis-methoxymethoxy-6-(S)-oxiranyl-hexyloxy)-tert-butyl-diphenyl-silane (127725-30-8)

Guidance literature:

Multi-step reaction with 6 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

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:

tert-Butyl-[(3R,5S)-6-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-3,5-bis-methoxymethoxy-hexyloxy]-diphenyl-silane → ((3R,5S)-3,5-Bis-methoxymethoxy-6-(S)-oxiranyl-hexyloxy)-tert-butyl-diphenyl-silane (127725-30-8)

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:

(R)-6-(tert-Butyl-diphenyl-silanyloxy)-1-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-4-hydroxy-hexan-2-one (120341-83-5,127725-23-9) → ((3R,5S)-3,5-Bis-methoxymethoxy-6-(S)-oxiranyl-hexyloxy)-tert-butyl-diphenyl-silane (127725-30-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 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

2: iPr₂EtN / CH₂Cl₂ / 0 °C

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

With pyridinium p-toluenesulfonate; lithium tri-t-butoxyaluminum hydride; N-ethyl-N,N-diisopropylamine; lithium iodide; In methanol; diethyl ether; dichloromethane;

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

upstream raw materials:

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

(2S,4R)-6-(tert-Butyl-diphenyl-silanyloxy)-1-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-hexane-2,4-diol

(R)-6-(tert-Butyl-diphenyl-silanyloxy)-1-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-4-hydroxy-hexan-2-one

(R)-4-(tert-Butyl-diphenyl-silanyloxy)-1-[2-((R)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-[1,3]dithian-2-yl]-butan-2-ol

Downstream raw materials:

(2R,4R,6R)-8-(tert-Butyl-diphenyl-silanyloxy)-1-[2-((R)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-[1,3]dithian-2-yl]-4,6-bis-methoxymethoxy-octan-2-ol

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

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

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