(3R, 4R)-5-((tert-butyldiphenylsilyl)oxy)-4-methylpent-1-yn-3-ol

Base Information

• Chemical Name: (3R, 4R)-5-((tert-butyldiphenylsilyl)oxy)-4-methylpent-1-yn-3-ol
• CAS No.: 216494-43-8
• Molecular Formula: C₂₂H₂₈O₂Si
• Molecular Weight: 352.549
• Mol file: 216494-43-8.mol

Synonyms:(3R, 4R)-5-((tert-butyldiphenylsilyl)oxy)-4-methylpent-1-yn-3-ol

Chemical Property of (3R, 4R)-5-((tert-butyldiphenylsilyl)oxy)-4-methylpent-1-yn-3-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R, 4R)-5-((tert-butyldiphenylsilyl)oxy)-4-methylpent-1-yn-3-ol

There total 7 articles about (3R, 4R)-5-((tert-butyldiphenylsilyl)oxy)-4-methylpent-1-yn-3-ol 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-[(R)-2-((2R,3S)-3-chloromethyl-oxiranyl)-propoxy]-diphenyl-silane (216494-27-8) → (3R, 4R)-5-((tert-butyldiphenylsilyl)oxy)-4-methylpent-1-yn-3-ol (216494-43-8)

Guidance literature:

With lithium diisopropyl amide; In tetrahydrofuran; at -30 ℃;

DOI:10.1021/ja982572d

Reference yield:

((2R,3R)-3-((R)-1-((tert-butyldiphenylsilyl)oxy)propan-2-yl)oxiran-2-yl)methanol (127665-69-4) → (3R, 4R)-5-((tert-butyldiphenylsilyl)oxy)-4-methylpent-1-yn-3-ol (216494-43-8)

Guidance literature:

Multi-step reaction with 2 steps

1: NCS, Ph₃P / CH₂Cl₂ / Heating

2: LDA / tetrahydrofuran / -30 °C

With N-chloro-succinimide; triphenylphosphine; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane;

DOI:10.1021/ja982572d

Reference yield:

(4S)-5-(tert-butyldiphenylsilyloxy)-4-methyl-2-penten-1-ol (127665-68-3) → (3R, 4R)-5-((tert-butyldiphenylsilyl)oxy)-4-methylpent-1-yn-3-ol (216494-43-8)

Guidance literature:

Multi-step reaction with 3 steps

1: titanium(IV) isopropylate; tert.-butylhydroperoxide; diethyl (2S,3S)-tartrate / dichloromethane / 10 h / -20 °C / Molecular sieve

2: tetrachloromethane; sodium hydrogencarbonate; triphenylphosphine / Reflux

3: n-butyllithium / tetrahydrofuran / 3 h / -78 °C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; tetrachloromethane; n-butyllithium; diethyl (2S,3S)-tartrate; sodium hydrogencarbonate; triphenylphosphine; In tetrahydrofuran; dichloromethane;

DOI:10.1016/j.tetlet.2018.08.041

upstream raw materials:

tert-Butyl-[(R)-2-((2R,3S)-3-chloromethyl-oxiranyl)-propoxy]-diphenyl-silane

((2R,3R)-3-((R)-1-((tert-butyldiphenylsilyl)oxy)propan-2-yl)oxiran-2-yl)methanol

(4S)-5-(tert-butyldiphenylsilyloxy)-4-methyl-2-penten-1-ol

(R)-3-[(tert-butyldiphenylsilyl)oxy]-2-methylpropanal

Downstream raw materials:

C₂₈H₄₂O₃Si₂

C₂₈H₄₃IO₃Si₂

Acetic acid (2E,6E)-(1R,4R,5S,11R)-13-hydroxy-1-[(E)-(1R,2R)-1-(4-methoxy-benzyloxy)-2-methyl-hept-3-enyl]-4,11-dimethyl-10-methylene-5-(2-trimethylsilanyl-ethoxymethoxy)-trideca-2,6-dienyl ester

Acetic acid (2E,6E)-(1R,4R,5S,11R)-1-[(E)-(1R,2R)-1-(4-methoxy-benzyloxy)-2-methyl-hept-3-enyl]-4,11-dimethyl-10-methylene-13-oxo-5-(2-trimethylsilanyl-ethoxymethoxy)-trideca-2,6-dienyl ester