(2R,3R)-1-(3-isopropyl-6-methylcyclohexa-1,5-dienyl)-5-(trimethylsilyl)pent-4-yne-1,2-diol

Base Information

Chemical Name:(2R,3R)-1-(3-isopropyl-6-methylcyclohexa-1,5-dienyl)-5-(trimethylsilyl)pent-4-yne-1,2-diol
CAS No.:294674-47-8
Molecular Formula:C₁₈H₃₀O₂Si
Molecular Weight:306.521
Hs Code.:

Synonyms:(2R,3R)-1-(3-isopropyl-6-methylcyclohexa-1,5-dienyl)-5-(trimethylsilyl)pent-4-yne-1,2-diol

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Chemical Property of (2R,3R)-1-(3-isopropyl-6-methylcyclohexa-1,5-dienyl)-5-(trimethylsilyl)pent-4-yne-1,2-diol

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Technology Process of (2R,3R)-1-(3-isopropyl-6-methylcyclohexa-1,5-dienyl)-5-(trimethylsilyl)pent-4-yne-1,2-diol

There total 8 articles about (2R,3R)-1-(3-isopropyl-6-methylcyclohexa-1,5-dienyl)-5-(trimethylsilyl)pent-4-yne-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:

: (R)-1-((R)-3-Isopropyl-6-methyl-cyclohexa-1,5-dienyl)-2-(1-methoxy-1-methyl-ethoxy)-5-trimethylsilanyl-pent-4-yn-1-ol

: 294674-47-8
(2R,3R)-1-(3-isopropyl-6-methylcyclohexa-1,5-dienyl)-5-(trimethylsilyl)pent-4-yne-1,2-diol

Guidance literature:: With pyridinium p-toluenesulfonate; In methanol;
DOI:10.1021/ja00146a028

Reference yield:

: 54655-07-1
lithium trimethylsilylacetylenide

: 294674-47-8
(2R,3R)-1-(3-isopropyl-6-methylcyclohexa-1,5-dienyl)-5-(trimethylsilyl)pent-4-yne-1,2-diol

Guidance literature:: Multi-step reaction with 6 steps

1.1: 61 percent / BF₃*Et₂O / tetrahydrofuran; hexane

2.1: 97 percent / pyridinium p-toluenesulfonate / 5 h / 23 °C

3.1: 89 percent / i-Bu₂AlH / toluene / 0.5 h / -78 °C

4.1: 84 percent / tetra-n-propylammonium perruthenate; N-methylmorpholine N-oxide; 4A molecular sieves / CH₂Cl₂ / 0.25 h / 20 °C

5.1: t-butyllithium / tetrahydrofuran; hexane / -78 °C

5.2: tetrahydrofuran; hexane / -78 - -23 °C

6.1: pyridinium p-toluenesulfonate / methanol / 4 h / 20 °C

With tetrapropylammonium perruthennate; 4 A molecular sieve; boron trifluoride diethyl etherate; tert.-butyl lithium; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; 4-methylmorpholine N-oxide; In tetrahydrofuran; methanol; hexane; dichloromethane; toluene;
DOI:10.1021/ja016351a

Reference yield:

: 170309-23-6
2,2-dimethylpropionic acid (2R)-2-(1-methoxy-1-methylethoxy)-5-(trimethylsilyl)pent-4-ynyl ester

: 294674-47-8
(2R,3R)-1-(3-isopropyl-6-methylcyclohexa-1,5-dienyl)-5-(trimethylsilyl)pent-4-yne-1,2-diol

Guidance literature:: Multi-step reaction with 4 steps

1.1: 89 percent / i-Bu₂AlH / toluene / 0.5 h / -78 °C

2.1: 84 percent / tetra-n-propylammonium perruthenate; N-methylmorpholine N-oxide; 4A molecular sieves / CH₂Cl₂ / 0.25 h / 20 °C

3.1: t-butyllithium / tetrahydrofuran; hexane / -78 °C

3.2: tetrahydrofuran; hexane / -78 - -23 °C

4.1: pyridinium p-toluenesulfonate / methanol / 4 h / 20 °C

With tetrapropylammonium perruthennate; 4 A molecular sieve; tert.-butyl lithium; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; 4-methylmorpholine N-oxide; In tetrahydrofuran; methanol; hexane; dichloromethane; toluene;
DOI:10.1021/ja016351a