((1R,2R,4R,5R)-4,5-bis(benzyloxy)-2-((tert-butyldimethylsilyloxy)methyl)cyclohexyl)methanol

Base Information

• Chemical Name: ((1R,2R,4R,5R)-4,5-bis(benzyloxy)-2-((tert-butyldimethylsilyloxy)methyl)cyclohexyl)methanol
• CAS No.: 956006-05-6
• Molecular Formula: C₂₈H₄₂O₄Si
• Molecular Weight: 470.725
• Mol file: 956006-05-6.mol

Synonyms:((1R,2R,4R,5R)-4,5-bis(benzyloxy)-2-((tert-butyldimethylsilyloxy)methyl)cyclohexyl)methanol

Chemical Property of ((1R,2R,4R,5R)-4,5-bis(benzyloxy)-2-((tert-butyldimethylsilyloxy)methyl)cyclohexyl)methanol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ((1R,2R,4R,5R)-4,5-bis(benzyloxy)-2-((tert-butyldimethylsilyloxy)methyl)cyclohexyl)methanol

There total 5 articles about ((1R,2R,4R,5R)-4,5-bis(benzyloxy)-2-((tert-butyldimethylsilyloxy)methyl)cyclohexyl)methanol 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: 93.0%

((1R,2R,4R,5R)-4,5-bis(benzyloxy)-2-(hydroxymethyl)cyclohexyl)methanol (956006-36-3) + tert-butyldimethylsilyl chloride (18162-48-6) → ((1R,2R,4R,5R)-4,5-bis(benzyloxy)-2-((tert-butyldimethylsilyloxy)methyl)cyclohexyl)methanol (956006-05-6)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; hexane; at 20 ℃; for 12h;

DOI:10.1021/ol7017938

Reference yield:

(1R,2R,4R,5R)-bis((1S,2R,5S)-2-isopropyl-5-methylcyclohexyl) 4-(benzyloxy)-5-hydroxycyclohexane-1,2-dicarboxylate (956006-35-2) → ((1R,2R,4R,5R)-4,5-bis(benzyloxy)-2-((tert-butyldimethylsilyloxy)methyl)cyclohexyl)methanol (956006-05-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 99 percent / TfOH / CH₂Cl₂; cyclohexane / 24 h / 20 °C

2: 85 percent / LiAlH₄ / diethyl ether / 12 h / -78 - 20 °C

3: 93 percent / nBuLi / tetrahydrofuran; hexane / 12 h / 20 °C

With lithium aluminium tetrahydride; n-butyllithium; trifluorormethanesulfonic acid; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; cyclohexane;

DOI:10.1021/ol7017938

Reference yield:

(1R,2R,4R,5R)-bis((1S,2R,5S)-2-isopropyl-5-methylcyclohexyl) 4,5-bis(benzyloxy)cyclohexane-1,2-dicarboxylate (956006-03-4) → ((1R,2R,4R,5R)-4,5-bis(benzyloxy)-2-((tert-butyldimethylsilyloxy)methyl)cyclohexyl)methanol (956006-05-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 85 percent / LiAlH₄ / diethyl ether / 12 h / -78 - 20 °C

2: 93 percent / nBuLi / tetrahydrofuran; hexane / 12 h / 20 °C

With lithium aluminium tetrahydride; n-butyllithium; In tetrahydrofuran; diethyl ether; hexane;

DOI:10.1021/ol7017938

upstream raw materials:

((1R,2R,4R,5R)-4,5-bis(benzyloxy)-2-(hydroxymethyl)cyclohexyl)methanol

tert-butyldimethylsilyl chloride

(1S,3R,4R,6R)-3-((1S,2R,5S)-2-isopropyl-5-methylcyclohexyl) 4-((1S,2R,5S)-2-isopropyl-5-methylcyclohexyl) 7-oxabicyclo[4.1.0]heptane-3,4-dicarboxylate

(1R,2R,4R,5R)-bis((1S,2R,5S)-2-isopropyl-5-methylcyclohexyl) 4-(benzyloxy)-5-hydroxycyclohexane-1,2-dicarboxylate

Downstream raw materials:

N-((S)-1-((1R,2R,4R,5R)-4,5-bis(benzyloxy)-2-(hydroxymethyl)cyclohexyl)-3-(tert-butyldimethylsilyloxy)propan-2-yl)-2,2,2-trifluoroacetamide

1-((3S,4aR,6R,7R,8aR)-6,7-bis(benzyloxy)-3-((tert-butyldimethylsilyloxy)methyl)octahydroisoquinolin-2-(1H)-yl)-2,2,2-trifluoroethanone

2-((2S,4R,5R)-2-((tert-butyldimethylsilyloxy)methyl)-5-(2-hydroxyethyl)-1-(2,2,2-trifluoroacetyl)piperidin-4-yl)ethyl benzoate

2-((3R,4R,6S)-6-((tert-butyldimethylsilyloxy)methyl)-4-(2-hydroxyethyl)-1-(2,2,2-trifluoroacetyl)piperidin-3-yl)ethyl benzoate