(+)-(1S,2R,4R,6R)-2,4-Bis(benzyloxy)-1,6-epoxycyclohexane

Base Information

• Chemical Name: (+)-(1S,2R,4R,6R)-2,4-Bis(benzyloxy)-1,6-epoxycyclohexane
• CAS No.: 163878-18-0
• Molecular Formula: C₂₀H₂₂O₃
• Molecular Weight: 310.393
• Mol file: 163878-18-0.mol

Synonyms:(+)-(1S,2R,4R,6R)-2,4-Bis(benzyloxy)-1,6-epoxycyclohexane

Chemical Property of (+)-(1S,2R,4R,6R)-2,4-Bis(benzyloxy)-1,6-epoxycyclohexane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+)-(1S,2R,4R,6R)-2,4-Bis(benzyloxy)-1,6-epoxycyclohexane

There total 15 articles about (+)-(1S,2R,4R,6R)-2,4-Bis(benzyloxy)-1,6-epoxycyclohexane 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: 95.0%

benzyl bromide (100-39-0) + (+)-(1S,2R,4R,6R)-4-Benzyloxy-1,6-epoxycyclohexan-2-ol (140363-96-8) → (+)-(1S,2R,4R,6R)-2,4-Bis(benzyloxy)-1,6-epoxycyclohexane (163878-18-0)

Guidance literature:

With potassium hydride; In tetrahydrofuran;

DOI:10.1016/S0040-4039(96)02229-0

Reference yield: 69.0%

benzyl bromide (100-39-0) + (1R,3R,4R,5S)-4,5-epoxycyclohexane-1,3-diol (406461-00-5) → (+)-(1S,2R,4R,6R)-2,4-Bis(benzyloxy)-1,6-epoxycyclohexane (163878-18-0)

Guidance literature:

With tetra-(n-butyl)ammonium iodide; sodium hydride; In tetrahydrofuran; at 20 ℃; for 24h;

DOI:10.1039/b107567p

Reference yield:

(-)-(1R,2R,4S,6R)-1,2-Cyclohexylidenedioxy-4-(tert-butyldiphenylsilyl)-6-(4'-methylphenylsulfonyloxy)cyclohexane (186703-34-4) → (+)-(1S,2R,4R,6R)-2,4-Bis(benzyloxy)-1,6-epoxycyclohexane (163878-18-0)

Guidance literature:

Multi-step reaction with 5 steps

1: 100 percent / TBAF / tetrahydrofuran / 16 h / 20 °C

2: 80 percent / NaH / dimethylformamide / 12 h / -50 - 20 °C

3: 78 percent / TFA / methanol / 48 h / 20 °C

4: 90 percent / K₂CO₃ / methanol / 0.5 h / 20 °C

5: 93 percent / KH / tetrahydrofuran / 3 h / 20 °C

With tetrabutyl ammonium fluoride; potassium hydride; sodium hydride; potassium carbonate; trifluoroacetic acid; In tetrahydrofuran; methanol; N,N-dimethyl-formamide; 1: Substitution / 2: Alkylation / 3: Ring cleavage / 4: Epoxidation / 5: Alkylation;

DOI:10.1039/a909292g

upstream raw materials:

benzyl bromide

(+)-(1S,2R,4R,6R)-4-Benzyloxy-1,6-epoxycyclohexan-2-ol

(1R,3R,4R,5S)-4,5-epoxycyclohexane-1,3-diol

(2S,3S,5S)-2,3-epoxy-5-hydroxycyclohexanone

Downstream raw materials:

(-)-(1R,2R,4S,6S,2'S)-2,4-Bis(benzyloxy)-6-(1'-benzyloxy-3'-phenylpropan-2-yloxy)cyclohexanol

(-)-(1R,2R,4S,6S,2'R)-2,4-Bis(benzyloxy)-6-(1'-benzyloxy-3'-phenylpropan-2-yloxy)cyclohexanol

(-)-(1S,2R,4S,6R)-2,4,6-tris(benzyloxy)cyclohexanol

(-)-(1S,2R,4S,6R)-1-(Diphenoxyphosphoryloxy)-2,4-bis(benzyloxy)-6-propyloxycyclohexe