(1R,4R,5S,6R)-4,5,6-tris(benzyloxy)-3-(benzyloxymethyl)-1-(3-((5-(4-fluorophenyl)thiophen-2-yl)methyl)-4-methylphenyl)cyclohex-2-enol

Base Information

• Chemical Name: (1R,4R,5S,6R)-4,5,6-tris(benzyloxy)-3-(benzyloxymethyl)-1-(3-((5-(4-fluorophenyl)thiophen-2-yl)methyl)-4-methylphenyl)cyclohex-2-enol
• CAS No.: 1413373-77-9
• Molecular Formula: C₅₃H₄₉FO₅S
• Molecular Weight: 817.033
• Mol file: 1413373-77-9.mol

Synonyms:(1R,4R,5S,6R)-4,5,6-tris(benzyloxy)-3-(benzyloxymethyl)-1-(3-((5-(4-fluorophenyl)thiophen-2-yl)methyl)-4-methylphenyl)cyclohex-2-enol

Chemical Property of (1R,4R,5S,6R)-4,5,6-tris(benzyloxy)-3-(benzyloxymethyl)-1-(3-((5-(4-fluorophenyl)thiophen-2-yl)methyl)-4-methylphenyl)cyclohex-2-enol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,4R,5S,6R)-4,5,6-tris(benzyloxy)-3-(benzyloxymethyl)-1-(3-((5-(4-fluorophenyl)thiophen-2-yl)methyl)-4-methylphenyl)cyclohex-2-enol

There total 19 articles about (1R,4R,5S,6R)-4,5,6-tris(benzyloxy)-3-(benzyloxymethyl)-1-(3-((5-(4-fluorophenyl)thiophen-2-yl)methyl)-4-methylphenyl)cyclohex-2-enol 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: 75.6%

(2-(4-fluorophenyl)-5-[(5-iodo-2-methylphenyl)methyl]thiophene) (898566-17-1) + (4R,5S,6R)-4,5,6-tris(benzyloxy)-3-((benzyloxy)methyl)-2-cyclohexen-1-one (110391-10-1) → (1R,4R,5S,6R)-4,5,6-tris(benzyloxy)-3-(benzyloxymethyl)-1-(3-((5-(4-fluorophenyl)thiophen-2-yl)methyl)-4-methylphenyl)cyclohex-2-enol (1413373-77-9)

Guidance literature:

(2-(4-fluorophenyl)-5-[(5-iodo-2-methylphenyl)methyl]thiophene); With TurboGrignard; In tetrahydrofuran; at -10 ℃; for 1h; Inert atmosphere;

(4R,5S,6R)-4,5,6-tris(benzyloxy)-3-((benzyloxy)methyl)-2-cyclohexen-1-one; In tetrahydrofuran; at -10 - 0 ℃; for 4h; Inert atmosphere;

Reference yield:

3-[[5-(4-fluorophenyl)-2-thienyl]methyl]-4-methylphenyl bromide (1030825-20-7) + (4R,5S,6R)-4,5,6-tris(benzyloxy)-3-((benzyloxy)methyl)-2-cyclohexen-1-one (110391-10-1) → (1R,4R,5S,6R)-4,5,6-tris(benzyloxy)-3-(benzyloxymethyl)-1-(3-((5-(4-fluorophenyl)thiophen-2-yl)methyl)-4-methylphenyl)cyclohex-2-enol (1413373-77-9)

Guidance literature:

3-[[5-(4-fluorophenyl)-2-thienyl]methyl]-4-methylphenyl bromide; With n-butyllithium; In tetrahydrofuran; hexane; toluene; at -70 ℃; for 0.0833333h; Inert atmosphere;

(4R,5S,6R)-4,5,6-tris(benzyloxy)-3-((benzyloxy)methyl)-2-cyclohexen-1-one; In tetrahydrofuran; hexane; toluene; at -70 ℃; for 0.25h;

With water; In tetrahydrofuran; hexane; toluene;

Reference yield:

2,3,4,6-Tetra-O-benzyl-D-glucopyranose (4291-69-4,6386-24-9,6564-72-3,59531-24-7,69257-52-9,78184-89-1,78609-16-2,78609-17-3,78609-18-4,96553-53-6,104111-61-7,131347-08-5,4132-28-9) → (1R,4R,5S,6R)-4,5,6-tris(benzyloxy)-3-(benzyloxymethyl)-1-(3-((5-(4-fluorophenyl)thiophen-2-yl)methyl)-4-methylphenyl)cyclohex-2-enol (1413373-77-9)

Guidance literature:

Multi-step reaction with 5 steps

1.1: toluene; tetrahydrofuran / 3.67 h / 0 - 50 °C / Inert atmosphere

2.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1.25 h / -78 - -40 °C / Inert atmosphere

2.2: 2.25 h / -78 - 20 °C

3.1: L-proline / dimethyl sulfoxide / 8 h / 50 °C

4.1: pyridine; trichlorophosphate / 0 - 20 °C

5.1: n-butyllithium / toluene; hexane; tetrahydrofuran / 0.08 h / -70 °C / Inert atmosphere

5.2: 0.25 h / -70 °C

With pyridine; n-butyllithium; oxalyl dichloride; dimethyl sulfoxide; L-proline; trichlorophosphate; In tetrahydrofuran; hexane; dichloromethane; dimethyl sulfoxide; toluene;

upstream raw materials:

1-Bromo-4-fluorobenzene

2,3,4,6-Tetra-O-benzyl-D-glucopyranose

2-(4-fluorophenyl)thiophene

5-bromo-2-methylbenzoyl?chloride

Downstream raw materials:

2-(4-fluorophenyl)-5-(2-methyl-5-((3R,4R,5S,6S)-4,5,6-tris(benzyloxy)-3-(benzyloxymethyl)cyclohex-1-enyl)benzyl)thiophene