(-)-4α-hydroxymethyl-8β,11,11-trimethyl-10β-benzyloxymethyl-3α,10α-oxido-1,2-(2-ethoxypyranenyl)-bicyclo[5.4.0^3,8]undecane

Base Information

• Chemical Name: (-)-4α-hydroxymethyl-8β,11,11-trimethyl-10β-benzyloxymethyl-3α,10α-oxido-1,2-(2-ethoxypyranenyl)-bicyclo[5.4.0^3,8]undecane
• CAS No.: 184869-12-3
• Molecular Formula: C₂₈H₄₀O₅
• Molecular Weight: 456.623

Synonyms:(-)-4α-hydroxymethyl-8β,11,11-trimethyl-10β-benzyloxymethyl-3α,10α-oxido-1,2-(2-ethoxypyranenyl)-bicyclo[5.4.0^3,8]undecane

Chemical Property of (-)-4α-hydroxymethyl-8β,11,11-trimethyl-10β-benzyloxymethyl-3α,10α-oxido-1,2-(2-ethoxypyranenyl)-bicyclo[5.4.0^3,8]undecane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (-)-4α-hydroxymethyl-8β,11,11-trimethyl-10β-benzyloxymethyl-3α,10α-oxido-1,2-(2-ethoxypyranenyl)-bicyclo[5.4.0^3,8]undecane

There total 13 articles about (-)-4α-hydroxymethyl-8β,11,11-trimethyl-10β-benzyloxymethyl-3α,10α-oxido-1,2-(2-ethoxypyranenyl)-bicyclo[5.4.0^3,8]undecane 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:

(3-methylfuran-2-yl)methanol (20416-16-4) → (-)-4α-hydroxymethyl-8β,11,11-trimethyl-10β-benzyloxymethyl-3α,10α-oxido-1,2-(2-ethoxypyranenyl)-bicyclo[5.4.03,8]undecane (184869-12-3)

Guidance literature:

Multi-step reaction with 13 steps

1: 1.) n-BuLi / 1.) THF, 0 deg C, 2.5 h, 2.) THF, -40 deg C, 1.25 h

2: 1.) NaH, 2.) n-Bu₄NI / 1.) DMF, 25 deg C, 1 h, 2.) DMF, 100 deg C, 18 h

3: 63 percent / aq. NaOH / tetrahydrofuran / 18 h / Heating

4: oxalyl chloride / CH₂Cl₂ / 19 h / 0 - 25 °C

5: 1.) LiN(TMS)2, 3.) LiBH₄

6: 80 percent / DMAP, Et₃N / CH₂Cl₂ / 12 h / 25 °C

7: 1.) O₂, rose bengal, 2.) Me₂S / 1.) CH₂Cl₂, CH₃OH, irradiation, -55 deg C, 12 h, 2.) CH₂Cl₂, CH₃OH, from -55 deg C to 25 deg C

8: 37 g / DMAP, Et₃N / CH₂Cl₂ / 10 h / 25 °C

9: DBU / toluene / 10 h

10: 95 percent / CuBr*SMe₂ / diethyl ether / 4 h / 25 °C

11: 1.) KN(TMS)2 / 1.) THF, 25 deg C, 15 min, 2.) THF, 25 deg C, 30 min

12: 89 percent / p-TsOH / CH₂Cl₂; methanol / 5 h / Ambient temperature

13: 84 percent / Eu(FOD)3 / 48 h / Heating

With dmap; sodium hydroxide; lithium borohydride; n-butyllithium; oxalyl dichloride; copper(I) bromide dimethylsulfide complex; dimethylsulfide; oxygen; tetra-(n-butyl)ammonium iodide; potassium hexamethylsilazane; rose bengal; sodium hydride; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; lithium hexamethyldisilazane; Eu(fod)3; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; toluene;

DOI:10.1016/0040-4020(96)00865-4

Reference yield:

methyl 3-methylfuran-2-carboxylate (6141-57-7) → (-)-4α-hydroxymethyl-8β,11,11-trimethyl-10β-benzyloxymethyl-3α,10α-oxido-1,2-(2-ethoxypyranenyl)-bicyclo[5.4.03,8]undecane (184869-12-3)

Guidance literature:

Multi-step reaction with 14 steps

1: 93 percent / LiAlH₄ / tetrahydrofuran / 1 h / 0 °C

2: 1.) n-BuLi / 1.) THF, 0 deg C, 2.5 h, 2.) THF, -40 deg C, 1.25 h

3: 1.) NaH, 2.) n-Bu₄NI / 1.) DMF, 25 deg C, 1 h, 2.) DMF, 100 deg C, 18 h

4: 63 percent / aq. NaOH / tetrahydrofuran / 18 h / Heating

5: oxalyl chloride / CH₂Cl₂ / 19 h / 0 - 25 °C

6: 1.) LiN(TMS)2, 3.) LiBH₄

7: 80 percent / DMAP, Et₃N / CH₂Cl₂ / 12 h / 25 °C

8: 1.) O₂, rose bengal, 2.) Me₂S / 1.) CH₂Cl₂, CH₃OH, irradiation, -55 deg C, 12 h, 2.) CH₂Cl₂, CH₃OH, from -55 deg C to 25 deg C

9: 37 g / DMAP, Et₃N / CH₂Cl₂ / 10 h / 25 °C

10: DBU / toluene / 10 h

11: 95 percent / CuBr*SMe₂ / diethyl ether / 4 h / 25 °C

12: 1.) KN(TMS)2 / 1.) THF, 25 deg C, 15 min, 2.) THF, 25 deg C, 30 min

13: 89 percent / p-TsOH / CH₂Cl₂; methanol / 5 h / Ambient temperature

14: 84 percent / Eu(FOD)3 / 48 h / Heating

With dmap; sodium hydroxide; lithium aluminium tetrahydride; lithium borohydride; n-butyllithium; oxalyl dichloride; copper(I) bromide dimethylsulfide complex; dimethylsulfide; oxygen; tetra-(n-butyl)ammonium iodide; potassium hexamethylsilazane; rose bengal; sodium hydride; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; lithium hexamethyldisilazane; Eu(fod)3; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; toluene;

DOI:10.1016/0040-4020(96)00865-4

Reference yield:

5-Hydroxymethyl-4-methyl-furan-2-carboxylic acid (130446-62-7) → (-)-4α-hydroxymethyl-8β,11,11-trimethyl-10β-benzyloxymethyl-3α,10α-oxido-1,2-(2-ethoxypyranenyl)-bicyclo[5.4.03,8]undecane (184869-12-3)

Guidance literature:

Multi-step reaction with 12 steps

1: 1.) NaH, 2.) n-Bu₄NI / 1.) DMF, 25 deg C, 1 h, 2.) DMF, 100 deg C, 18 h

2: 63 percent / aq. NaOH / tetrahydrofuran / 18 h / Heating

3: oxalyl chloride / CH₂Cl₂ / 19 h / 0 - 25 °C

4: 1.) LiN(TMS)2, 3.) LiBH₄

5: 80 percent / DMAP, Et₃N / CH₂Cl₂ / 12 h / 25 °C

6: 1.) O₂, rose bengal, 2.) Me₂S / 1.) CH₂Cl₂, CH₃OH, irradiation, -55 deg C, 12 h, 2.) CH₂Cl₂, CH₃OH, from -55 deg C to 25 deg C

7: 37 g / DMAP, Et₃N / CH₂Cl₂ / 10 h / 25 °C

8: DBU / toluene / 10 h

9: 95 percent / CuBr*SMe₂ / diethyl ether / 4 h / 25 °C

10: 1.) KN(TMS)2 / 1.) THF, 25 deg C, 15 min, 2.) THF, 25 deg C, 30 min

11: 89 percent / p-TsOH / CH₂Cl₂; methanol / 5 h / Ambient temperature

12: 84 percent / Eu(FOD)3 / 48 h / Heating

With dmap; sodium hydroxide; lithium borohydride; oxalyl dichloride; copper(I) bromide dimethylsulfide complex; dimethylsulfide; oxygen; tetra-(n-butyl)ammonium iodide; potassium hexamethylsilazane; rose bengal; sodium hydride; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; lithium hexamethyldisilazane; Eu(fod)3; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; toluene;

DOI:10.1016/0040-4020(96)00865-4

upstream raw materials:

(3-methylfuran-2-yl)methanol

methyl 3-methylfuran-2-carboxylate

5-Hydroxymethyl-4-methyl-furan-2-carboxylic acid

5-Benzyloxymethyl-4-methyl-furan-2-carboxylic acid

Downstream raw materials:

(-)-4α-formyl-8β,11,11-trimethyl-10β-benzyloxymethyl-3α,10α-oxido-1,2-(2-ethoxypyranenyl)-bicyclo[5.4.0^3,8]undecane

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