(1S,2R,6S,8R)-8-Benzyloxymethyl-6,9,9-trimethyl-2-trityloxymethyl-12-oxa-tricyclo[6.3.1.0^1,6]dodecan-11-one

Base Information

• Chemical Name: (1S,2R,6S,8R)-8-Benzyloxymethyl-6,9,9-trimethyl-2-trityloxymethyl-12-oxa-tricyclo[6.3.1.0^1,6]dodecan-11-one
• CAS No.: 184869-00-9
• Molecular Formula: C₄₂H₄₆O₄
• Molecular Weight: 614.825

Synonyms:(1S,2R,6S,8R)-8-Benzyloxymethyl-6,9,9-trimethyl-2-trityloxymethyl-12-oxa-tricyclo[6.3.1.0^1,6]dodecan-11-one

Chemical Property of (1S,2R,6S,8R)-8-Benzyloxymethyl-6,9,9-trimethyl-2-trityloxymethyl-12-oxa-tricyclo[6.3.1.0^1,6]dodecan-11-one

Chemical Property:

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Technology Process of (1S,2R,6S,8R)-8-Benzyloxymethyl-6,9,9-trimethyl-2-trityloxymethyl-12-oxa-tricyclo[6.3.1.0^1,6]dodecan-11-one

There total 11 articles about (1S,2R,6S,8R)-8-Benzyloxymethyl-6,9,9-trimethyl-2-trityloxymethyl-12-oxa-tricyclo[6.3.1.0^1,6]dodecan-11-one 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%

methylmagnesium bromide (75-16-1) + (1S,2R,6S,8R)-8-Benzyloxymethyl-6,9-dimethyl-2-trityloxymethyl-12-oxa-tricyclo[6.3.1.01,6]dodec-9-en-11-one (184868-99-3) → (1S,2R,6S,8R)-8-Benzyloxymethyl-6,9,9-trimethyl-2-trityloxymethyl-12-oxa-tricyclo[6.3.1.01,6]dodecan-11-one (184869-00-9)

Guidance literature:

With copper(I) bromide dimethylsulfide complex; In diethyl ether; at 25 ℃; for 4h;

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

Reference yield:

(3-methylfuran-2-yl)methanol (20416-16-4) → (1S,2R,6S,8R)-8-Benzyloxymethyl-6,9,9-trimethyl-2-trityloxymethyl-12-oxa-tricyclo[6.3.1.01,6]dodecan-11-one (184869-00-9)

Guidance literature:

Multi-step reaction with 10 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

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

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

Reference yield:

methyl 3-methylfuran-2-carboxylate (6141-57-7) → (1S,2R,6S,8R)-8-Benzyloxymethyl-6,9,9-trimethyl-2-trityloxymethyl-12-oxa-tricyclo[6.3.1.01,6]dodecan-11-one (184869-00-9)

Guidance literature:

Multi-step reaction with 11 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

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; rose bengal; sodium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; lithium hexamethyldisilazane; In tetrahydrofuran; diethyl ether; dichloromethane; toluene;

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

upstream raw materials:

methylmagnesium bromide

(1S,2R,6S,8R)-8-Benzyloxymethyl-6,9-dimethyl-2-trityloxymethyl-12-oxa-tricyclo[6.3.1.0^1,6]dodec-9-en-11-one

(3-methylfuran-2-yl)methanol

methyl 3-methylfuran-2-carboxylate

Downstream raw materials:

(1S,2R,6S,8R)-8-Benzyloxymethyl-6,9,9-trimethyl-10-methylene-2-trityloxymethyl-12-oxa-tricyclo[6.3.1.0^1,6]dodecan-11-one

(1S,2R,6S,8R)-8-Benzyloxymethyl-2-hydroxymethyl-6,9,9-trimethyl-10-methylene-12-oxa-tricyclo[6.3.1.0^1,6]dodecan-11-one

(1S,2R,6S,8R,10R)-8-Benzyloxymethyl-2-hydroxymethyl-6,9,9-trimethyl-10-(2-oxo-butyl)-12-oxa-tricyclo[6.3.1.0^1,6]dodecan-11-one

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

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