(1R,2S,3R)-5-[2-Benzyloxy-eth-(Z)-ylidene]-3-(4-methoxy-benzyloxy)-2-methyl-cyclohexanol

Base Information

Chemical Name:(1R,2S,3R)-5-[2-Benzyloxy-eth-(Z)-ylidene]-3-(4-methoxy-benzyloxy)-2-methyl-cyclohexanol
CAS No.:259676-59-0
Molecular Formula:C₂₄H₃₀O₄
Molecular Weight:382.5
Hs Code.:

Synonyms:

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (1R,2S,3R)-5-[2-Benzyloxy-eth-(Z)-ylidene]-3-(4-methoxy-benzyloxy)-2-methyl-cyclohexanol

Chemical Property:

Purity/Quality:

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Technology Process of (1R,2S,3R)-5-[2-Benzyloxy-eth-(Z)-ylidene]-3-(4-methoxy-benzyloxy)-2-methyl-cyclohexanol

There total 9 articles about (1R,2S,3R)-5-[2-Benzyloxy-eth-(Z)-ylidene]-3-(4-methoxy-benzyloxy)-2-methyl-cyclohexanol 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:

: 2186-92-7
p-Anisaldehyde dimethyl acetal

: 259676-59-0
(1R,2S,3R)-5-[2-Benzyloxy-eth-(Z)-ylidene]-3-(4-methoxy-benzyloxy)-2-methyl-cyclohexanol

Guidance literature:: Multi-step reaction with 6 steps

1: PPTS / CH₂Cl₂ / 20 °C

2: TBAF / tetrahydrofuran

3: NaH; TBAI

4: DIBAL-H / CH₂Cl₂ / 0 - 20 °C

5: PCC; molecular sieves 3 Angstroem / CH₂Cl₂ / 20 °C

6: (R)-6-Br-BINOL; Cl₂Ti(O-i-Pr)2; molecular sieves 4 Angstroem / 12 h / 20 °C

With titanium(IV) dichlorodiisopropylate; 3 A molecular sieve; 4 A molecular sieve; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; pyridinium chlorochromate; (R)-6-bromo-2,2'-dihydroxy-1,1'-binaphthalene; In tetrahydrofuran; dichloromethane; 1: Etherification / 2: Desilylation / 3: Etherification / 4: Reduction / 5: Oxidation / 6: Cyclization;
DOI:10.1055/s-1999-2989

Reference yield:

: (E)-5-Methylene-7-triethylsilanyloxy-hept-2-en-1-ol

: 259676-59-0
(1R,2S,3R)-5-[2-Benzyloxy-eth-(Z)-ylidene]-3-(4-methoxy-benzyloxy)-2-methyl-cyclohexanol

Guidance literature:: Multi-step reaction with 8 steps

1: 78 percent / (-)-S,S-diethyl tartrate; titanium tetraisopropoxide; tert-BuOOH / CH₂Cl₂ / -30 °C

2: CuBr*Me₂S / tetrahydrofuran; diethyl ether / -40 - 20 °C

3: PPTS / CH₂Cl₂ / 20 °C

4: TBAF / tetrahydrofuran

5: NaH; TBAI

6: DIBAL-H / CH₂Cl₂ / 0 - 20 °C

7: PCC; molecular sieves 3 Angstroem / CH₂Cl₂ / 20 °C

8: (R)-6-Br-BINOL; Cl₂Ti(O-i-Pr)2; molecular sieves 4 Angstroem / 12 h / 20 °C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; titanium(IV) dichlorodiisopropylate; copper(I) bromide dimethylsulfide complex; diethyl (2S,3S)-tartrate; 3 A molecular sieve; 4 A molecular sieve; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; pyridinium chlorochromate; (R)-6-bromo-2,2'-dihydroxy-1,1'-binaphthalene; In tetrahydrofuran; diethyl ether; dichloromethane; 1: Epoxidation / 2: Methylation / 3: Etherification / 4: Desilylation / 5: Etherification / 6: Reduction / 7: Oxidation / 8: Cyclization;
DOI:10.1055/s-1999-2989

Reference yield:

: 3-[(4R,5S)-2-(4-Methoxy-phenyl)-5-methyl-[1,3]dioxan-4-ylmethyl]-but-3-en-1-ol

: 259676-59-0
(1R,2S,3R)-5-[2-Benzyloxy-eth-(Z)-ylidene]-3-(4-methoxy-benzyloxy)-2-methyl-cyclohexanol

Guidance literature:: Multi-step reaction with 4 steps

1: NaH; TBAI

2: DIBAL-H / CH₂Cl₂ / 0 - 20 °C

3: PCC; molecular sieves 3 Angstroem / CH₂Cl₂ / 20 °C

4: (R)-6-Br-BINOL; Cl₂Ti(O-i-Pr)2; molecular sieves 4 Angstroem / 12 h / 20 °C

With titanium(IV) dichlorodiisopropylate; 3 A molecular sieve; 4 A molecular sieve; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; pyridinium chlorochromate; (R)-6-bromo-2,2'-dihydroxy-1,1'-binaphthalene; In dichloromethane; 1: Etherification / 2: Reduction / 3: Oxidation / 4: Cyclization;
DOI:10.1055/s-1999-2989