(1R,2R,3R,5S)-3-[(1Z)-2-hydroxy-1-tetradecylideneethyl]-7,7-dimethyl-4,6,8-trioxa-2-[(phenylmethoxy)methyl]bicyclo[3.3.0]octan-2-ol

Base Information

Chemical Name:(1R,2R,3R,5S)-3-[(1Z)-2-hydroxy-1-tetradecylideneethyl]-7,7-dimethyl-4,6,8-trioxa-2-[(phenylmethoxy)methyl]bicyclo[3.3.0]octan-2-ol
CAS No.:473290-36-7
Molecular Formula:C₃₁H₅₀O₆
Molecular Weight:518.734
Hs Code.:

Synonyms:(1R,2R,3R,5S)-3-[(1Z)-2-hydroxy-1-tetradecylideneethyl]-7,7-dimethyl-4,6,8-trioxa-2-[(phenylmethoxy)methyl]bicyclo[3.3.0]octan-2-ol

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Chemical Property of (1R,2R,3R,5S)-3-[(1Z)-2-hydroxy-1-tetradecylideneethyl]-7,7-dimethyl-4,6,8-trioxa-2-[(phenylmethoxy)methyl]bicyclo[3.3.0]octan-2-ol

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Technology Process of (1R,2R,3R,5S)-3-[(1Z)-2-hydroxy-1-tetradecylideneethyl]-7,7-dimethyl-4,6,8-trioxa-2-[(phenylmethoxy)methyl]bicyclo[3.3.0]octan-2-ol

There total 9 articles about (1R,2R,3R,5S)-3-[(1Z)-2-hydroxy-1-tetradecylideneethyl]-7,7-dimethyl-4,6,8-trioxa-2-[(phenylmethoxy)methyl]bicyclo[3.3.0]octan-2-ol 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: 55.0%

: 473290-33-4
(E)-2-[(3aR,5R,6S,6aR)-6-Benzyloxymethyl-6-(4-methoxy-benzyloxy)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl]-hexadec-2-en-1-ol

: 473290-36-7
(1R,2R,3R,5S)-3-[(1Z)-2-hydroxy-1-tetradecylideneethyl]-7,7-dimethyl-4,6,8-trioxa-2-[(phenylmethoxy)methyl]bicyclo[3.3.0]octan-2-ol

: 473290-34-5
(1R,2R,3R,5S)-3-[(1E)-2-hydroxy-1-tetradecylideneethyl]-7,7-dimethyl-4,6,8-trioxa-2-[(phenylmethoxy)methyl]bicyclo[3.3.0]octan-2-ol

Guidance literature:: With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; water; at 20 ℃;
DOI:10.1016/S0040-4020(02)00477-5

Reference yield:

: 53270-27-2
3,3'-anhydro-3-C-hydroxymethyl-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose

: 473290-36-7
(1R,2R,3R,5S)-3-[(1Z)-2-hydroxy-1-tetradecylideneethyl]-7,7-dimethyl-4,6,8-trioxa-2-[(phenylmethoxy)methyl]bicyclo[3.3.0]octan-2-ol

Guidance literature:: Multi-step reaction with 8 steps

1: 98 percent / NaH / tetrahydrofuran / 36 h / Heating

2: 96 percent / NaH; Bu₄NI / tetrahydrofuran / 3 h / Heating

3: 95 percent / aq. HCl / ethanol / 16 h / 20 °C

4: 99 percent / imidazole / CH₂Cl₂; dimethylformamide / 19 h / 20 °C

5: 80 percent / 4 Angstroem molecular sieves; pyridinium chlorochromate / CH₂Cl₂ / 0.67 h / 20 °C

6: 34 percent / n-BuLi / tetrahydrofuran; hexane; toluene / 17.5 h / -30 - 20 °C

7: tetra-n-butylammonium fluoride / tetrahydrofuran / 5 h / 20 °C

8: 55 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH₂Cl₂; H₂O / 20 °C

With 1H-imidazole; hydrogenchloride; n-butyllithium; 4 A molecular sieve; tetrabutyl ammonium fluoride; tetra-(n-butyl)ammonium iodide; sodium hydride; pyridinium chlorochromate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; ethanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; toluene; 6: Wittig reaction;
DOI:10.1016/S0040-4020(02)00477-5

Reference yield:

: 25791-20-2
(n-tetradecyl)triphenylphosphonium bromide

: 473290-36-7
(1R,2R,3R,5S)-3-[(1Z)-2-hydroxy-1-tetradecylideneethyl]-7,7-dimethyl-4,6,8-trioxa-2-[(phenylmethoxy)methyl]bicyclo[3.3.0]octan-2-ol

Guidance literature:: Multi-step reaction with 3 steps

1: 34 percent / n-BuLi / tetrahydrofuran; hexane; toluene / 17.5 h / -30 - 20 °C

2: tetra-n-butylammonium fluoride / tetrahydrofuran / 5 h / 20 °C

3: 55 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH₂Cl₂; H₂O / 20 °C

With n-butyllithium; tetrabutyl ammonium fluoride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; hexane; dichloromethane; water; toluene; 1: Wittig reaction;
DOI:10.1016/S0040-4020(02)00477-5