rel-(12R,13S)-(2E,6E,10E)-2,6-dimethyl-10-<(benzyloxy)methyl>-12-(benyloxy)-13-isopropenyl-14-(phenylsulfonyl)-2,6,10-tetradecatrien-1-ol

Base Information

Chemical Name:rel-(12R,13S)-(2E,6E,10E)-2,6-dimethyl-10-<(benzyloxy)methyl>-12-(benyloxy)-13-isopropenyl-14-(phenylsulfonyl)-2,6,10-tetradecatrien-1-ol
CAS No.:100572-58-5
Molecular Formula:C₄₀H₅₀O₅S
Molecular Weight:642.9
Hs Code.:

Synonyms:rel-(12R,13S)-(2E,6E,10E)-2,6-dimethyl-10-<(benzyloxy)methyl>-12-(benyloxy)-13-isopropenyl-14-(phenylsulfonyl)-2,6,10-tetradecatrien-1-ol

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Chemical Property of rel-(12R,13S)-(2E,6E,10E)-2,6-dimethyl-10-<(benzyloxy)methyl>-12-(benyloxy)-13-isopropenyl-14-(phenylsulfonyl)-2,6,10-tetradecatrien-1-ol

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Technology Process of rel-(12R,13S)-(2E,6E,10E)-2,6-dimethyl-10-<(benzyloxy)methyl>-12-(benyloxy)-13-isopropenyl-14-(phenylsulfonyl)-2,6,10-tetradecatrien-1-ol

There total 14 articles about rel-(12R,13S)-(2E,6E,10E)-2,6-dimethyl-10-<(benzyloxy)methyl>-12-(benyloxy)-13-isopropenyl-14-(phenylsulfonyl)-2,6,10-tetradecatrien-1-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:

: 100572-57-4
((2E,6E,10E)-(12S,13R)-13-Benzenesulfonylmethyl-12-benzyloxy-10-benzyloxymethyl-2,6,14-trimethyl-pentadeca-2,6,10,14-tetraenyloxy)-tert-butyl-dimethyl-silane

: 100572-58-5
rel-(12R,13S)-(2E,6E,10E)-2,6-dimethyl-10-<(benzyloxy)methyl>-12-(benyloxy)-13-isopropenyl-14-(phenylsulfonyl)-2,6,10-tetradecatrien-1-ol

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; at 25 ℃; for 2h; Yield given;
DOI:10.1021/jo00356a021

Reference yield:

: 100229-51-4,100758-70-1
(S)-2-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-3-methyl-but-3-en-1-ol

: 100572-58-5
rel-(12R,13S)-(2E,6E,10E)-2,6-dimethyl-10-<(benzyloxy)methyl>-12-(benyloxy)-13-isopropenyl-14-(phenylsulfonyl)-2,6,10-tetradecatrien-1-ol

Guidance literature:: Multi-step reaction with 11 steps

1: 87 percent / n-Bu₃P / tetrahydrofuran / 18 h / 0 - 25 °C

2: 89 percent / Bio-Rad 50W-X₈ cation exchange resin / methanol / 18 h / 25 °C

3: 97 percent / 4-(N,N-dimethylamino)pyridine, Et₃N / CH₂Cl₂ / 18 h / 0 - 25 °C

4: 1.) tert-BuLi / 1.) THF, hexane, -78 deg C, 10 min, 2.) THF, hexane, HMPA, from -78 deg C to RT, 75 min

5: 83 percent / m-chloroperoxybenzoic acid / CH₂Cl₂ / 1 h / 0 °C

6: 83 percent / tetrabutylammonium fluoride / tetrahydrofuran / 3 h / 0 - 25 °C

7: 79 percent / pyridinium dichromate, 3-A molecular sieves / CH₂Cl₂ / 2 h

8: tetrahydrofuran; toluene / 32 h

9: 94 percent / i-Bu₂AlH / tetrahydrofuran; CH₂Cl₂ / 0.67 h / -78 °C

10: 1.) 1,10-phenanthroline, n-BuLi / 1.) THF, -78 deg C, 2.) THF, HMPA, from -78 deg C to RT,

11: tetra-n-butylammonium fluoride / tetrahydrofuran; hexamethylphosphoric acid triamide / 2 h / 25 °C

With dmap; dipyridinium dichromate; n-butyllithium; 1,10-Phenanthroline; tributylphosphine; 3 A molecular sieve; Bio-Rad 50W-X₈ cation exchange resin; tetrabutyl ammonium fluoride; tert.-butyl lithium; diisobutylaluminium hydride; triethylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; toluene;
DOI:10.1021/jo00356a021

Reference yield:

: 100572-42-7
rel-(5R,6S)-2,2-dimethyl-5-hydroxy-6-isopropenyl-1,3-dioxepane

: 100572-58-5
rel-(12R,13S)-(2E,6E,10E)-2,6-dimethyl-10-<(benzyloxy)methyl>-12-(benyloxy)-13-isopropenyl-14-(phenylsulfonyl)-2,6,10-tetradecatrien-1-ol

Guidance literature:: Multi-step reaction with 12 steps

1: 90 percent / p-TsOH / acetone / 25 °C

2: 87 percent / n-Bu₃P / tetrahydrofuran / 18 h / 0 - 25 °C

3: 89 percent / Bio-Rad 50W-X₈ cation exchange resin / methanol / 18 h / 25 °C

4: 97 percent / 4-(N,N-dimethylamino)pyridine, Et₃N / CH₂Cl₂ / 18 h / 0 - 25 °C

5: 1.) tert-BuLi / 1.) THF, hexane, -78 deg C, 10 min, 2.) THF, hexane, HMPA, from -78 deg C to RT, 75 min

6: 83 percent / m-chloroperoxybenzoic acid / CH₂Cl₂ / 1 h / 0 °C

7: 83 percent / tetrabutylammonium fluoride / tetrahydrofuran / 3 h / 0 - 25 °C

8: 79 percent / pyridinium dichromate, 3-A molecular sieves / CH₂Cl₂ / 2 h

9: tetrahydrofuran; toluene / 32 h

10: 94 percent / i-Bu₂AlH / tetrahydrofuran; CH₂Cl₂ / 0.67 h / -78 °C

11: 1.) 1,10-phenanthroline, n-BuLi / 1.) THF, -78 deg C, 2.) THF, HMPA, from -78 deg C to RT,

12: tetra-n-butylammonium fluoride / tetrahydrofuran; hexamethylphosphoric acid triamide / 2 h / 25 °C

With dmap; dipyridinium dichromate; n-butyllithium; 1,10-Phenanthroline; tributylphosphine; 3 A molecular sieve; Bio-Rad 50W-X₈ cation exchange resin; tetrabutyl ammonium fluoride; tert.-butyl lithium; diisobutylaluminium hydride; toluene-4-sulfonic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; acetone; toluene;
DOI:10.1021/jo00356a021