1-{(4R,5S)-5-[(E)-9-(2-Hexyl-5,5-dimethyl-[1,3]dioxan-2-yl)-non-2-enyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-2-trityloxy-ethanone

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Chemical Name:1-{(4R,5S)-5-[(E)-9-(2-Hexyl-5,5-dimethyl-[1,3]dioxan-2-yl)-non-2-enyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-2-trityloxy-ethanone
CAS No.:76183-01-2
Molecular Formula:C₄₇H₆₄O₆
Molecular Weight:725.022
Hs Code.:

Synonyms:1-{(4R,5S)-5-[(E)-9-(2-Hexyl-5,5-dimethyl-[1,3]dioxan-2-yl)-non-2-enyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-2-trityloxy-ethanone

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Chemical Property of 1-{(4R,5S)-5-[(E)-9-(2-Hexyl-5,5-dimethyl-[1,3]dioxan-2-yl)-non-2-enyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-2-trityloxy-ethanone

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Technology Process of 1-{(4R,5S)-5-[(E)-9-(2-Hexyl-5,5-dimethyl-[1,3]dioxan-2-yl)-non-2-enyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-2-trityloxy-ethanone

There total 17 articles about 1-{(4R,5S)-5-[(E)-9-(2-Hexyl-5,5-dimethyl-[1,3]dioxan-2-yl)-non-2-enyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-2-trityloxy-ethanone 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: 87.0%

: 78020-91-4
(S)-1-{(4S,5S)-5-[(E)-9-(2-Hexyl-5,5-dimethyl-[1,3]dioxan-2-yl)-non-2-enyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-2-trityloxy-ethanol

: 76183-01-2
1-{(4R,5S)-5-[(E)-9-(2-Hexyl-5,5-dimethyl-[1,3]dioxan-2-yl)-non-2-enyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-2-trityloxy-ethanone

Guidance literature:: With acetic anhydride; dimethyl sulfoxide; for 18h; Ambient temperature;
DOI:10.1139/v81-044

Reference yield:

: 76182-97-3
(Z)-1-hexylcyclooct-1-ene

: 76183-01-2
1-{(4R,5S)-5-[(E)-9-(2-Hexyl-5,5-dimethyl-[1,3]dioxan-2-yl)-non-2-enyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-2-trityloxy-ethanone

Guidance literature:: Multi-step reaction with 10 steps

1: 1.) ozone; 2.) sodium borohydride / 1.) -70 deg C, ethanol; 2.) ethanol, from -70 deg C to r.t., 2 h

2: 72 percent / hexamethyl phosphoric triamide, 8 percent NaHCO₃, bromine / CH₂Cl₂ / 5 °C

3: 97 percent / p-toluenesulfonic acid monohydrate / benzene / Heating; Dean Stark trap

4: 87 percent / triphenylphosphine, N-bromosuccinimide / dimethylformamide

5: 85 percent / trimethylorthophormate / acetonitrile / 14 h / 90 °C

6: 86 percent / 1.) 1.6 N n-BuLi / 1.) hexane, THF, 25 deg C, 10 min; 2.) THF, hexane, -70 deg C, 5 min

7: 95 percent / m-chloroperbenzoic acid / cyclohexane / 30 min, 5 deg C; 2.5 h, r.t.

8: 1.) 0.45 M lithium diphenylphosphide; 2.) methyl iodide / 1.) THF, 20 min, 25 deg C; 2.) 90 min, THF

9: 88 percent / tetra-n-butylammonium fluoride trihydrate / tetrahydrofuran / Heating

10: 87 percent / dimethyl sulfoxide, acetic anhydride / 18 h / Ambient temperature

With N,N,N,N,N,N-hexamethylphosphoric triamide; sodium tetrahydroborate; N-Bromosuccinimide; n-butyllithium; tetrabutyl ammonium fluoride; bromine; acetic anhydride; sodium hydrogencarbonate; ozone; dimethyl sulfoxide; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; lithium diphenylphosphide; methyl iodide; trimethyl orthoformate; toluene-4-sulfonic acid; In tetrahydrofuran; dichloromethane; cyclohexane; N,N-dimethyl-formamide; acetonitrile; benzene;
DOI:10.1139/v81-044

Reference yield:

: 39516-38-6
1,8-tetradecane diol

: 76183-01-2
1-{(4R,5S)-5-[(E)-9-(2-Hexyl-5,5-dimethyl-[1,3]dioxan-2-yl)-non-2-enyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-2-trityloxy-ethanone

Guidance literature:: Multi-step reaction with 9 steps

1: 72 percent / hexamethyl phosphoric triamide, 8 percent NaHCO₃, bromine / CH₂Cl₂ / 5 °C

2: 97 percent / p-toluenesulfonic acid monohydrate / benzene / Heating; Dean Stark trap

3: 87 percent / triphenylphosphine, N-bromosuccinimide / dimethylformamide

4: 85 percent / trimethylorthophormate / acetonitrile / 14 h / 90 °C

5: 86 percent / 1.) 1.6 N n-BuLi / 1.) hexane, THF, 25 deg C, 10 min; 2.) THF, hexane, -70 deg C, 5 min

6: 95 percent / m-chloroperbenzoic acid / cyclohexane / 30 min, 5 deg C; 2.5 h, r.t.

7: 1.) 0.45 M lithium diphenylphosphide; 2.) methyl iodide / 1.) THF, 20 min, 25 deg C; 2.) 90 min, THF

8: 88 percent / tetra-n-butylammonium fluoride trihydrate / tetrahydrofuran / Heating

9: 87 percent / dimethyl sulfoxide, acetic anhydride / 18 h / Ambient temperature

With N,N,N,N,N,N-hexamethylphosphoric triamide; N-Bromosuccinimide; n-butyllithium; tetrabutyl ammonium fluoride; bromine; acetic anhydride; sodium hydrogencarbonate; dimethyl sulfoxide; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; lithium diphenylphosphide; methyl iodide; trimethyl orthoformate; toluene-4-sulfonic acid; In tetrahydrofuran; dichloromethane; cyclohexane; N,N-dimethyl-formamide; acetonitrile; benzene;
DOI:10.1139/v81-044