2-(3-benzyloxy-propyl)-6-bromo-4-(1-bromo-propyl)-3,8-dioxa-bicyclo[5.1.1]nonane

Base Information

Chemical Name:2-(3-benzyloxy-propyl)-6-bromo-4-(1-bromo-propyl)-3,8-dioxa-bicyclo[5.1.1]nonane
CAS No.:934977-29-4
Molecular Formula:C₂₀H₂₈Br₂O₃
Molecular Weight:476.249
Hs Code.:

Synonyms:2-(3-benzyloxy-propyl)-6-bromo-4-(1-bromo-propyl)-3,8-dioxa-bicyclo[5.1.1]nonane

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Chemical Property of 2-(3-benzyloxy-propyl)-6-bromo-4-(1-bromo-propyl)-3,8-dioxa-bicyclo[5.1.1]nonane

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Technology Process of 2-(3-benzyloxy-propyl)-6-bromo-4-(1-bromo-propyl)-3,8-dioxa-bicyclo[5.1.1]nonane

There total 19 articles about 2-(3-benzyloxy-propyl)-6-bromo-4-(1-bromo-propyl)-3,8-dioxa-bicyclo[5.1.1]nonane 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: 82.0%

: 934977-28-3
1-[2-(3-benzyloxy-propyl)-6-bromo-3,8-dioxa-bicyclo[5.1.1]non-4-yl]-propan-1-ol

: 934977-29-4
2-(3-benzyloxy-propyl)-6-bromo-4-(1-bromo-propyl)-3,8-dioxa-bicyclo[5.1.1]nonane

Guidance literature:: With 1-methylcyclohex-1-ene; carbon tetrabromide; TOP; In toluene; at 20 - 80 ℃; for 4h;
DOI:10.1021/ja068346i

Reference yield:

: 934977-35-2
1-benzyloxy-5-(4-methoxy-benzyloxy)-9-(tetrahydro-pyran-2-yloxy)-non-7-en-4-ol

: 934977-29-4
2-(3-benzyloxy-propyl)-6-bromo-4-(1-bromo-propyl)-3,8-dioxa-bicyclo[5.1.1]nonane

Guidance literature:: Multi-step reaction with 17 steps

1.1: NaH / tetrahydrofuran / 0.17 h / 0 °C

1.2: 100 percent / tetrahydrofuran / 4 h / 20 °C

2.1: 97 percent / ethanol / PTSA / 3 h / 20 °C

3.1: 92 percent / Ph₃P; CCl₄ / 2 h / Heating

4.1: 89 percent / KHMDS / toluene / 0.5 h / 20 °C

5.1: 99 percent / DDQ / CH₂Cl₂; H₂O / 2 h / 20 °C / pH 7.0 / buffered reaction

6.1: CCl₄; 1-methylcyclohexene; tri-n-octylphosphine / toluene / 12 h / 70 °C

7.1: 430.0 mg / NMO / OsO₄ / acetone; H₂O / 4 h / 0 °C

8.1: dibutyltin oxide / toluene / 2 h / Heating

8.2: 80 percent / TBAI / toluene / 1 h / Heating

9.1: 90 percent / NaH / dimethylformamide / 12 h / 20 °C

10.1: 94 percent / tetrahydrofuran / 1 h / 20 °C

11.1: 95 percent / KOH / tetrahydrofuran; methanol; H₂O / 12 h / 20 °C

12.1: 96 percent / lithium tri-sec-butylborohydride / tetrahydrofuran / 0.5 h / -78 °C

13.1: 90 percent / diisopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 12 h / 20 - 40 °C

14.1: 95 percent / DDQ / CH₂Cl₂; H₂O / 2 h / 20 °C / pH 7.0 / buffered reaction

15.1: 81 percent / CBr₄; tri-n-octylphosphine; pyridine / toluene / 4 h / 80 °C

16.1: 90 percent / LiAlH₄ / tetrahydrofuran / 1 h / 20 °C

17.1: 82 percent / CBr₄; tri-n-octylphosphine; 1-methylcyclohexene / toluene / 4 h / 20 - 80 °C

With pyridine; tetrachloromethane; potassium hydroxide; lithium aluminium tetrahydride; N-methyl-2-indolinone; 1-methylcyclohex-1-ene; ethanol; carbon tetrabromide; TOP; di-isopropyl azodicarboxylate; potassium hexamethylsilazane; L-Selectride; sodium hydride; di(n-butyl)tin oxide; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; osmium(VIII) oxide; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; 13.1: Mitsunobu reaction;
DOI:10.1021/ja068346i

Reference yield:

: 934977-36-3
2-[1-(3-benzyloxy-propyl)-2-(4-methoxy-benzyloxy)-6-(tetrahydro-pyran-2-yloxy)-hex-4-enyloxy]-N,N-dimethyl-acetamide

: 934977-29-4
2-(3-benzyloxy-propyl)-6-bromo-4-(1-bromo-propyl)-3,8-dioxa-bicyclo[5.1.1]nonane

Guidance literature:: Multi-step reaction with 16 steps

1.1: 97 percent / ethanol / PTSA / 3 h / 20 °C

2.1: 92 percent / Ph₃P; CCl₄ / 2 h / Heating

3.1: 89 percent / KHMDS / toluene / 0.5 h / 20 °C

4.1: 99 percent / DDQ / CH₂Cl₂; H₂O / 2 h / 20 °C / pH 7.0 / buffered reaction

5.1: CCl₄; 1-methylcyclohexene; tri-n-octylphosphine / toluene / 12 h / 70 °C

6.1: 430.0 mg / NMO / OsO₄ / acetone; H₂O / 4 h / 0 °C

7.1: dibutyltin oxide / toluene / 2 h / Heating

7.2: 80 percent / TBAI / toluene / 1 h / Heating

8.1: 90 percent / NaH / dimethylformamide / 12 h / 20 °C

9.1: 94 percent / tetrahydrofuran / 1 h / 20 °C

10.1: 95 percent / KOH / tetrahydrofuran; methanol; H₂O / 12 h / 20 °C

11.1: 96 percent / lithium tri-sec-butylborohydride / tetrahydrofuran / 0.5 h / -78 °C

12.1: 90 percent / diisopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 12 h / 20 - 40 °C

13.1: 95 percent / DDQ / CH₂Cl₂; H₂O / 2 h / 20 °C / pH 7.0 / buffered reaction

14.1: 81 percent / CBr₄; tri-n-octylphosphine; pyridine / toluene / 4 h / 80 °C

15.1: 90 percent / LiAlH₄ / tetrahydrofuran / 1 h / 20 °C

16.1: 82 percent / CBr₄; tri-n-octylphosphine; 1-methylcyclohexene / toluene / 4 h / 20 - 80 °C

With pyridine; tetrachloromethane; potassium hydroxide; lithium aluminium tetrahydride; N-methyl-2-indolinone; 1-methylcyclohex-1-ene; ethanol; carbon tetrabromide; TOP; di-isopropyl azodicarboxylate; potassium hexamethylsilazane; L-Selectride; sodium hydride; di(n-butyl)tin oxide; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; osmium(VIII) oxide; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; 12.1: Mitsunobu reaction;
DOI:10.1021/ja068346i