phosphoric acid 4-[2-(2-benzyloxy-propyl)-[1,3]dioxolan-2-ylmethyl]-5-oxo-1,4,4a,5,8,8a-hexahydro-naphthalen-2-yl ester diethyl ester

Base Information

Chemical Name:phosphoric acid 4-[2-(2-benzyloxy-propyl)-[1,3]dioxolan-2-ylmethyl]-5-oxo-1,4,4a,5,8,8a-hexahydro-naphthalen-2-yl ester diethyl ester
CAS No.:500770-24-1
Molecular Formula:C₂₈H₃₉O₈P
Molecular Weight:534.587
Hs Code.:

Synonyms:phosphoric acid 4-[2-(2-benzyloxy-propyl)-[1,3]dioxolan-2-ylmethyl]-5-oxo-1,4,4a,5,8,8a-hexahydro-naphthalen-2-yl ester diethyl ester

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Chemical Property of phosphoric acid 4-[2-(2-benzyloxy-propyl)-[1,3]dioxolan-2-ylmethyl]-5-oxo-1,4,4a,5,8,8a-hexahydro-naphthalen-2-yl ester diethyl ester

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Technology Process of phosphoric acid 4-[2-(2-benzyloxy-propyl)-[1,3]dioxolan-2-ylmethyl]-5-oxo-1,4,4a,5,8,8a-hexahydro-naphthalen-2-yl ester diethyl ester

There total 9 articles about phosphoric acid 4-[2-(2-benzyloxy-propyl)-[1,3]dioxolan-2-ylmethyl]-5-oxo-1,4,4a,5,8,8a-hexahydro-naphthalen-2-yl ester diethyl ester 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:

: 930-68-7
cyclohexenone

: 500770-24-1
phosphoric acid 4-[2-(2-benzyloxy-propyl)-[1,3]dioxolan-2-ylmethyl]-5-oxo-1,4,4a,5,8,8a-hexahydro-naphthalen-2-yl ester diethyl ester

Guidance literature:: Multi-step reaction with 9 steps

1.1: 64 percent / BF₃*Et₂O / toluene / 12 h / 20 °C

2.1: LiN(TMS)2 / tetrahydrofuran / 0.08 h / 20 °C

2.2: 68 percent / 30 percent H₂O₂; aq. NaHCO₃ / CH₂Cl₂ / 36 h / 20 °C

3.1: 81 percent / NaBH₄; CeCl₃*7H₂O; NaOEt / ethanol / 12 h / 0 - 40 °C

4.1: 86 percent / (COCl)2; Et₃N / dimethylsulfoxide; CH₂Cl₂ / 1 h / -78 - 20 °C

5.1: 81 percent / tetrahydrofuran / 1 h / -10 °C

6.1: 84 percent / o-iodoxybenzoic acid / toluene; dimethylsulfoxide / 3 h / 20 °C

7.1: 85 percent / diisopinocampheylchloroborane; Et₃N / CH₂Cl₂ / 4 h / -78 - 20 °C

8.1: 75 percent / TMSOTf / CH₂Cl₂; cyclohexane / 2 h / 20 °C

9.1: 75 percent / TMSOTf / CH₂Cl₂ / 1 h / -78 - 0 °C

With sodium tetrahydroborate; cerium(III) chloride; oxalyl dichloride; trimethylsilyl trifluoromethanesulfonate; diisopinocamphenylchloroborane; boron trifluoride diethyl etherate; sodium ethanolate; triethylamine; lithium hexamethyldisilazane; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; ethanol; dichloromethane; cyclohexane; dimethyl sulfoxide; toluene; 5.1: Grignard reaction;
DOI:10.7164/antibiotics.55.1076

Reference yield:

: 500770-29-6
phosphoric acid diethyl ester 5-oxo-4-(2-oxo-ethyl)-1,4,4a,5,8,8a-hexahydro-naphthalen-2-yl ester

: 500770-24-1
phosphoric acid 4-[2-(2-benzyloxy-propyl)-[1,3]dioxolan-2-ylmethyl]-5-oxo-1,4,4a,5,8,8a-hexahydro-naphthalen-2-yl ester diethyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 81 percent / tetrahydrofuran / 1 h / -10 °C

2: 84 percent / o-iodoxybenzoic acid / toluene; dimethylsulfoxide / 3 h / 20 °C

3: 85 percent / diisopinocampheylchloroborane; Et₃N / CH₂Cl₂ / 4 h / -78 - 20 °C

4: 75 percent / TMSOTf / CH₂Cl₂; cyclohexane / 2 h / 20 °C

5: 75 percent / TMSOTf / CH₂Cl₂ / 1 h / -78 - 0 °C

With trimethylsilyl trifluoromethanesulfonate; diisopinocamphenylchloroborane; triethylamine; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; dichloromethane; cyclohexane; dimethyl sulfoxide; toluene; 1: Grignard reaction;
DOI:10.7164/antibiotics.55.1076

Reference yield:

: 500770-38-7
phosphoric acid diethyl ester 4-(2-hydroxy-ethyl)-5-oxo-1,4,4a,5,8,8a-hexahydro-naphthalen-2-yl ester

: 500770-24-1
phosphoric acid 4-[2-(2-benzyloxy-propyl)-[1,3]dioxolan-2-ylmethyl]-5-oxo-1,4,4a,5,8,8a-hexahydro-naphthalen-2-yl ester diethyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 86 percent / (COCl)2; Et₃N / dimethylsulfoxide; CH₂Cl₂ / 1 h / -78 - 20 °C

2: 81 percent / tetrahydrofuran / 1 h / -10 °C

3: 84 percent / o-iodoxybenzoic acid / toluene; dimethylsulfoxide / 3 h / 20 °C

4: 85 percent / diisopinocampheylchloroborane; Et₃N / CH₂Cl₂ / 4 h / -78 - 20 °C

5: 75 percent / TMSOTf / CH₂Cl₂; cyclohexane / 2 h / 20 °C

6: 75 percent / TMSOTf / CH₂Cl₂ / 1 h / -78 - 0 °C

With oxalyl dichloride; trimethylsilyl trifluoromethanesulfonate; diisopinocamphenylchloroborane; triethylamine; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; dichloromethane; cyclohexane; dimethyl sulfoxide; toluene; 2: Grignard reaction;
DOI:10.7164/antibiotics.55.1076