(1R)-1-(hydroxymethyl)-3-(phenylselenomethyl)-2-oxaspiro[4.5]decan-8-one

Base Information

Chemical Name:(1R)-1-(hydroxymethyl)-3-(phenylselenomethyl)-2-oxaspiro[4.5]decan-8-one
CAS No.:915019-37-3
Molecular Formula:C₁₇H₂₂O₃Se
Molecular Weight:353.32
Hs Code.:

Synonyms:(1R)-1-(hydroxymethyl)-3-(phenylselenomethyl)-2-oxaspiro[4.5]decan-8-one

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Chemical Property of (1R)-1-(hydroxymethyl)-3-(phenylselenomethyl)-2-oxaspiro[4.5]decan-8-one

Chemical Property:

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Technology Process of (1R)-1-(hydroxymethyl)-3-(phenylselenomethyl)-2-oxaspiro[4.5]decan-8-one

There total 6 articles about (1R)-1-(hydroxymethyl)-3-(phenylselenomethyl)-2-oxaspiro[4.5]decan-8-one 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%

: 915019-36-2
(R)-4-(1,2-dihydroxyethyl)-4-(prop-2-enyl)cyclohexan-1-one 1,1-ethylene acetal

: 5707-04-0
Phenylselenyl chloride

: 915019-37-3
(1R)-1-(hydroxymethyl)-3-(phenylselenomethyl)-2-oxaspiro[4.5]decan-8-one

Guidance literature:: (R)-4-(1,2-dihydroxyethyl)-4-(prop-2-enyl)cyclohexan-1-one 1,1-ethylene acetal; Phenylselenyl chloride; In dichloromethane; at -78 ℃; for 4h;

With hydrogenchloride; In tetrahydrofuran; at 20 ℃; for 2h;
DOI:10.1248/cpb.54.1138

Reference yield:

: 856680-47-2
(+/-)-2-(hydroxymethyl)-1-oxaspiro[2,5]octan-6-one 6,6-ethylene acetal

: 915019-37-3
(1R)-1-(hydroxymethyl)-3-(phenylselenomethyl)-2-oxaspiro[4.5]decan-8-one

Guidance literature:: Multi-step reaction with 5 steps

1.1: i-Pr₂NEt / CH₂Cl₂ / 20 °C

2.1: ClTi(OPh)3 / tetrahydrofuran / 1 h / -50 °C

2.2: tetrahydrofuran / -50 - 0 °C

3.1: 83 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / 3 h / -60 °C

4.1: (-)-DIP-Cl / 48 h / 20 °C

4.2: 75 percent / H₂O₂; aq. NaOH / tetrahydrofuran / 2 h / 0 °C

5.1: CH₂Cl₂ / 4 h / -78 °C

5.2: 55 percent / aq. HCl / tetrahydrofuran / 2 h / 20 °C

With oxalyl dichloride; titanium monochloride triphenoxide; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; (-)-diisopinocamphenylborane chloride; In tetrahydrofuran; dichloromethane; 3.1: Swern oxidation;
DOI:10.1248/cpb.54.1138

Reference yield:

: 856680-28-9
(+/-)-2-(methoxymethoxymethyl)-1-oxaspiro[2,5]octan-6-one 6,6-ethylene acetal

: 915019-37-3
(1R)-1-(hydroxymethyl)-3-(phenylselenomethyl)-2-oxaspiro[4.5]decan-8-one

Guidance literature:: Multi-step reaction with 4 steps

1.1: ClTi(OPh)3 / tetrahydrofuran / 1 h / -50 °C

1.2: tetrahydrofuran / -50 - 0 °C

2.1: 83 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / 3 h / -60 °C

3.1: (-)-DIP-Cl / 48 h / 20 °C

3.2: 75 percent / H₂O₂; aq. NaOH / tetrahydrofuran / 2 h / 0 °C

4.1: CH₂Cl₂ / 4 h / -78 °C

4.2: 55 percent / aq. HCl / tetrahydrofuran / 2 h / 20 °C

With oxalyl dichloride; titanium monochloride triphenoxide; dimethyl sulfoxide; triethylamine; (-)-diisopinocamphenylborane chloride; In tetrahydrofuran; dichloromethane; 2.1: Swern oxidation;
DOI:10.1248/cpb.54.1138