(4S)-(-)-trans-2-(4-nitrophenoxy)-2-oxo-4-(3-chlorophenyl)-1,3,2-dioxaphosphorinane

Base Information

Chemical Name:(4S)-(-)-trans-2-(4-nitrophenoxy)-2-oxo-4-(3-chlorophenyl)-1,3,2-dioxaphosphorinane
CAS No.:693223-08-4
Molecular Formula:C₁₅H₁₃ClNO₆P
Molecular Weight:369.698
Hs Code.:

Synonyms:(4S)-(-)-trans-2-(4-nitrophenoxy)-2-oxo-4-(3-chlorophenyl)-1,3,2-dioxaphosphorinane

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Chemical Property of (4S)-(-)-trans-2-(4-nitrophenoxy)-2-oxo-4-(3-chlorophenyl)-1,3,2-dioxaphosphorinane

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Technology Process of (4S)-(-)-trans-2-(4-nitrophenoxy)-2-oxo-4-(3-chlorophenyl)-1,3,2-dioxaphosphorinane

There total 11 articles about (4S)-(-)-trans-2-(4-nitrophenoxy)-2-oxo-4-(3-chlorophenyl)-1,3,2-dioxaphosphorinane 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: 78.3%

: 100-02-7,78813-13-5,89830-32-0
4-nitro-phenol

: 777-52-6
1-dichlorophosphoryloxy-4-nitro-benzene

: 625095-57-0
(S)-(-)-1-(3-Chlorophenyl)-1,3-propanediol

: 693223-08-4
(4S)-(-)-trans-2-(4-nitrophenoxy)-2-oxo-4-(3-chlorophenyl)-1,3,2-dioxaphosphorinane

Guidance literature:: 1-dichlorophosphoryloxy-4-nitro-benzene; (S)-(-)-1-(3-Chlorophenyl)-1,3-propanediol; With triethylamine; In tetrahydrofuran; at 0 ℃; for 2h;

4-nitro-phenol; With triethylamine; In tetrahydrofuran; at 20 ℃; optical yield given as %de; diastereoselective reaction;
DOI:10.1111/j.1747-0285.2010.01077.x

Reference yield:

: 51699-45-7
(S)-(-)-1-(3'-Chlorophenyl)-1,3-Propanediol

: 693223-08-4
(4S)-(-)-trans-2-(4-nitrophenoxy)-2-oxo-4-(3-chlorophenyl)-1,3,2-dioxaphosphorinane

Guidance literature:: Multi-step reaction with 4 steps

1.1: 100 percent / trimethylsilyl triflate / tetrahydrofuran / 1 h / 20 °C

2.1: 7.50 g / trimethylsilyltriflate / CH₂Cl₂ / 48 h / -50 °C

3.1: aq. HCl / methanol / 20 °C

4.1: TEA / tetrahydrofuran

4.2: TEA; 4-nitrophenol / tetrahydrofuran

With hydrogenchloride; trimethylsilyl trifluoromethanesulfonate; TEA; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1021/ja031818y

Reference yield:

: 99-02-5
3'-Chloroacetophenone

: 693223-08-4
(4S)-(-)-trans-2-(4-nitrophenoxy)-2-oxo-4-(3-chlorophenyl)-1,3,2-dioxaphosphorinane

Guidance literature:: Multi-step reaction with 4 steps

1.1: 75 percent / DBU / 20 h / 20 °C

2.1: 65 percent / (-)-DIP-Cl / CH₂Cl₂ / -20 - -10 °C

3.1: 88 percent / LiAlH₄ / tetrahydrofuran / 2 h / 20 °C

4.1: TEA / tetrahydrofuran

4.2: TEA; 4-nitrophenol / tetrahydrofuran

With lithium aluminium tetrahydride; TEA; 1,8-diazabicyclo[5.4.0]undec-7-ene; (-)-diisopinocamphenylborane chloride; In tetrahydrofuran; dichloromethane;
DOI:10.1021/ja031818y