dimethyl (3S,4S)-4-methoxy-6-(4'-methoxybenzyloxy)-3-methyl-2-oxohexylphosphonate

Base Information

Chemical Name:dimethyl (3S,4S)-4-methoxy-6-(4'-methoxybenzyloxy)-3-methyl-2-oxohexylphosphonate
CAS No.:603994-17-8
Molecular Formula:C₁₈H₂₉O₇P
Molecular Weight:388.398
Hs Code.:

Synonyms:dimethyl (3S,4S)-4-methoxy-6-(4'-methoxybenzyloxy)-3-methyl-2-oxohexylphosphonate

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Chemical Property of dimethyl (3S,4S)-4-methoxy-6-(4'-methoxybenzyloxy)-3-methyl-2-oxohexylphosphonate

Chemical Property:

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Technology Process of dimethyl (3S,4S)-4-methoxy-6-(4'-methoxybenzyloxy)-3-methyl-2-oxohexylphosphonate

There total 7 articles about dimethyl (3S,4S)-4-methoxy-6-(4'-methoxybenzyloxy)-3-methyl-2-oxohexylphosphonate 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:

: 603994-16-7
dimethyl (3R,4S)-2-hydroxy-4-methoxy-6-(4'-methoxybenzyloxy)-3-methylhexylphosphonate

: 603994-17-8
dimethyl (3S,4S)-4-methoxy-6-(4'-methoxybenzyloxy)-3-methyl-2-oxohexylphosphonate

Guidance literature:: With dipyridinium dichromate; In N,N-dimethyl-formamide; at 20 ℃; for 5h;
DOI:10.1016/S0957-4166(03)00372-0

Reference yield:

: 128461-65-4
3-(p-methoxybenzyloxy)propanal

: 603994-17-8
dimethyl (3S,4S)-4-methoxy-6-(4'-methoxybenzyloxy)-3-methyl-2-oxohexylphosphonate

Guidance literature:: Multi-step reaction with 5 steps

1.1: tert-BuOK; n-BuLi; (+)-B-methoxydiisopinocampheylborane / tetrahydrofuran; hexane / -78 - -45 °C

1.2: BF₃*Et₂O / tetrahydrofuran; hexane / 4 h / -78 °C

1.3: aq. NaOH; H₂O₂ / tetrahydrofuran; hexane / 25 °C

2.1: NaH / tetrahydrofuran / 2 h / 20 °C

3.1: OsO₄; NMO; H₂O / acetone / 20 °C

3.2: H₅IO₆; H₂O / acetone / 0.5 h

4.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C

4.2: tetrahydrofuran; hexane / 1.67 h / -78 °C

5.1: pyridinium dichromate / dimethylformamide / 5 h / 20 °C

With (+)-Ipc₂BOMe; osmium(VIII) oxide; dipyridinium dichromate; n-butyllithium; N-methyl-2-indolinone; potassium tert-butylate; water; sodium hydride; In tetrahydrofuran; hexane; N,N-dimethyl-formamide; acetone;
DOI:10.1016/S0957-4166(03)00372-0

Reference yield:

: 824-94-2
p-methoxybenzyl chloride

: 603994-17-8
dimethyl (3S,4S)-4-methoxy-6-(4'-methoxybenzyloxy)-3-methyl-2-oxohexylphosphonate

Guidance literature:: Multi-step reaction with 7 steps

1.1: 70 percent / NaH; Bu₄NI / 0 - 20 °C

2.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

3.1: tert-BuOK; n-BuLi; (+)-B-methoxydiisopinocampheylborane / tetrahydrofuran; hexane / -78 - -45 °C

3.2: BF₃*Et₂O / tetrahydrofuran; hexane / 4 h / -78 °C

3.3: aq. NaOH; H₂O₂ / tetrahydrofuran; hexane / 25 °C

4.1: NaH / tetrahydrofuran / 2 h / 20 °C

5.1: OsO₄; NMO; H₂O / acetone / 20 °C

5.2: H₅IO₆; H₂O / acetone / 0.5 h

6.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C

6.2: tetrahydrofuran; hexane / 1.67 h / -78 °C

7.1: pyridinium dichromate / dimethylformamide / 5 h / 20 °C

With (+)-Ipc₂BOMe; osmium(VIII) oxide; dipyridinium dichromate; n-butyllithium; N-methyl-2-indolinone; oxalyl dichloride; potassium tert-butylate; water; tetra-(n-butyl)ammonium iodide; sodium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; acetone; 2.1: Swern oxidation;
DOI:10.1016/S0957-4166(03)00372-0