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

Base Information

Chemical Name:dimethyl (3S,4R)-2-hydroxy-4-methoxy-6-(4'-methoxybenzyloxy)-3-methylhexylphosphonate
CAS No.:603994-15-6
Molecular Formula:C₁₈H₃₁O₇P
Molecular Weight:390.414
Hs Code.:

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

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Chemical Property of dimethyl (3S,4R)-2-hydroxy-4-methoxy-6-(4'-methoxybenzyloxy)-3-methylhexylphosphonate

Chemical Property:

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Technology Process of dimethyl (3S,4R)-2-hydroxy-4-methoxy-6-(4'-methoxybenzyloxy)-3-methylhexylphosphonate

There total 6 articles about dimethyl (3S,4R)-2-hydroxy-4-methoxy-6-(4'-methoxybenzyloxy)-3-methylhexylphosphonate 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: 85.0%

: 756-79-6
dimethyl methane phosphonate

: 603994-09-8
(2R,3R)-3-methoxy-5-(4'-methoxybenzyloxy)-2-methylpentanal

: 603994-15-6
dimethyl (3S,4R)-2-hydroxy-4-methoxy-6-(4'-methoxybenzyloxy)-3-methylhexylphosphonate

Guidance literature:: dimethyl methane phosphonate; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 0.5h;

(2R,3R)-3-methoxy-5-(4'-methoxybenzyloxy)-2-methylpentanal; In tetrahydrofuran; hexane; at -78 ℃; for 1.66667h;
DOI:10.1016/S0957-4166(03)00372-0

Reference yield:

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

: 603994-15-6
dimethyl (3S,4R)-2-hydroxy-4-methoxy-6-(4'-methoxybenzyloxy)-3-methylhexylphosphonate

Guidance literature:: Multi-step reaction with 4 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: 80 percent / 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: 85 percent / tetrahydrofuran; hexane / 1.67 h / -78 °C

With (-)-B-methoxydiisopinocamphenylborane; osmium(VIII) oxide; n-butyllithium; N-methyl-2-indolinone; potassium tert-butylate; water; sodium hydride; In tetrahydrofuran; hexane; acetone;
DOI:10.1016/S0957-4166(03)00372-0

Reference yield:

: 824-94-2
p-methoxybenzyl chloride

: 603994-15-6
dimethyl (3S,4R)-2-hydroxy-4-methoxy-6-(4'-methoxybenzyloxy)-3-methylhexylphosphonate

Guidance literature:: Multi-step reaction with 6 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: 80 percent / 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: 85 percent / tetrahydrofuran; hexane / 1.67 h / -78 °C

With (-)-B-methoxydiisopinocamphenylborane; osmium(VIII) oxide; 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; acetone; 2.1: Swern oxidation;
DOI:10.1016/S0957-4166(03)00372-0