(R)-3-Hydroxy-3-[(2R,4S,5S)-5-methoxy-2-(4-methoxy-phenyl)-[1,3]dioxan-4-yl]-2,2-dimethyl-propionic acid methyl ester

Base Information

Chemical Name:(R)-3-Hydroxy-3-[(2R,4S,5S)-5-methoxy-2-(4-methoxy-phenyl)-[1,3]dioxan-4-yl]-2,2-dimethyl-propionic acid methyl ester
CAS No.:1054786-44-5
Molecular Formula:C₁₈H₂₆O₇
Molecular Weight:354.4
Hs Code.:

Synonyms:(R)-3-Hydroxy-3-[(2R,4S,5S)-5-methoxy-2-(4-methoxy-phenyl)-[1,3]dioxan-4-yl]-2,2-dimethyl-propionic acid methyl ester

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Chemical Property of (R)-3-Hydroxy-3-[(2R,4S,5S)-5-methoxy-2-(4-methoxy-phenyl)-[1,3]dioxan-4-yl]-2,2-dimethyl-propionic acid methyl ester

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Technology Process of (R)-3-Hydroxy-3-[(2R,4S,5S)-5-methoxy-2-(4-methoxy-phenyl)-[1,3]dioxan-4-yl]-2,2-dimethyl-propionic acid methyl ester

There total 7 articles about (R)-3-Hydroxy-3-[(2R,4S,5S)-5-methoxy-2-(4-methoxy-phenyl)-[1,3]dioxan-4-yl]-2,2-dimethyl-propionic acid methyl 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: 73.0%

: 31469-15-5
1-methoxy-2-methyl-1-trimethylsiloxy-1-propene

: 158226-85-8
(2R,4R,5S)-5-Methoxy-2-(4-methoxy-phenyl)-[1,3]dioxane-4-carbaldehyde

: 1054786-44-5
(R)-3-Hydroxy-3-[(2R,4S,5S)-5-methoxy-2-(4-methoxy-phenyl)-[1,3]dioxan-4-yl]-2,2-dimethyl-propionic acid methyl ester

Guidance literature:: With borane-THF; tosyl derivative of D-valine; In dichloromethane; at -78 ℃; for 4h;
DOI:10.1016/S0040-4039(00)77073-0

Reference yield:

: 2186-92-7
p-Anisaldehyde dimethyl acetal

: 1054786-44-5
(R)-3-Hydroxy-3-[(2R,4S,5S)-5-methoxy-2-(4-methoxy-phenyl)-[1,3]dioxan-4-yl]-2,2-dimethyl-propionic acid methyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 93 percent / p-toluenesulfonic acid / dimethylformamide / 4 h / 40 °C

2: 83 percent / sodium cyanoborohydride, trimethylsilyl triflate / acetonitrile / 2 h / Ambient temperature

3: 91 percent / silver oxide / dimethylformamide / 16 h / 50 °C

4: 87 percent / lithium borohydride / tetrahydrofuran / 0.5 h / Heating

5: 1.) DDQ, 4A molecular sieves; 2.) TsOH / 1.) CH₂Cl₂, rt., 1 h; 2.) toluene, rt., 15 min

6: 90 percent / (COCl)2, DMSO, Et₃N / CH₂Cl₂ / -78 degC, 10 min, 0 degC, 0.5 h

7: 73 percent / tosyl derivative of D-valine, BH₃-THF / CH₂Cl₂ / 4 h / -78 °C

With lithium borohydride; borane-THF; oxalyl dichloride; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; tosyl derivative of D-valine; sodium cyanoborohydride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; silver(l) oxide; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1016/S0040-4039(00)77073-0

Reference yield:

: 68572-75-8
diethyl (4R,5R)-2-(4-methoxyphenyl)-1,3-dioxolane-4,5-dicarboxylate

: 1054786-44-5
(R)-3-Hydroxy-3-[(2R,4S,5S)-5-methoxy-2-(4-methoxy-phenyl)-[1,3]dioxan-4-yl]-2,2-dimethyl-propionic acid methyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 83 percent / sodium cyanoborohydride, trimethylsilyl triflate / acetonitrile / 2 h / Ambient temperature

2: 91 percent / silver oxide / dimethylformamide / 16 h / 50 °C

3: 87 percent / lithium borohydride / tetrahydrofuran / 0.5 h / Heating

4: 1.) DDQ, 4A molecular sieves; 2.) TsOH / 1.) CH₂Cl₂, rt., 1 h; 2.) toluene, rt., 15 min

5: 90 percent / (COCl)2, DMSO, Et₃N / CH₂Cl₂ / -78 degC, 10 min, 0 degC, 0.5 h

6: 73 percent / tosyl derivative of D-valine, BH₃-THF / CH₂Cl₂ / 4 h / -78 °C

With lithium borohydride; borane-THF; oxalyl dichloride; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; tosyl derivative of D-valine; sodium cyanoborohydride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; silver(l) oxide; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1016/S0040-4039(00)77073-0