(4R,5S)-5-((S)-2-Hydroxy-1-methoxy-ethyl)-4-(4-methoxy-benzyloxy)-3,3-dimethyl-dihydro-furan-2-one

Base Information

Chemical Name:(4R,5S)-5-((S)-2-Hydroxy-1-methoxy-ethyl)-4-(4-methoxy-benzyloxy)-3,3-dimethyl-dihydro-furan-2-one
CAS No.:158226-89-2
Molecular Formula:C₁₇H₂₄O₆
Molecular Weight:324.374
Hs Code.:

Synonyms:(4R,5S)-5-((S)-2-Hydroxy-1-methoxy-ethyl)-4-(4-methoxy-benzyloxy)-3,3-dimethyl-dihydro-furan-2-one

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Chemical Property of (4R,5S)-5-((S)-2-Hydroxy-1-methoxy-ethyl)-4-(4-methoxy-benzyloxy)-3,3-dimethyl-dihydro-furan-2-one

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Technology Process of (4R,5S)-5-((S)-2-Hydroxy-1-methoxy-ethyl)-4-(4-methoxy-benzyloxy)-3,3-dimethyl-dihydro-furan-2-one

There total 6 articles about (4R,5S)-5-((S)-2-Hydroxy-1-methoxy-ethyl)-4-(4-methoxy-benzyloxy)-3,3-dimethyl-dihydro-furan-2-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: 85.0%

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

: 158226-89-2
(4R,5S)-5-((S)-2-Hydroxy-1-methoxy-ethyl)-4-(4-methoxy-benzyloxy)-3,3-dimethyl-dihydro-furan-2-one

Guidance literature:: With hydrogenchloride; In methanol; at 0 ℃; for 0.25h;
DOI:10.1016/S0040-4039(00)77073-0

Reference yield:

: 158226-82-5
(2S,3S)-2-Methoxy-3-(4-methoxy-benzyloxy)-butane-1,4-diol

: 158226-89-2
(4R,5S)-5-((S)-2-Hydroxy-1-methoxy-ethyl)-4-(4-methoxy-benzyloxy)-3,3-dimethyl-dihydro-furan-2-one

Guidance literature:: Multi-step reaction with 5 steps

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

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

3: 73 percent / tosyl derivative of D-valine, BH₃-THF / CH₂Cl₂ / 4 h / -78 °C

4: 78 percent / sodium hydride / dimethylformamide; tetrahydrofuran / 0.42 h / -5 °C

5: 85 percent / HCl / methanol / 0.25 h / 0 °C

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

Reference yield:

: 158226-81-4
(2R,3R)-2-Methoxy-3-(4-methoxy-benzyloxy)-succinic acid diethyl ester

: 158226-89-2
(4R,5S)-5-((S)-2-Hydroxy-1-methoxy-ethyl)-4-(4-methoxy-benzyloxy)-3,3-dimethyl-dihydro-furan-2-one

Guidance literature:: Multi-step reaction with 6 steps

1: 87 percent / lithium borohydride / tetrahydrofuran / 0.5 h / Heating

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

3: 90 percent / (COCl)2, DMSO, Et₃N / CH₂Cl₂ / -78 degC, 10 min, 0 degC, 0.5 h

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

5: 78 percent / sodium hydride / dimethylformamide; tetrahydrofuran / 0.42 h / -5 °C

6: 85 percent / HCl / methanol / 0.25 h / 0 °C

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