(1S,3R,4R,5S)-4-Acetoxy-3-benzyloxymethoxy-5-[2-(dimethoxy-phosphoryl)-ethyl]-1-hydroxy-cyclohexanecarboxylic acid methyl ester

Base Information

Chemical Name:(1S,3R,4R,5S)-4-Acetoxy-3-benzyloxymethoxy-5-[2-(dimethoxy-phosphoryl)-ethyl]-1-hydroxy-cyclohexanecarboxylic acid methyl ester
CAS No.:1054629-18-3
Molecular Formula:C₂₂H₃₃O₁₀P
Molecular Weight:488.472
Hs Code.:

Synonyms:(1S,3R,4R,5S)-4-Acetoxy-3-benzyloxymethoxy-5-[2-(dimethoxy-phosphoryl)-ethyl]-1-hydroxy-cyclohexanecarboxylic acid methyl ester

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Chemical Property of (1S,3R,4R,5S)-4-Acetoxy-3-benzyloxymethoxy-5-[2-(dimethoxy-phosphoryl)-ethyl]-1-hydroxy-cyclohexanecarboxylic acid methyl ester

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Technology Process of (1S,3R,4R,5S)-4-Acetoxy-3-benzyloxymethoxy-5-[2-(dimethoxy-phosphoryl)-ethyl]-1-hydroxy-cyclohexanecarboxylic acid methyl ester

There total 13 articles about (1S,3R,4R,5S)-4-Acetoxy-3-benzyloxymethoxy-5-[2-(dimethoxy-phosphoryl)-ethyl]-1-hydroxy-cyclohexanecarboxylic 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:

: 160911-99-9
Methyl <1(S)-(1α,3β,4α,5α)>-4-(acetyloxy)-3-<<(benzyloxy)methyl>oxy>-1-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-5-<2-(dimethoxyphosphinyl)ethyl>cyclohexane-1-carboxylate

: 1054629-18-3
(1S,3R,4R,5S)-4-Acetoxy-3-benzyloxymethoxy-5-[2-(dimethoxy-phosphoryl)-ethyl]-1-hydroxy-cyclohexanecarboxylic acid methyl ester

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 ℃; for 0.25h;
DOI:10.1021/jo00102a025

Reference yield:

: 105539-80-8
methyl<1(R)-(1α,4α,5β)>-4-(benzoyloxy)-1-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-5-hydroxy-2-cyclohexene-1-carboxylate

: 1054629-18-3
(1S,3R,4R,5S)-4-Acetoxy-3-benzyloxymethoxy-5-[2-(dimethoxy-phosphoryl)-ethyl]-1-hydroxy-cyclohexanecarboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 12 steps

1: 97 percent / i-Pr₂NEt / CH₂Cl₂ / 15 h / Ambient temperature

2: 72 percent / MeONa / tetrahydrofuran; methanol / 0.25 h / Ambient temperature

3: Et₃N / CH₂Cl₂ / 1.) -78 deg C, 30 min, 2.) r.t., 12 h

4: 78 percent / Bu₃SnH, AIBN / benzene / 18 h / Heating

5: 74 percent / 1.5percent aq. HCl / tetrahydrofuran / 24 h / Ambient temperature

6: 100 percent / NaBH₄ / methanol / 0.08 h / 0 °C

7: 84 percent / Et₃N / CH₂Cl₂ / 12 h / Ambient temperature

8: 87 percent / DMAP, pyridine / 22 h / Ambient temperature

9: p-TsOH monohydrate / methanol / 1.5 h / Ambient temperature

10: CBr₄, PPh₃ / tetrahydrofuran / 2.5 h / Ambient temperature

11: 75 percent / 24 h / Heating

12: Bu₄N(+)F(-) / tetrahydrofuran / 0.25 h / 0 °C

With pyridine; hydrogenchloride; dmap; sodium tetrahydroborate; 2,2'-azobis(isobutyronitrile); carbon tetrabromide; tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; sodium methylate; toluene-4-sulfonic acid; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane; benzene;
DOI:10.1021/jo00102a025

Reference yield:

: 160911-88-6
Methyl <1(R)-(1α,4α,5β)>-5-<<(benzyloxy)methyl>oxy>-1-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-4-hydroxy-2-cyclohexene-1-carboxylate

: 1054629-18-3
(1S,3R,4R,5S)-4-Acetoxy-3-benzyloxymethoxy-5-[2-(dimethoxy-phosphoryl)-ethyl]-1-hydroxy-cyclohexanecarboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 10 steps

1: Et₃N / CH₂Cl₂ / 1.) -78 deg C, 30 min, 2.) r.t., 12 h

2: 78 percent / Bu₃SnH, AIBN / benzene / 18 h / Heating

3: 74 percent / 1.5percent aq. HCl / tetrahydrofuran / 24 h / Ambient temperature

4: 100 percent / NaBH₄ / methanol / 0.08 h / 0 °C

5: 84 percent / Et₃N / CH₂Cl₂ / 12 h / Ambient temperature

6: 87 percent / DMAP, pyridine / 22 h / Ambient temperature

7: p-TsOH monohydrate / methanol / 1.5 h / Ambient temperature

8: CBr₄, PPh₃ / tetrahydrofuran / 2.5 h / Ambient temperature

9: 75 percent / 24 h / Heating

10: Bu₄N(+)F(-) / tetrahydrofuran / 0.25 h / 0 °C

With pyridine; hydrogenchloride; dmap; sodium tetrahydroborate; 2,2'-azobis(isobutyronitrile); carbon tetrabromide; tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; toluene-4-sulfonic acid; triethylamine; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane; benzene;
DOI:10.1021/jo00102a025