(1S,3R,4R,5S)-4-Acetoxy-3-benzyloxymethoxy-1-(tert-butyl-dimethyl-silanyloxy)-5-(toluene-4-sulfonyloxymethyl)-cyclohexanecarboxylic acid methyl ester

Base Information

• Chemical Name: (1S,3R,4R,5S)-4-Acetoxy-3-benzyloxymethoxy-1-(tert-butyl-dimethyl-silanyloxy)-5-(toluene-4-sulfonyloxymethyl)-cyclohexanecarboxylic acid methyl ester
• CAS No.: 160912-02-7
• Molecular Formula: C₃₂H₄₆O₁₀SSi
• Molecular Weight: 650.863

Synonyms:(1S,3R,4R,5S)-4-Acetoxy-3-benzyloxymethoxy-1-(tert-butyl-dimethyl-silanyloxy)-5-(toluene-4-sulfonyloxymethyl)-cyclohexanecarboxylic acid methyl ester

Chemical Property of (1S,3R,4R,5S)-4-Acetoxy-3-benzyloxymethoxy-1-(tert-butyl-dimethyl-silanyloxy)-5-(toluene-4-sulfonyloxymethyl)-cyclohexanecarboxylic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

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MSDS Files:

Useful:

Technology Process of (1S,3R,4R,5S)-4-Acetoxy-3-benzyloxymethoxy-1-(tert-butyl-dimethyl-silanyloxy)-5-(toluene-4-sulfonyloxymethyl)-cyclohexanecarboxylic acid methyl ester

There total 7 articles about (1S,3R,4R,5S)-4-Acetoxy-3-benzyloxymethoxy-1-(tert-butyl-dimethyl-silanyloxy)-5-(toluene-4-sulfonyloxymethyl)-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:

Benzyloxymethyl chloride (3587-60-8) → (1S,3R,4R,5S)-4-Acetoxy-3-benzyloxymethoxy-1-(tert-butyl-dimethyl-silanyloxy)-5-(toluene-4-sulfonyloxymethyl)-cyclohexanecarboxylic acid methyl ester (160912-02-7)

Guidance literature:

Multi-step reaction with 7 steps

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

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

3: 97 percent / Et₃N / CH₂Cl₂ / 1 h / 0 °C

4: Bu₃SnH, AIBN / benzene / 17 h / Heating

5: 30percent aq. H₂O₂, NaHCO₃ / methanol; tetrahydrofuran / 5 h / Heating

6: pyridine / 16 h / Ambient temperature

7: pyridine / 18 h / Ambient temperature

With pyridine; 2,2'-azobis(isobutyronitrile); dihydrogen peroxide; tri-n-butyl-tin hydride; sodium methylate; sodium hydrogencarbonate; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; dichloromethane; benzene;

DOI:10.1021/jo00102a025

Reference yield:

methyl<1(R)-(1α,4α,5β)>-4-(benzoyloxy)-1-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-5-hydroxy-2-cyclohexene-1-carboxylate (105539-80-8) → (1S,3R,4R,5S)-4-Acetoxy-3-benzyloxymethoxy-1-(tert-butyl-dimethyl-silanyloxy)-5-(toluene-4-sulfonyloxymethyl)-cyclohexanecarboxylic acid methyl ester (160912-02-7)

Guidance literature:

Multi-step reaction with 7 steps

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

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

3: 97 percent / Et₃N / CH₂Cl₂ / 1 h / 0 °C

4: Bu₃SnH, AIBN / benzene / 17 h / Heating

5: 30percent aq. H₂O₂, NaHCO₃ / methanol; tetrahydrofuran / 5 h / Heating

6: pyridine / 16 h / Ambient temperature

7: pyridine / 18 h / Ambient temperature

With pyridine; 2,2'-azobis(isobutyronitrile); dihydrogen peroxide; tri-n-butyl-tin hydride; sodium methylate; sodium hydrogencarbonate; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; dichloromethane; benzene;

DOI:10.1021/jo00102a025

Reference yield:

Methyl <1(R)-(1α,4α,5β)>-5-<<(benzyloxy)methyl>oxy>-1-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-4-hydroxy-2-cyclohexene-1-carboxylate (160911-88-6) → (1S,3R,4R,5S)-4-Acetoxy-3-benzyloxymethoxy-1-(tert-butyl-dimethyl-silanyloxy)-5-(toluene-4-sulfonyloxymethyl)-cyclohexanecarboxylic acid methyl ester (160912-02-7)

Guidance literature:

Multi-step reaction with 5 steps

1: 97 percent / Et₃N / CH₂Cl₂ / 1 h / 0 °C

2: Bu₃SnH, AIBN / benzene / 17 h / Heating

3: 30percent aq. H₂O₂, NaHCO₃ / methanol; tetrahydrofuran / 5 h / Heating

4: pyridine / 16 h / Ambient temperature

5: pyridine / 18 h / Ambient temperature

With pyridine; 2,2'-azobis(isobutyronitrile); dihydrogen peroxide; tri-n-butyl-tin hydride; sodium hydrogencarbonate; triethylamine; In tetrahydrofuran; methanol; dichloromethane; benzene;

DOI:10.1021/jo00102a025

upstream raw materials:

Benzyloxymethyl chloride

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

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

(3aR,5S,7R,7aR)-7-Benzyloxymethoxy-5-(tert-butyl-dimethyl-silanyloxy)-2,2-dimethyl-octahydro-benzo[d][1,2]oxasilole-5-carboxylic acid methyl ester

Downstream raw materials:

Methyl <1(S)-(1α,3β,4α,5α)>-4-(acetyloxy)-3-<<(benzyloxy)methyl>oxy>-1-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-5-(iodomethyl)cyclohexane-1-carboxylate

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