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

Base Information

• Chemical Name: Methyl <1(S)-(1α,3β,4α,5α)>-3-<<(benzyloxy)methyl>oxy>-1-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-4-hydroxy-5-(hydroxymethyl)-cyclohexane-1-carboxylate
• CAS No.: 160911-90-0
• Molecular Formula: C₂₃H₃₈O₇Si
• Molecular Weight: 454.636

Synonyms:

Chemical Property of Methyl <1(S)-(1α,3β,4α,5α)>-3-<<(benzyloxy)methyl>oxy>-1-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-4-hydroxy-5-(hydroxymethyl)-cyclohexane-1-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Methyl <1(S)-(1α,3β,4α,5α)>-3-<<(benzyloxy)methyl>oxy>-1-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-4-hydroxy-5-(hydroxymethyl)-cyclohexane-1-carboxylate

There total 6 articles about Methyl <1(S)-(1α,3β,4α,5α)>-3-<<(benzyloxy)methyl>oxy>-1-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-4-hydroxy-5-(hydroxymethyl)-cyclohexane-1-carboxylate 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) → Methyl <1(S)-(1α,3β,4α,5α)>-3-<<(benzyloxy)methyl>oxy>-1-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-4-hydroxy-5-(hydroxymethyl)-cyclohexane-1-carboxylate (160911-90-0)

Guidance literature:

Multi-step reaction with 5 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

With 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) → Methyl <1(S)-(1α,3β,4α,5α)>-3-<<(benzyloxy)methyl>oxy>-1-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-4-hydroxy-5-(hydroxymethyl)-cyclohexane-1-carboxylate (160911-90-0)

Guidance literature:

Multi-step reaction with 5 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

With 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) → Methyl <1(S)-(1α,3β,4α,5α)>-3-<<(benzyloxy)methyl>oxy>-1-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-4-hydroxy-5-(hydroxymethyl)-cyclohexane-1-carboxylate (160911-90-0)

Guidance literature:

Multi-step reaction with 3 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

With 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:

(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

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

Downstream raw materials:

(1S,3R,4R,5S)-3-Benzyloxymethoxy-1,4-bis-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-cyclohexanecarboxylic acid methyl ester

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

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

Methyl <1(S)-(1α,3β,4α,5α)>-3-<(benzyloxymethyl)oxy>-1,4-bis<<(1,1-dimethylethyl)dimethylsilyl>oxy>-5-<<(triethylsilyl)oxy>ylidene>cyclohexane-1-carboxylate

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