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

Base Information

• Chemical Name: Methyl <1(S)-(1α,3β,4α,5α)>-4-(acetyloxy)-3-<<(benzyloxy)methyl>oxy>-1-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-5-<2-<<(1,1-dimethylethyl)dimethylsilyl>oxy>ethyl>cyclohexane-1-carboxylate
• CAS No.: 160911-97-7
• Molecular Formula: C₃₂H₅₆O₈Si₂
• Molecular Weight: 624.963

Synonyms:

Chemical Property of Methyl <1(S)-(1α,3β,4α,5α)>-4-(acetyloxy)-3-<<(benzyloxy)methyl>oxy>-1-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-5-<2-<<(1,1-dimethylethyl)dimethylsilyl>oxy>ethyl>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)>-4-(acetyloxy)-3-<<(benzyloxy)methyl>oxy>-1-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-5-<2-<<(1,1-dimethylethyl)dimethylsilyl>oxy>ethyl>cyclohexane-1-carboxylate

There total 9 articles about Methyl <1(S)-(1α,3β,4α,5α)>-4-(acetyloxy)-3-<<(benzyloxy)methyl>oxy>-1-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-5-<2-<<(1,1-dimethylethyl)dimethylsilyl>oxy>ethyl>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:

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)>-4-(acetyloxy)-3-<<(benzyloxy)methyl>oxy>-1-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-5-<2-<<(1,1-dimethylethyl)dimethylsilyl>oxy>ethyl>cyclohexane-1-carboxylate (160911-97-7)

Guidance literature:

Multi-step reaction with 8 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

With pyridine; hydrogenchloride; dmap; sodium tetrahydroborate; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; sodium methylate; 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)>-4-(acetyloxy)-3-<<(benzyloxy)methyl>oxy>-1-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-5-<2-<<(1,1-dimethylethyl)dimethylsilyl>oxy>ethyl>cyclohexane-1-carboxylate (160911-97-7)

Guidance literature:

Multi-step reaction with 6 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

With pyridine; hydrogenchloride; dmap; sodium tetrahydroborate; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; triethylamine; In tetrahydrofuran; methanol; dichloromethane; benzene;

DOI:10.1021/jo00102a025

Reference yield:

(3aS,5S,7R,7aR)-7-Benzyloxymethoxy-5-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-octahydro-benzofuran-5-carboxylic acid methyl ester → Methyl <1(S)-(1α,3β,4α,5α)>-4-(acetyloxy)-3-<<(benzyloxy)methyl>oxy>-1-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-5-<2-<<(1,1-dimethylethyl)dimethylsilyl>oxy>ethyl>cyclohexane-1-carboxylate (160911-97-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 100 percent / NaBH₄ / methanol / 0.08 h / 0 °C

2: 84 percent / Et₃N / CH₂Cl₂ / 12 h / Ambient temperature

3: 87 percent / DMAP, pyridine / 22 h / Ambient temperature

With pyridine; dmap; sodium tetrahydroborate; triethylamine; In methanol; dichloromethane;

DOI:10.1021/jo00102a025

upstream raw materials:

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

(1S,3R,4R,5R)-3-Benzyloxymethoxy-1-(tert-butyl-dimethyl-silanyloxy)-4-hydroxy-5-(2-hydroxy-ethyl)-cyclohexanecarboxylic acid methyl ester

(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:

(1S,3R,4R,5R)-4-Acetoxy-3-benzyloxymethoxy-1-(tert-butyl-dimethyl-silanyloxy)-5-(2-hydroxy-ethyl)-cyclohexanecarboxylic acid methyl ester

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

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

Methyl <1(S)-(1α,3β,4α,5α)>-4-(acetyloxy)-3-<<(benzyloxy)methyl>oxy>-1-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-5-(2-bromoethyl)cyclohexane-1-carboxylate

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