((1R,3R,4R)-4-Benzyloxy-3-methoxy-cyclohexylmethoxy)-tert-butyl-dimethyl-silane

Base Information

• Chemical Name: ((1R,3R,4R)-4-Benzyloxy-3-methoxy-cyclohexylmethoxy)-tert-butyl-dimethyl-silane
• CAS No.: 129952-26-7
• Molecular Formula: C₂₁H₃₆O₃Si
• Molecular Weight: 364.601
• Mol file: 129952-26-7.mol

Synonyms:((1R,3R,4R)-4-Benzyloxy-3-methoxy-cyclohexylmethoxy)-tert-butyl-dimethyl-silane

Chemical Property of ((1R,3R,4R)-4-Benzyloxy-3-methoxy-cyclohexylmethoxy)-tert-butyl-dimethyl-silane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ((1R,3R,4R)-4-Benzyloxy-3-methoxy-cyclohexylmethoxy)-tert-butyl-dimethyl-silane

There total 12 articles about ((1R,3R,4R)-4-Benzyloxy-3-methoxy-cyclohexylmethoxy)-tert-butyl-dimethyl-silane 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: 92.0%

Dithiocarbonic acid O-[(1R,2S,3R,6S)-3-benzyloxy-6-(tert-butyl-dimethyl-silanyloxymethyl)-2-methoxy-cyclohexyl] ester S-methyl ester (129952-25-6) → ((1R,3R,4R)-4-Benzyloxy-3-methoxy-cyclohexylmethoxy)-tert-butyl-dimethyl-silane (129952-26-7)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In toluene; at 110 ℃; for 2h;

DOI:10.1016/S0040-4039(00)89010-3

Reference yield:

(E)-(2R,3R)-2-Methoxy-8-trimethylsilanyl-oct-6-ene-1,3-diol (129952-17-6) → ((1R,3R,4R)-4-Benzyloxy-3-methoxy-cyclohexylmethoxy)-tert-butyl-dimethyl-silane (129952-26-7)

Guidance literature:

Multi-step reaction with 9 steps

1: 96 percent / imidazole / CH₂Cl₂ / 18 h / 20 °C

2: 73 percent / NaH / dimethylformamide / 18 h / 0 to 20 deg C

3: 84 percent / pyridinium p-toluenesulfonate / methanol / 3.5 h / 50 °C

4: DMSO, (COCl)2, NEt₃ / CH₂Cl₂ / 1 h / -60 °C

5: BF₃-Et₂O / CH₂Cl₂ / 0.75 h / -78 °C

6: 1.) O₃, 2.) NaBH₄ / 1.) CH₂Cl₂, MeOH, -78 deg C, 2.) H₂O, MeOH, 0 to 40 deg C, 3 h

7: 88 percent / imidazole / CH₂Cl₂ / 18 h / 20 °C

8: 87 percent / NaH / 3.5 h / 70 °C

9: 92 percent / Bu₃SnH, AIBN / toluene / 2 h / 110 °C

With 1H-imidazole; sodium tetrahydroborate; oxalyl dichloride; 2,2'-azobis(isobutyronitrile); boron trifluoride diethyl etherate; tri-n-butyl-tin hydride; pyridinium p-toluenesulfonate; sodium hydride; ozone; dimethyl sulfoxide; triethylamine; In methanol; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1016/S0040-4039(00)89010-3

Reference yield:

(E)-(2S,3R)-3-Hydroxy-2-methoxy-8-trimethylsilanyl-oct-6-enoic acid methyl ester (129952-16-5) → ((1R,3R,4R)-4-Benzyloxy-3-methoxy-cyclohexylmethoxy)-tert-butyl-dimethyl-silane (129952-26-7)

Guidance literature:

Multi-step reaction with 10 steps

1: 84 percent / LiAlH₄ / diethyl ether / 3 h / 0 to 20 deg C

2: 96 percent / imidazole / CH₂Cl₂ / 18 h / 20 °C

3: 73 percent / NaH / dimethylformamide / 18 h / 0 to 20 deg C

4: 84 percent / pyridinium p-toluenesulfonate / methanol / 3.5 h / 50 °C

5: DMSO, (COCl)2, NEt₃ / CH₂Cl₂ / 1 h / -60 °C

6: BF₃-Et₂O / CH₂Cl₂ / 0.75 h / -78 °C

7: 1.) O₃, 2.) NaBH₄ / 1.) CH₂Cl₂, MeOH, -78 deg C, 2.) H₂O, MeOH, 0 to 40 deg C, 3 h

8: 88 percent / imidazole / CH₂Cl₂ / 18 h / 20 °C

9: 87 percent / NaH / 3.5 h / 70 °C

10: 92 percent / Bu₃SnH, AIBN / toluene / 2 h / 110 °C

With 1H-imidazole; sodium tetrahydroborate; lithium aluminium tetrahydride; oxalyl dichloride; 2,2'-azobis(isobutyronitrile); boron trifluoride diethyl etherate; tri-n-butyl-tin hydride; pyridinium p-toluenesulfonate; sodium hydride; ozone; dimethyl sulfoxide; triethylamine; In methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1016/S0040-4039(00)89010-3

upstream raw materials:

Dithiocarbonic acid O-[(1R,2S,3R,6S)-3-benzyloxy-6-(tert-butyl-dimethyl-silanyloxymethyl)-2-methoxy-cyclohexyl] ester S-methyl ester

(E)-(2R,3R)-2-Methoxy-8-trimethylsilanyl-oct-6-ene-1,3-diol

(E)-(2S,3R)-3-Hydroxy-2-methoxy-8-trimethylsilanyl-oct-6-enoic acid methyl ester

(E)-(2R,3R)-1-(tert-Butyl-dimethyl-silanyloxy)-2-methoxy-8-trimethylsilanyl-oct-6-en-3-ol