(2S,6S,8S,9S)-8-(tert-butyldiphenylsilyloxymethyl)-9-methyl-1,7-dioxaspiro[5.5]undecane-2-methanol

Base Information

• Chemical Name: (2S,6S,8S,9S)-8-(tert-butyldiphenylsilyloxymethyl)-9-methyl-1,7-dioxaspiro[5.5]undecane-2-methanol
• CAS No.: 1245726-22-0
• Molecular Formula: C₂₈H₄₀O₄Si
• Molecular Weight: 468.709
• Mol file: 1245726-22-0.mol

Synonyms:(2S,6S,8S,9S)-8-(tert-butyldiphenylsilyloxymethyl)-9-methyl-1,7-dioxaspiro[5.5]undecane-2-methanol

Chemical Property of (2S,6S,8S,9S)-8-(tert-butyldiphenylsilyloxymethyl)-9-methyl-1,7-dioxaspiro[5.5]undecane-2-methanol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,6S,8S,9S)-8-(tert-butyldiphenylsilyloxymethyl)-9-methyl-1,7-dioxaspiro[5.5]undecane-2-methanol

There total 13 articles about (2S,6S,8S,9S)-8-(tert-butyldiphenylsilyloxymethyl)-9-methyl-1,7-dioxaspiro[5.5]undecane-2-methanol 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:

C34H48O4Si (1245726-23-1) → (2S,6S,8S,9S)-8-(tert-butyldiphenylsilyloxymethyl)-9-methyl-1,7-dioxaspiro[5.5]undecane-2-methanol (1245726-22-0)

Guidance literature:

With toluene-4-sulfonic acid; In dichloromethane; at 20 ℃; for 0.416667h;

DOI:10.1016/j.tetlet.2010.06.006

Reference yield:

(S)-3-(1,4-dioxaspiro[4.5]decan-2-yl)propyl 4-methylbenzenesulfonate → (2S,6S,8S,9S)-8-(tert-butyldiphenylsilyloxymethyl)-9-methyl-1,7-dioxaspiro[5.5]undecane-2-methanol (1245726-22-0)

Guidance literature:

Multi-step reaction with 5 steps

1.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 °C / Inert atmosphere

1.2: 24 h / 0 - 20 °C / Inert atmosphere

2.1: ammonium molybdate; dihydrogen peroxide / ethanol; water / 24 h / 0 - 20 °C

3.1: boron trifluoride diethyl etherate; lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere

3.2: 0.25 h / -78 - 20 °C / Inert atmosphere

4.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 0.67 h / 20 °C / Inert atmosphere

5.1: toluene-4-sulfonic acid / dichloromethane / 0.42 h / 20 °C / Inert atmosphere

With ammonium molybdate; boron trifluoride diethyl etherate; dihydrogen peroxide; sodium hydride; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium hexamethyldisilazane; In tetrahydrofuran; ethanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1002/chem.201102462

Reference yield:

C18H23NO2S2 → (2S,6S,8S,9S)-8-(tert-butyldiphenylsilyloxymethyl)-9-methyl-1,7-dioxaspiro[5.5]undecane-2-methanol (1245726-22-0)

Guidance literature:

Multi-step reaction with 4 steps

1.1: ammonium molybdate; dihydrogen peroxide / ethanol; water / 24 h / 0 - 20 °C

2.1: boron trifluoride diethyl etherate; lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere

2.2: 0.25 h / -78 - 20 °C / Inert atmosphere

3.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 0.67 h / 20 °C / Inert atmosphere

4.1: toluene-4-sulfonic acid / dichloromethane / 0.42 h / 20 °C / Inert atmosphere

With ammonium molybdate; boron trifluoride diethyl etherate; dihydrogen peroxide; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium hexamethyldisilazane; In tetrahydrofuran; ethanol; dichloromethane; water;

DOI:10.1002/chem.201102462

upstream raw materials:

C₃₄H₄₈O₄Si

ethyl (3S,4S)-5-(tert-butyldiphenylsilyloxy)-3-methyl-4-(tetrahydro-2H-pyran-2-yloxy)pentanoate

tert-butyl[(2S,3S)-6-methoxy-3-methyl-2-(tetrahydro-2H-pyran-2-yloxy)hex-5-enyloxy]diphenylsilane

(5S,6S)-6-(tert-butyldiphenylsilyloxymethyl)-5-methyltetrahydro-2H-pyran-2-one

Downstream raw materials:

(2S,6R,8S,9S)-8-(tert-butyldiphenylsilyloxymethyl)-9-methyl-1,7-dioxaspiro[5.5]undecane-2-carbaldehyde

{(2S,3S,6S,8S)-8-[(S,E)-4-benzyloxy3-methylbut-1-enyl]-3-methyl-1,7-dioxaspiro[5.5]undecane-2-ylmethoxy}(tert-butyl)diphenylsilane

{(2S,3S,6S,8S)-8-[(S,Z)-4-benzyloxy3-methylbut-1-enyl]-3-methyl-1,7-dioxaspiro[5.5]undecane-2-ylmethoxy}(tert-butyl)diphenylsilane