{(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

Base Information

• Chemical Name: {(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
• CAS No.: 1391853-50-1
• Molecular Formula: C₃₉H₅₂O₄Si
• Molecular Weight: 612.925
• Mol file: 1391853-50-1.mol

Synonyms:

Chemical Property of {(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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of {(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

There total 17 articles about {(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 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:

C18H19NO3S2 (1245726-29-7) + (2S,6R,8S,9S)-8-(tert-butyldiphenylsilyloxymethyl)-9-methyl-1,7-dioxaspiro[5.5]undecane-2-carbaldehyde (1245726-28-6) → {(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 (1245726-30-0) + {(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 (1391853-50-1)

Guidance literature:

C₁₈H₁₉NO₃S₂; With lithium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; for 0.5h; Inert atmosphere;

(2S,6R,8S,9S)-8-(tert-butyldiphenylsilyloxymethyl)-9-methyl-1,7-dioxaspiro[5.5]undecane-2-carbaldehyde; In tetrahydrofuran; at -78 - 60 ℃; for 1.5h; optical yield given as %de; Inert atmosphere;

DOI:10.1002/chem.201102462

Reference yield:

ethyl (2E,4S)-5-(tert-butyldiphenylsilanyloxy)-4-hydroxy-2-pentenoate (885051-17-2) → {(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 (1245726-30-0) + {(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 (1391853-50-1)

Guidance literature:

Multi-step reaction with 11 steps

1.1: pyridinium p-toluenesulfonate / dichloromethane / 16 h / Inert atmosphere; Reflux

2.1: copper(l) iodide / tetrahydrofuran; diethyl ether / 0.25 h / -20 - -10 °C / Inert atmosphere

2.2: 5 h / -78 - -50 °C / Inert atmosphere

3.1: diisobutylaluminium hydride / dichloromethane / 2 h / -78 °C / Inert atmosphere

4.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere

4.2: -78 - 20 °C / Inert atmosphere

5.1: pyridinium p-toluenesulfonate / 1,4-dioxane; water / 4 h / 70 °C

6.1: pyridinium chlorochromate / dichloromethane / 5 h / 20 °C / Inert atmosphere; Molecular sieve

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

7.2: 0.25 h / -78 - 20 °C / Inert atmosphere

8.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 0.67 h / 20 °C / Inert atmosphere

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

10.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.5 h / -78 °C

10.2: 0.5 h / -78 - 20 °C

11.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere

11.2: 1.5 h / -78 - 60 °C / Inert atmosphere

With copper(l) iodide; oxalyl dichloride; boron trifluoride diethyl etherate; sodium hexamethyldisilazane; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; toluene-4-sulfonic acid; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; pyridinium chlorochromate; lithium hexamethyldisilazane; In tetrahydrofuran; 1,4-dioxane; diethyl ether; dichloromethane; water; 10.1: Swern oxidation / 10.2: Swern oxidation;

DOI:10.1002/chem.201102462

Reference yield:

C18H23NO2S2 → {(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 (1245726-30-0) + {(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 (1391853-50-1)

Guidance literature:

Multi-step reaction with 6 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

5.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.5 h / -78 °C

5.2: 0.5 h / -78 - 20 °C

6.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere

6.2: 1.5 h / -78 - 60 °C / Inert atmosphere

With ammonium molybdate; oxalyl dichloride; boron trifluoride diethyl etherate; dihydrogen peroxide; toluene-4-sulfonic acid; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium hexamethyldisilazane; In tetrahydrofuran; ethanol; dichloromethane; water; 5.1: Swern oxidation / 5.2: Swern oxidation;

DOI:10.1002/chem.201102462

upstream raw materials:

ethyl (2E,4S)-5-(tert-butyldiphenylsilanyloxy)-4-hydroxy-2-pentenoate

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