<5R,6S(S)>-6-<3-(tert-butyldiphenylsilyloxy)propyl>-5,6-dihydro-5-methyl-2-pyranone

Base Information

• Chemical Name: <5R,6S(S)>-6-<3-(tert-butyldiphenylsilyloxy)propyl>-5,6-dihydro-5-methyl-2-pyranone
• CAS No.: 142592-69-6
• Molecular Formula: C₂₅H₃₂O₃Si
• Molecular Weight: 408.613
• Mol file: 142592-69-6.mol

Synonyms:<5R,6S(S)>-6-<3-(tert-butyldiphenylsilyloxy)propyl>-5,6-dihydro-5-methyl-2-pyranone

Chemical Property of <5R,6S(S)>-6-<3-(tert-butyldiphenylsilyloxy)propyl>-5,6-dihydro-5-methyl-2-pyranone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of <5R,6S(S)>-6-<3-(tert-butyldiphenylsilyloxy)propyl>-5,6-dihydro-5-methyl-2-pyranone

There total 7 articles about <5R,6S(S)>-6-<3-(tert-butyldiphenylsilyloxy)propyl>-5,6-dihydro-5-methyl-2-pyranone 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:

(R)-3-[(tert-butyldiphenylsilyl)oxy]-2-methylpropanal (91751-24-5,92817-88-4,123284-89-9,112897-04-8) → <5R,6S(S)>-6-<3-(tert-butyldiphenylsilyloxy)propyl>-5,6-dihydro-5-methyl-2-pyranone (142592-69-6)

Guidance literature:

Multi-step reaction with 6 steps

1: 95 percent / CH₂Cl₂ / 5 h / Ambient temperature

2: 96 percent / Dibal-H / toluene / 0.5 h / -78 °C

3: 97 percent / D-(-)-diethyltartrate, Ti(OiPr)4, t-BuOOH / CH₂Cl₂; toluene / -20 °C

4: 1.) Me₂SO, (COCl)2, 2.) Et₂N / 1.) CH₂Cl₂, -78 deg C, 20 min, 2.) -78 deg C to r.t.

5: 1.) hexamethyldisilazane, KH / 1.) THF, toluene, r.t., 2.) -20 deg C to r.t.

6: 1.) Fe₂(CO)9 / 1.) THF, 8 h, 2.) C₆H₆, 90 deg C, 240 atm, 3 d

With titanium(IV) isopropylate; tert.-butylhydroperoxide; oxalyl dichloride; diiron nonacarbonyl; diethyl (2S,3S)-tartrate; potassium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; diethylamine; 1,1,1,3,3,3-hexamethyl-disilazane; In dichloromethane; toluene;

DOI:10.1016/S0040-4020(01)80467-1

Reference yield:

(4S,2E)-5-(tert-butyldiphenylsilyloxy)-2,4-dimethylpent-2-en-1-ol (144604-72-8) → <5R,6S(S)>-6-<3-(tert-butyldiphenylsilyloxy)propyl>-5,6-dihydro-5-methyl-2-pyranone (142592-69-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 97 percent / D-(-)-diethyltartrate, Ti(OiPr)4, t-BuOOH / CH₂Cl₂; toluene / -20 °C

2: 1.) Me₂SO, (COCl)2, 2.) Et₂N / 1.) CH₂Cl₂, -78 deg C, 20 min, 2.) -78 deg C to r.t.

3: 1.) hexamethyldisilazane, KH / 1.) THF, toluene, r.t., 2.) -20 deg C to r.t.

4: 1.) Fe₂(CO)9 / 1.) THF, 8 h, 2.) C₆H₆, 90 deg C, 240 atm, 3 d

With titanium(IV) isopropylate; tert.-butylhydroperoxide; oxalyl dichloride; diiron nonacarbonyl; diethyl (2S,3S)-tartrate; potassium hydride; dimethyl sulfoxide; diethylamine; 1,1,1,3,3,3-hexamethyl-disilazane; In dichloromethane; toluene;

DOI:10.1016/S0040-4020(01)80467-1

Reference yield:

ethyl (2E,4S)-5-(tert-butyldiphenylsilyloxy)-2,4-dimethylpent-2-enoate (142592-66-3) → <5R,6S(S)>-6-<3-(tert-butyldiphenylsilyloxy)propyl>-5,6-dihydro-5-methyl-2-pyranone (142592-69-6)

Guidance literature:

Multi-step reaction with 5 steps

1: 96 percent / Dibal-H / toluene / 0.5 h / -78 °C

2: 97 percent / D-(-)-diethyltartrate, Ti(OiPr)4, t-BuOOH / CH₂Cl₂; toluene / -20 °C

3: 1.) Me₂SO, (COCl)2, 2.) Et₂N / 1.) CH₂Cl₂, -78 deg C, 20 min, 2.) -78 deg C to r.t.

4: 1.) hexamethyldisilazane, KH / 1.) THF, toluene, r.t., 2.) -20 deg C to r.t.

5: 1.) Fe₂(CO)9 / 1.) THF, 8 h, 2.) C₆H₆, 90 deg C, 240 atm, 3 d

With titanium(IV) isopropylate; tert.-butylhydroperoxide; oxalyl dichloride; diiron nonacarbonyl; diethyl (2S,3S)-tartrate; potassium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; diethylamine; 1,1,1,3,3,3-hexamethyl-disilazane; In dichloromethane; toluene;

DOI:10.1016/S0040-4020(01)80467-1

upstream raw materials:

carbon monoxide

<2S,3R(S)>-2-<3-(tert-butyldiphenylsilyloxy)propyl>-2-ethenyl-2-methyloxirane

(R)-3-[(tert-butyldiphenylsilyl)oxy]-2-methylpropanal

(4S,2E)-5-(tert-butyldiphenylsilyloxy)-2,4-dimethylpent-2-en-1-ol

Downstream raw materials:

<5R,6S(S)>-6-<3-(tert-butyldiphenylsilyloxy)propyl>-5-methyltetrahydro-2-pyranone

(βR,2S,3R,6S,8S)-2-<α-(tert-butyldiphenylsilyloxy)ethyl>-8-<2-(benzyloxy)ethyl>-β,3-dimethyl-1,7-dioxaspiro<5.5>undecane

<2RS,5R,6S,(S)>-6-<3-(tert-butyldiphenylsilyloxy)propyl>-5-methyltetrahydro-2-(phenylsulphonyl)-2H-pyran

(βR,2S,3R,6S,8S)-2-[α-(tert-butyldiphenylsilyloxy)ethyl]-β,3-dimethyl-1,7-dioxaspiro[5.5]undecane-8-ethanol