tert-Butyl 3-{[tert-butyl(dimethyl)silyl]oxy}-6-(dimethoxyphosphoryl)-5-oxohexanoate

Base Information

• Chemical Name: tert-Butyl 3-{[tert-butyl(dimethyl)silyl]oxy}-6-(dimethoxyphosphoryl)-5-oxohexanoate
• CAS No.: 615556-98-4
• Molecular Formula: C18H37O7PSi
• Molecular Weight: 424.547
• DSSTox Substance ID: DTXSID40694083
• Mol file: 615556-98-4.mol

Synonyms:615556-98-4;DTXSID40694083;FT-0653278;A833297;3-[tert-butyl(dimethyl)silyl]oxy-6-dimethoxyphosphoryl-5-oxohexanoic acid tert-butyl ester;tert-butyl 3-[tert-butyl(dimethyl)silyl]oxy-6-dimethoxyphosphoryl-5-oxidanylidene-hexanoate;tert-butyl 3-[tert-butyl(dimethyl)silyl]oxy-6-dimethoxyphosphoryl-5-oxohexanoate;tert-Butyl 3-{[tert-butyl(dimethyl)silyl]oxy}-6-(dimethoxyphosphoryl)-5-oxohexanoate

Chemical Property of tert-Butyl 3-{[tert-butyl(dimethyl)silyl]oxy}-6-(dimethoxyphosphoryl)-5-oxohexanoate

Chemical Property:

• PSA: 97.94000
• LogP: 4.55370
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 13
• Exact Mass: 424.20461705
• Heavy Atom Count: 27
• Complexity: 553

Purity/Quality:

97% ^*data from raw suppliers

TERT-BUTYL (3R)-3-[TERT-BUTYL(DIMETHYL)SILYL]OXY-6-DIMETHOXYPHOSPHORYL-5-OXOHEXANOATE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)CC(CC(=O)CP(=O)(OC)OC)O[Si](C)(C)C(C)(C)C

Technology Process of tert-Butyl 3-{[tert-butyl(dimethyl)silyl]oxy}-6-(dimethoxyphosphoryl)-5-oxohexanoate

There total 6 articles about tert-Butyl 3-{[tert-butyl(dimethyl)silyl]oxy}-6-(dimethoxyphosphoryl)-5-oxohexanoate 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: 92.6%

C21H34O5Si + dimethyl methane phosphonate (756-79-6) → tert-butyl (3R)-3-(tert-butyldimethylsilyloxy)-6-dimethoxyphosphinyl-5-oxohexanate (615556-98-4)

Guidance literature:

C₂₁H₃₄O₅Si; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 1h; Inert atmosphere;

dimethyl methane phosphonate; In tetrahydrofuran; hexane; at -78 ℃; Inert atmosphere;

Reference yield: 85.0%

C17H35NO5Si (1073439-79-8) + dimethyl methane phosphonate (756-79-6) → tert-butyl (3R)-3-(tert-butyldimethylsilyloxy)-6-dimethoxyphosphinyl-5-oxohexanate (615556-98-4)

Guidance literature:

dimethyl methane phosphonate; With n-butyllithium; In tetrahydrofuran; hexane; at -90 - -80 ℃; for 2 - 4h;

C₁₇H₃₅NO₅Si; In tetrahydrofuran; hexane; at -90 - -75 ℃; for 1 - 3h;

Reference yield:

(3S)-5-ethoxy-3-hydroxy-5-oxopentanoic acid (95310-87-5) → tert-butyl (3R)-3-(tert-butyldimethylsilyloxy)-6-dimethoxyphosphinyl-5-oxohexanate (615556-98-4)

Guidance literature:

Multi-step reaction with 5 steps

1.1: thionyl chloride / dichloromethane / 0 - 20 °C

2.1: dichloromethane / 20 °C

3.1: sodium hydroxide; methanol / 20 °C

4.1: dicyclohexyl-carbodiimide / dichloromethane / 25 °C

5.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C / Inert atmosphere

5.2: -78 °C / Inert atmosphere

With methanol; n-butyllithium; thionyl chloride; dicyclohexyl-carbodiimide; sodium hydroxide; In tetrahydrofuran; hexane; dichloromethane;

upstream raw materials:

C₁₇H₃₅NO₅Si

dimethyl methane phosphonate

(3S)-5-ethoxy-3-hydroxy-5-oxopentanoic acid

1-tert-butyl 5-ethyl 3-hydroxypentanedioate

Downstream raw materials:

rosuvastatin tert-butyl ester

tertiary butyl 7-[4-(4-fluorophenyl)-6-isopropyl-2-(N-methyl-N-methylsulfonylamino)pyrimidin-5-yl]-(3R)-3-(tert-butyldimethylsilyloxy)-5-oxo-(E)-6-heptenoate