Propylcyclohexanecarboxylate

Base Information

• Chemical Name: Propylcyclohexanecarboxylate
• CAS No.: 87614-59-3
• Molecular Formula: C23H30O3Si
• Molecular Weight: 382.575
• DSSTox Substance ID: DTXSID90698879
• Mol file: 87614-59-3.mol

Synonyms:87614-59-3;propylcyclohexanecarboxylate;DTXSID90698879;1,5-Anhydro-2-(2-{[tert-butyl(diphenyl)silyl]oxy}ethyl)-2,4-dideoxypent-4-enitol

Chemical Property of Propylcyclohexanecarboxylate

Chemical Property:

• Vapor Pressure: 1.58E-09mmHg at 25°C
• Boiling Point: 467.1°C at 760 mmHg
• Flash Point: 236.3°C
• PSA: 38.69000
• Density: 1.09g/cm³
• LogP: 3.47410
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 7
• Exact Mass: 382.19642135
• Heavy Atom Count: 27
• Complexity: 455

Purity/Quality:

3-(2-(TERT-BUTYL-DIPHENYL-SILANYLOXY)-ETHYL)-3,4-DIHYDRO-2H-PYRAN-4-OL 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)[Si](C1=CC=CC=C1)(C2=CC=CC=C2)OCCC3COC=CC3O

Technology Process of Propylcyclohexanecarboxylate

There total 6 articles about Propylcyclohexanecarboxylate 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: 93.0%

(3S,4S)-3-(2-Hydroxy-ethyl)-3,4-dihydro-2H-pyran-4-ol (87614-58-2) + tert-butylchlorodiphenylsilane (58479-61-1) → (3S,4S)-3-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-3,4-dihydro-2H-pyran-4-ol (87614-59-3)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(00)88195-2

Reference yield:

(3S,4R,5R)-2-Bromo-tetrahydro-pyran-3,4,5-triol (528869-25-2) → (3S,4S)-3-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-3,4-dihydro-2H-pyran-4-ol (87614-59-3)

Guidance literature:

Multi-step reaction with 6 steps

1: 1.) Hydrogen, Et₃N 2.) MeONa / 2.) MeOH

2: 1.) HC(OEt)3 / 1.) AcOH / 1.) EtOAc 2.) 250 deg C

3: 82 percent / xylene / 18 h / Heating

4: 81 percent / I₂ / tetrahydrofuran; H₂O / 0 °C

5: 86 percent / NaBH₄ / ethanol

6: 93 percent / imidazole / dimethylformamide

With 1H-imidazole; sodium tetrahydroborate; hydrogen; iodine; sodium methylate; triethylamine; orthoformic acid triethyl ester; acetic acid; In tetrahydrofuran; ethanol; water; N,N-dimethyl-formamide; xylene;

DOI:10.1016/S0040-4039(00)88195-2

Reference yield:

D-Arabinose (50-69-1,58-86-6,65-42-9,147-81-9,609-06-3,1114-34-7,1949-78-6,5328-37-0,10323-20-3,20235-19-2,24259-59-4,25990-60-7,34466-20-1,41247-05-6,53106-52-8,55058-43-0,80952-57-4) → (3S,4S)-3-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-3,4-dihydro-2H-pyran-4-ol (87614-59-3)

Guidance literature:

Multi-step reaction with 7 steps

1: HBr, Ac₂O

2: 1.) Hydrogen, Et₃N 2.) MeONa / 2.) MeOH

3: 1.) HC(OEt)3 / 1.) AcOH / 1.) EtOAc 2.) 250 deg C

4: 82 percent / xylene / 18 h / Heating

5: 81 percent / I₂ / tetrahydrofuran; H₂O / 0 °C

6: 86 percent / NaBH₄ / ethanol

7: 93 percent / imidazole / dimethylformamide

With 1H-imidazole; sodium tetrahydroborate; hydrogen bromide; hydrogen; iodine; sodium methylate; acetic anhydride; triethylamine; orthoformic acid triethyl ester; acetic acid; In tetrahydrofuran; ethanol; water; N,N-dimethyl-formamide; xylene;

DOI:10.1016/S0040-4039(00)88195-2

upstream raw materials:

(3S,4S)-3-(2-Hydroxy-ethyl)-3,4-dihydro-2H-pyran-4-ol

tert-butylchlorodiphenylsilane

(3S,4R,5R)-2-Bromo-tetrahydro-pyran-3,4,5-triol

1,5-anhydro-2,3-dideoxy-D-glycero-pent-2-enitol

Downstream raw materials:

2-{(2S,5R)-5-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-5,6-dihydro-2H-pyran-2-yl}-N,N-dimethyl-acetamide

C₂₅H₄₀O₆

C₃₆H₅₀O₆Si

C₄₀H₄₄O₇Si