{(1S,2S,4R)-2,4-Bis-(tert-butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-diphenyl-silanyloxy)-eth-(Z)-ylidene]-cyclohexyl}-methanol

Base Information

• Chemical Name: {(1S,2S,4R)-2,4-Bis-(tert-butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-diphenyl-silanyloxy)-eth-(Z)-ylidene]-cyclohexyl}-methanol
• CAS No.: 146175-86-2
• Molecular Formula: C₃₇H₆₂O₄Si₃
• Molecular Weight: 655.153
• Mol file: 146175-86-2.mol

Synonyms:{(1S,2S,4R)-2,4-Bis-(tert-butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-diphenyl-silanyloxy)-eth-(Z)-ylidene]-cyclohexyl}-methanol

Chemical Property of {(1S,2S,4R)-2,4-Bis-(tert-butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-diphenyl-silanyloxy)-eth-(Z)-ylidene]-cyclohexyl}-methanol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of {(1S,2S,4R)-2,4-Bis-(tert-butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-diphenyl-silanyloxy)-eth-(Z)-ylidene]-cyclohexyl}-methanol

There total 19 articles about {(1S,2S,4R)-2,4-Bis-(tert-butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-diphenyl-silanyloxy)-eth-(Z)-ylidene]-cyclohexyl}-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: 71.0%

2-[(2S,3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-hydroxymethyl-cyclohex-(Z)-ylidene]-ethanol (146175-85-1) + tert-butylchlorodiphenylsilane (58479-61-1) → {(1S,2S,4R)-2,4-Bis-(tert-butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-diphenyl-silanyloxy)-eth-(Z)-ylidene]-cyclohexyl}-methanol (146175-86-2)

Guidance literature:

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

DOI:10.1016/0040-4039(93)88021-A

Reference yield:

4-methylene-tetrahydro-pyran (36838-71-8) → {(1S,2S,4R)-2,4-Bis-(tert-butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-diphenyl-silanyloxy)-eth-(Z)-ylidene]-cyclohexyl}-methanol (146175-86-2)

Guidance literature:

Multi-step reaction with 11 steps

1: TiBr₂(OiPr)2, (R)-(+)-1,1'-bi-2-naphthol / CH₂Cl₂ / 240 h / -23 °C

2: 91 percent

3: LiAlH₄

4: pyridine

5: dimethylsulfoxide

6: 79 percent / DIBAL-H

7: 87 percent / MeAl(OMe)Cl / CH₂Cl₂ / -10 to 10 deg C

9: 95 percent / CrO₃, 3,5-dimethylpyrazole

10: 83 percent / NaBH₄, CeCl₃

11: 71 percent / imidazole / dimethylformamide

With pyridine; 1H-imidazole; 3,5-dimethyl-1H-pyrazole; chromium(VI) oxide; sodium tetrahydroborate; lithium aluminium tetrahydride; cerium(III) chloride; diisopropoxytitanium(IV) dibromide; (R)-1,1'-Bi-2-naphthol; (Methyl-methoxy-aluminium)-chlorid; diisobutylaluminium hydride; In dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide;

DOI:10.1016/0040-4039(93)88021-A

Reference yield:

Tetrahydro-4H-pyran-4-one (29943-42-8,143562-54-3) → {(1S,2S,4R)-2,4-Bis-(tert-butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-diphenyl-silanyloxy)-eth-(Z)-ylidene]-cyclohexyl}-methanol (146175-86-2)

Guidance literature:

Multi-step reaction with 12 steps

1: 75 percent / t-BuOK

2: TiBr₂(OiPr)2, (R)-(+)-1,1'-bi-2-naphthol / CH₂Cl₂ / 240 h / -23 °C

3: 91 percent

4: LiAlH₄

5: pyridine

6: dimethylsulfoxide

7: 79 percent / DIBAL-H

8: 87 percent / MeAl(OMe)Cl / CH₂Cl₂ / -10 to 10 deg C

10: 95 percent / CrO₃, 3,5-dimethylpyrazole

11: 83 percent / NaBH₄, CeCl₃

12: 71 percent / imidazole / dimethylformamide

With pyridine; 1H-imidazole; 3,5-dimethyl-1H-pyrazole; chromium(VI) oxide; sodium tetrahydroborate; lithium aluminium tetrahydride; cerium(III) chloride; diisopropoxytitanium(IV) dibromide; potassium tert-butylate; (R)-1,1'-Bi-2-naphthol; (Methyl-methoxy-aluminium)-chlorid; diisobutylaluminium hydride; In dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide;

DOI:10.1016/0040-4039(93)88021-A

upstream raw materials:

2-[(2S,3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-hydroxymethyl-cyclohex-(Z)-ylidene]-ethanol

tert-butylchlorodiphenylsilane

4-methylene-tetrahydro-pyran

Tetrahydro-4H-pyran-4-one

Downstream raw materials:

C₃₇H₆₀O₃Si₃

[3S-(1Z,3α,5β)]-2-[3,5-bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-2-methylenecyclohexylidene]ethanol