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

Base Information

Chemical Name:2-[(2S,3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-hydroxymethyl-cyclohex-(Z)-ylidene]-ethanol
CAS No.:146175-85-1
Molecular Formula:C₂₁H₄₄O₄Si₂
Molecular Weight:416.749
Hs Code.:

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

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

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

There total 18 articles about 2-[(2S,3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-hydroxymethyl-cyclohex-(Z)-ylidene]-ethanol 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: 83.0%

: 146175-84-0
(6R,8S,8aS)-6,8-Bis-(tert-butyl-dimethyl-silanyloxy)-1,5,6,7,8,8a-hexahydro-isochromen-3-one

: 146175-85-1
2-[(2S,3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-hydroxymethyl-cyclohex-(Z)-ylidene]-ethanol

Guidance literature:: With sodium tetrahydroborate; cerium(III) chloride;
DOI:10.1016/0040-4039(93)88021-A

Reference yield:

: 36838-71-8
4-methylene-tetrahydro-pyran

: 146175-85-1
2-[(2S,3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-hydroxymethyl-cyclohex-(Z)-ylidene]-ethanol

Guidance literature:: Multi-step reaction with 10 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

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

Reference yield:

: 29943-42-8,143562-54-3
Tetrahydro-4H-pyran-4-one

: 146175-85-1
2-[(2S,3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-hydroxymethyl-cyclohex-(Z)-ylidene]-ethanol

Guidance literature:: Multi-step reaction with 11 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

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