[(2S,6R)-4-[2-(tert-Butyl-diphenyl-silanyloxy)-eth-(Z)-ylidene]-6-(4-methoxy-benzyloxymethyl)-tetrahydro-pyran-2-yl]-methanol

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Chemical Name:[(2S,6R)-4-[2-(tert-Butyl-diphenyl-silanyloxy)-eth-(Z)-ylidene]-6-(4-methoxy-benzyloxymethyl)-tetrahydro-pyran-2-yl]-methanol
CAS No.:290815-52-0
Molecular Formula:C₃₃H₄₂O₅Si
Molecular Weight:546.779
Hs Code.:

Synonyms:[(2S,6R)-4-[2-(tert-Butyl-diphenyl-silanyloxy)-eth-(Z)-ylidene]-6-(4-methoxy-benzyloxymethyl)-tetrahydro-pyran-2-yl]-methanol

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Chemical Property of [(2S,6R)-4-[2-(tert-Butyl-diphenyl-silanyloxy)-eth-(Z)-ylidene]-6-(4-methoxy-benzyloxymethyl)-tetrahydro-pyran-2-yl]-methanol

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Technology Process of [(2S,6R)-4-[2-(tert-Butyl-diphenyl-silanyloxy)-eth-(Z)-ylidene]-6-(4-methoxy-benzyloxymethyl)-tetrahydro-pyran-2-yl]-methanol

There total 15 articles about [(2S,6R)-4-[2-(tert-Butyl-diphenyl-silanyloxy)-eth-(Z)-ylidene]-6-(4-methoxy-benzyloxymethyl)-tetrahydro-pyran-2-yl]-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: 87.0%

: 290815-53-1
(E)-(R)-6-(tert-Butyl-diphenyl-silanyloxy)-1-(4-methoxy-benzyloxy)-4-(R)-1-oxiranylmethyl-hex-4-en-2-ol

: 290815-52-0
[(2S,6R)-4-[2-(tert-Butyl-diphenyl-silanyloxy)-eth-(Z)-ylidene]-6-(4-methoxy-benzyloxymethyl)-tetrahydro-pyran-2-yl]-methanol

Guidance literature:: With camphor-10-sulfonic acid; In dichloromethane; at 20 ℃; for 0.666667h;
DOI:10.1021/ol005850y

Reference yield:

: 290815-62-2
(R)-4-[(R)-1-(1,4-Dioxa-spiro[4.5]dec-2-yl)methyl]-6-hydroxymethyl-5,6-dihydro-pyran-2-one

: 290815-52-0
[(2S,6R)-4-[2-(tert-Butyl-diphenyl-silanyloxy)-eth-(Z)-ylidene]-6-(4-methoxy-benzyloxymethyl)-tetrahydro-pyran-2-yl]-methanol

Guidance literature:: Multi-step reaction with 7 steps

1: 88 percent / PPTS / CH₂Cl₂ / 8 h / 20 °C

2: 87 percent / NaBH₄; CeCl₃*7H₂O / methanol / 1.5 h / 0 °C

3: 95 percent / imidazole / dimethylformamide / 1 h / 0 °C

4: 81 percent / 1,3-propanedithiol; BF₃*Et₂O / CH₂Cl₂ / 1 h / -78 - -10 °C

5: 81 percent / collidine / CH₂Cl₂ / 4.5 h / 0 °C

6: NaH; imidazole / tetrahydrofuran / 0.3 h / 0 °C

7: 87 percent / CSA / CH₂Cl₂ / 0.67 h / 20 °C

With 1H-imidazole; 1.3-propanedithiol; 2,3,5-trimethyl-pyridine; sodium tetrahydroborate; cerium(III) chloride; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; pyridinium p-toluenesulfonate; sodium hydride; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; 1: Etherification / 2: Reduction / 3: Condensation / 4: Ring cleavage / 5: Condensation / 6: Cyclization / 7: intramolecular Williamson etherification;
DOI:10.1021/ol005850y

Reference yield:

: 290815-63-3
(R)-4-[(R)-1-(1,4-Dioxa-spiro[4.5]dec-2-yl)methyl]-6-(4-methoxy-benzyloxymethyl)-5,6-dihydro-pyran-2-one

: 290815-52-0
[(2S,6R)-4-[2-(tert-Butyl-diphenyl-silanyloxy)-eth-(Z)-ylidene]-6-(4-methoxy-benzyloxymethyl)-tetrahydro-pyran-2-yl]-methanol

Guidance literature:: Multi-step reaction with 6 steps

1: 87 percent / NaBH₄; CeCl₃*7H₂O / methanol / 1.5 h / 0 °C

2: 95 percent / imidazole / dimethylformamide / 1 h / 0 °C

3: 81 percent / 1,3-propanedithiol; BF₃*Et₂O / CH₂Cl₂ / 1 h / -78 - -10 °C

4: 81 percent / collidine / CH₂Cl₂ / 4.5 h / 0 °C

5: NaH; imidazole / tetrahydrofuran / 0.3 h / 0 °C

6: 87 percent / CSA / CH₂Cl₂ / 0.67 h / 20 °C

With 1H-imidazole; 1.3-propanedithiol; 2,3,5-trimethyl-pyridine; sodium tetrahydroborate; cerium(III) chloride; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; sodium hydride; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; 1: Reduction / 2: Condensation / 3: Ring cleavage / 4: Condensation / 5: Cyclization / 6: intramolecular Williamson etherification;
DOI:10.1021/ol005850y