Acetic acid (2S,4R,6S)-2-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-6-((S)-2-hydroxy-pent-4-enyl)-tetrahydro-pyran-4-yl ester

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Chemical Name:Acetic acid (2S,4R,6S)-2-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-6-((S)-2-hydroxy-pent-4-enyl)-tetrahydro-pyran-4-yl ester
CAS No.:288092-46-6
Molecular Formula:C₃₀H₄₂O₅Si
Molecular Weight:510.746
Hs Code.:

Synonyms:Acetic acid (2S,4R,6S)-2-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-6-((S)-2-hydroxy-pent-4-enyl)-tetrahydro-pyran-4-yl ester

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Chemical Property of Acetic acid (2S,4R,6S)-2-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-6-((S)-2-hydroxy-pent-4-enyl)-tetrahydro-pyran-4-yl ester

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Technology Process of Acetic acid (2S,4R,6S)-2-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-6-((S)-2-hydroxy-pent-4-enyl)-tetrahydro-pyran-4-yl ester

There total 7 articles about Acetic acid (2S,4R,6S)-2-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-6-((S)-2-hydroxy-pent-4-enyl)-tetrahydro-pyran-4-yl ester 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: 41.0%

: 85116-38-7
(+)-diisopinocampheylallylborane

: Acetic acid (2S,4R,6R)-2-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-6-(2-oxo-ethyl)-tetrahydro-pyran-4-yl ester

: Acetic acid (2R,4S,6R)-2-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-6-((S)-2-hydroxy-pent-4-enyl)-tetrahydro-pyran-4-yl ester

: 288092-46-6
Acetic acid (2S,4R,6S)-2-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-6-((S)-2-hydroxy-pent-4-enyl)-tetrahydro-pyran-4-yl ester

Guidance literature:: (+)-diisopinocampheylallylborane; Acetic acid (2S,4R,6R)-2-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-6-(2-oxo-ethyl)-tetrahydro-pyran-4-yl ester; In diethyl ether; at -78 - 20 ℃;

With sodium perborate;
DOI:10.1016/S0040-4039(00)00530-X

Reference yield:

: 112897-03-7
3-(tert-butyldiphenylsilyloxy)-1-propanal

: 288092-46-6
Acetic acid (2S,4R,6S)-2-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-6-((S)-2-hydroxy-pent-4-enyl)-tetrahydro-pyran-4-yl ester

Guidance literature:: Multi-step reaction with 7 steps

1.1: 71 percent / BF₃*Et₂O; CF₃CO₂H

2.1: Hg(OAc)2

2.2: 69 percent / NaBH₃CN / tetrahydrofuran

3.1: LiAl(Ot-Bu)3H

4.1: NaOAc

5.1: 73 percent / TMSOTf / acetonitrile

6.1: 89 percent / O₃; PPh₃ / CH₂Cl₂ / -78 °C

7.1: diethyl ether / -78 - 20 °C

7.2: 42 percent / NaBO₃

With trimethylsilyl trifluoromethanesulfonate; boron trifluoride diethyl etherate; mercury(II) diacetate; sodium acetate; ozone; lithium tri-t-butoxyaluminum hydride; triphenylphosphine; trifluoroacetic acid; In diethyl ether; dichloromethane; acetonitrile; 1.1: cyclocondensation / 2.1: oxymercuration / 2.2: Reduction / 3.1: Reduction / 4.1: Acetylation / 5.1: Substitution / 6.1: ozonolysis / 7.1: Substitution / 7.2: Oxidation;
DOI:10.1016/S0040-4039(00)00530-X

Reference yield:

: 288092-41-1
2-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2,3-dihydro-pyran-4-one

: 288092-46-6
Acetic acid (2S,4R,6S)-2-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-6-((S)-2-hydroxy-pent-4-enyl)-tetrahydro-pyran-4-yl ester

Guidance literature:: Multi-step reaction with 6 steps

1.1: Hg(OAc)2

1.2: 69 percent / NaBH₃CN / tetrahydrofuran

2.1: LiAl(Ot-Bu)3H

3.1: NaOAc

4.1: 73 percent / TMSOTf / acetonitrile

5.1: 89 percent / O₃; PPh₃ / CH₂Cl₂ / -78 °C

6.1: diethyl ether / -78 - 20 °C

6.2: 42 percent / NaBO₃

With trimethylsilyl trifluoromethanesulfonate; mercury(II) diacetate; sodium acetate; ozone; lithium tri-t-butoxyaluminum hydride; triphenylphosphine; In diethyl ether; dichloromethane; acetonitrile; 1.1: oxymercuration / 1.2: Reduction / 2.1: Reduction / 3.1: Acetylation / 4.1: Substitution / 5.1: ozonolysis / 6.1: Substitution / 6.2: Oxidation;
DOI:10.1016/S0040-4039(00)00530-X