Acetic acid (1S,2R)-2-benzyloxy-1-{(R)-3-[5-(tert-butyl-dimethyl-silanyloxymethyl)-furan-2-yl]-2-methyl-3-oxo-propyl}-but-3-enyl ester

Base Information

Chemical Name:Acetic acid (1S,2R)-2-benzyloxy-1-{(R)-3-[5-(tert-butyl-dimethyl-silanyloxymethyl)-furan-2-yl]-2-methyl-3-oxo-propyl}-but-3-enyl ester
CAS No.:200264-92-2
Molecular Formula:C₂₈H₄₀O₆Si
Molecular Weight:500.707
Hs Code.:

Synonyms:Acetic acid (1S,2R)-2-benzyloxy-1-{(R)-3-[5-(tert-butyl-dimethyl-silanyloxymethyl)-furan-2-yl]-2-methyl-3-oxo-propyl}-but-3-enyl ester

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Chemical Property of Acetic acid (1S,2R)-2-benzyloxy-1-{(R)-3-[5-(tert-butyl-dimethyl-silanyloxymethyl)-furan-2-yl]-2-methyl-3-oxo-propyl}-but-3-enyl ester

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Technology Process of Acetic acid (1S,2R)-2-benzyloxy-1-{(R)-3-[5-(tert-butyl-dimethyl-silanyloxymethyl)-furan-2-yl]-2-methyl-3-oxo-propyl}-but-3-enyl ester

There total 7 articles about Acetic acid (1S,2R)-2-benzyloxy-1-{(R)-3-[5-(tert-butyl-dimethyl-silanyloxymethyl)-furan-2-yl]-2-methyl-3-oxo-propyl}-but-3-enyl 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: 97.0%

: 75-36-5
acetyl chloride

: 200264-91-1
(2R,4S,5R)-5-Benzyloxy-1-[5-(tert-butyl-dimethyl-silanyloxymethyl)-furan-2-yl]-4-hydroxy-2-methyl-hept-6-en-1-one

: 200264-92-2
Acetic acid (1S,2R)-2-benzyloxy-1-{(R)-3-[5-(tert-butyl-dimethyl-silanyloxymethyl)-furan-2-yl]-2-methyl-3-oxo-propyl}-but-3-enyl ester

Guidance literature:: With pyridine; In dichloromethane; at 0 ℃;
DOI:10.1021/ja972279y

Reference yield:

: 922-65-6
divinylcarbinol

: 200264-92-2
Acetic acid (1S,2R)-2-benzyloxy-1-{(R)-3-[5-(tert-butyl-dimethyl-silanyloxymethyl)-furan-2-yl]-2-methyl-3-oxo-propyl}-but-3-enyl ester

Guidance literature:: Multi-step reaction with 7 steps

1.1: 51 percent / (-)-DIPT; t-BuO₂H / Ti(Oi-Pr)4 / -15 °C

2.1: 95 percent / NaH; n-Bu₄NI / tetrahydrofuran

3.1: BF₃*OEt₂ / tetrahydrofuran / -78 °C

4.1: TsOH / CH₂Cl₂

5.1: LDA / -78 °C

6.1: n-BuLi / tetrahydrofuran / -78 °C

6.2: 98 percent / tetrahydrofuran

7.1: 97 percent / pyridine / CH₂Cl₂ / 0 °C

With pyridine; tert.-butylhydroperoxide; n-butyllithium; boron trifluoride diethyl etherate; tetra-(n-butyl)ammonium iodide; sodium hydride; D-(-)-diisopropyl tartrate; toluene-4-sulfonic acid; lithium diisopropyl amide; titanium(IV) isopropylate; In tetrahydrofuran; dichloromethane; 1.1: Epoxidation / 2.1: Etherification / 3.1: Ring cleavage / 4.1: Cyclization / 5.1: Metallation / 5.2: Methylation / 6.1: Metallation / 6.2: Addition / 7.1: Acetylation;
DOI:10.1021/ja972279y

Reference yield:

: 102490-00-6
(2S,3R)-1,2-epoxy-4-penten-3-ol

: 200264-92-2
Acetic acid (1S,2R)-2-benzyloxy-1-{(R)-3-[5-(tert-butyl-dimethyl-silanyloxymethyl)-furan-2-yl]-2-methyl-3-oxo-propyl}-but-3-enyl ester

Guidance literature:: Multi-step reaction with 6 steps

1.1: 95 percent / NaH; n-Bu₄NI / tetrahydrofuran

2.1: BF₃*OEt₂ / tetrahydrofuran / -78 °C

3.1: TsOH / CH₂Cl₂

4.1: LDA / -78 °C

5.1: n-BuLi / tetrahydrofuran / -78 °C

5.2: 98 percent / tetrahydrofuran

6.1: 97 percent / pyridine / CH₂Cl₂ / 0 °C

With pyridine; n-butyllithium; boron trifluoride diethyl etherate; tetra-(n-butyl)ammonium iodide; sodium hydride; toluene-4-sulfonic acid; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; 1.1: Etherification / 2.1: Ring cleavage / 3.1: Cyclization / 4.1: Metallation / 4.2: Methylation / 5.1: Metallation / 5.2: Addition / 6.1: Acetylation;
DOI:10.1021/ja972279y