Acetic acid (1S,2R,3S,4S,6R)-4-benzyloxy-3-methyl-2-(tetrahydro-pyran-2-yloxymethyl)-3-vinyl-7-oxa-bicyclo[4.2.0]oct-1-yl ester

Base Information

Chemical Name:Acetic acid (1S,2R,3S,4S,6R)-4-benzyloxy-3-methyl-2-(tetrahydro-pyran-2-yloxymethyl)-3-vinyl-7-oxa-bicyclo[4.2.0]oct-1-yl ester
CAS No.:326922-44-5
Molecular Formula:C₂₅H₃₄O₆
Molecular Weight:430.541
Hs Code.:

Synonyms:Acetic acid (1S,2R,3S,4S,6R)-4-benzyloxy-3-methyl-2-(tetrahydro-pyran-2-yloxymethyl)-3-vinyl-7-oxa-bicyclo[4.2.0]oct-1-yl ester

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Chemical Property of Acetic acid (1S,2R,3S,4S,6R)-4-benzyloxy-3-methyl-2-(tetrahydro-pyran-2-yloxymethyl)-3-vinyl-7-oxa-bicyclo[4.2.0]oct-1-yl ester

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Technology Process of Acetic acid (1S,2R,3S,4S,6R)-4-benzyloxy-3-methyl-2-(tetrahydro-pyran-2-yloxymethyl)-3-vinyl-7-oxa-bicyclo[4.2.0]oct-1-yl ester

There total 20 articles about Acetic acid (1S,2R,3S,4S,6R)-4-benzyloxy-3-methyl-2-(tetrahydro-pyran-2-yloxymethyl)-3-vinyl-7-oxa-bicyclo[4.2.0]oct-1-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: 100.0%

: 108-24-7
acetic anhydride

: 326922-43-4
(1S,2R,3S,4S,6R)-4-Benzyloxy-3-methyl-2-(tetrahydro-pyran-2-yloxymethyl)-3-vinyl-7-oxa-bicyclo[4.2.0]octan-1-ol

: 326922-44-5
Acetic acid (1S,2R,3S,4S,6R)-4-benzyloxy-3-methyl-2-(tetrahydro-pyran-2-yloxymethyl)-3-vinyl-7-oxa-bicyclo[4.2.0]oct-1-yl ester

Guidance literature:: With pyridine; dmap; at 40 ℃;
DOI:10.1039/b006170k

Reference yield:

: 100-39-0
benzyl bromide

: 326922-44-5
Acetic acid (1S,2R,3S,4S,6R)-4-benzyloxy-3-methyl-2-(tetrahydro-pyran-2-yloxymethyl)-3-vinyl-7-oxa-bicyclo[4.2.0]oct-1-yl ester

Guidance literature:: Multi-step reaction with 15 steps

1.1: NaH / dimethylformamide / 0 °C

1.2: 80 percent / n-Bu₄NI / dimethylformamide / 0 °C

2.1: Hg(OCOCF₃)2 / acetone; H₂O / 0 °C

2.2: 80 percent / MsCl; Et₃N / CH₂Cl₂ / 0 °C

3.1: diethyl ether / -78 °C

4.1: PCC; 4 Angstroem molecular sieves / CH₂Cl₂ / 20 °C

5.1: CuCN / diethyl ether / 0.17 h / -78 °C

5.2: 62 percent / tetrahydrofuran; diethyl ether / 0.25 h / -60 °C

6.1: 90 percent / PPTS / CH₂Cl₂ / 20 °C

7.1: 53 percent

8.1: tetrahydrofuran / 20 °C

8.2: 64 percent / K₂CO₃ / methanol / 20 °C

9.1: 81 percent / t-BuOOH / VO(acac)2 / 20 °C

10.1: AcOK; 18-crown-6 / dimethylformamide / 100 °C

11.1: pyridine / 20 °C

12.1: 96 percent / DMAP / CH₂Cl₂ / 20 °C

13.1: K₂CO₃ / methanol / 20 °C

14.1: DBU / toluene / 100 °C

15.1: 100 percent / DMAP; pyridine / 40 °C

With pyridine; tert.-butylhydroperoxide; dmap; 18-crown-6 ether; 4 A molecular sieve; potassium acetate; mercury(II) trifluoroacetate; pyridinium p-toluenesulfonate; sodium hydride; potassium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; pyridinium chlorochromate; bis(acetylacetonate)oxovanadium; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; 2.1: Ferrier's carbocyclization;
DOI:10.1039/b006170k

Reference yield:

: 136611-27-3
4-<(benzyl)oxy>-3-methyl-2-cyclohexenone

: 326922-44-5
Acetic acid (1S,2R,3S,4S,6R)-4-benzyloxy-3-methyl-2-(tetrahydro-pyran-2-yloxymethyl)-3-vinyl-7-oxa-bicyclo[4.2.0]oct-1-yl ester

Guidance literature:: Multi-step reaction with 11 steps

1.1: CuCN / diethyl ether / 0.17 h / -78 °C

1.2: 62 percent / tetrahydrofuran; diethyl ether / 0.25 h / -60 °C

2.1: 90 percent / PPTS / CH₂Cl₂ / 20 °C

3.1: 53 percent

4.1: tetrahydrofuran / 20 °C

4.2: 64 percent / K₂CO₃ / methanol / 20 °C

5.1: 81 percent / t-BuOOH / VO(acac)2 / 20 °C

6.1: AcOK; 18-crown-6 / dimethylformamide / 100 °C

7.1: pyridine / 20 °C

8.1: 96 percent / DMAP / CH₂Cl₂ / 20 °C

9.1: K₂CO₃ / methanol / 20 °C

10.1: DBU / toluene / 100 °C

11.1: 100 percent / DMAP; pyridine / 40 °C

With pyridine; tert.-butylhydroperoxide; dmap; 18-crown-6 ether; potassium acetate; pyridinium p-toluenesulfonate; potassium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; bis(acetylacetonate)oxovanadium; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1039/b006170k