Acetic acid (1S,2R,3S,4S,6S)-4-benzyloxy-1,6-dihydroxy-3-methyl-2-(tetrahydro-pyran-2-yloxymethyl)-3-vinyl-cyclohexylmethyl ester

Base Information

Chemical Name:Acetic acid (1S,2R,3S,4S,6S)-4-benzyloxy-1,6-dihydroxy-3-methyl-2-(tetrahydro-pyran-2-yloxymethyl)-3-vinyl-cyclohexylmethyl ester
CAS No.:326922-41-2
Molecular Formula:C₂₅H₃₆O₇
Molecular Weight:448.557
Hs Code.:

Synonyms:Acetic acid (1S,2R,3S,4S,6S)-4-benzyloxy-1,6-dihydroxy-3-methyl-2-(tetrahydro-pyran-2-yloxymethyl)-3-vinyl-cyclohexylmethyl ester

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Chemical Property of Acetic acid (1S,2R,3S,4S,6S)-4-benzyloxy-1,6-dihydroxy-3-methyl-2-(tetrahydro-pyran-2-yloxymethyl)-3-vinyl-cyclohexylmethyl ester

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Technology Process of Acetic acid (1S,2R,3S,4S,6S)-4-benzyloxy-1,6-dihydroxy-3-methyl-2-(tetrahydro-pyran-2-yloxymethyl)-3-vinyl-cyclohexylmethyl ester

There total 16 articles about Acetic acid (1S,2R,3S,4S,6S)-4-benzyloxy-1,6-dihydroxy-3-methyl-2-(tetrahydro-pyran-2-yloxymethyl)-3-vinyl-cyclohexylmethyl 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:

: 100-39-0
benzyl bromide

: 326922-41-2
Acetic acid (1S,2R,3S,4S,6S)-4-benzyloxy-1,6-dihydroxy-3-methyl-2-(tetrahydro-pyran-2-yloxymethyl)-3-vinyl-cyclohexylmethyl ester

Guidance literature:: Multi-step reaction with 11 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

With pyridine; tert.-butylhydroperoxide; 18-crown-6 ether; 4 A molecular sieve; potassium acetate; mercury(II) trifluoroacetate; pyridinium p-toluenesulfonate; sodium hydride; pyridinium chlorochromate; bis(acetylacetonate)oxovanadium; In tetrahydrofuran; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; acetone; 2.1: Ferrier's carbocyclization;
DOI:10.1039/b006170k

Reference yield:

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

: 326922-41-2
Acetic acid (1S,2R,3S,4S,6S)-4-benzyloxy-1,6-dihydroxy-3-methyl-2-(tetrahydro-pyran-2-yloxymethyl)-3-vinyl-cyclohexylmethyl ester

Guidance literature:: Multi-step reaction with 7 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

With pyridine; tert.-butylhydroperoxide; 18-crown-6 ether; potassium acetate; pyridinium p-toluenesulfonate; bis(acetylacetonate)oxovanadium; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1039/b006170k

Reference yield:

: 23339-17-5
methyl 4,6-di-O-acetyl-2,3-dideoxy-D-erythro-hexopyranoside

: 326922-41-2
Acetic acid (1S,2R,3S,4S,6S)-4-benzyloxy-1,6-dihydroxy-3-methyl-2-(tetrahydro-pyran-2-yloxymethyl)-3-vinyl-cyclohexylmethyl ester

Guidance literature:: Multi-step reaction with 12 steps

1.1: NaOMe / methanol / 0 °C

1.2: 87 percent / I₂; PPh₃; imidazole / tetrahydrofuran / 20 °C

2.1: NaH / dimethylformamide / 0 °C

2.2: 80 percent / n-Bu₄NI / dimethylformamide / 0 °C

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

3.2: 80 percent / MsCl; Et₃N / CH₂Cl₂ / 0 °C

4.1: diethyl ether / -78 °C

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

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

6.2: 62 percent / tetrahydrofuran; diethyl ether / 0.25 h / -60 °C

7.1: 90 percent / PPTS / CH₂Cl₂ / 20 °C

8.1: 53 percent

9.1: tetrahydrofuran / 20 °C

9.2: 64 percent / K₂CO₃ / methanol / 20 °C

10.1: 81 percent / t-BuOOH / VO(acac)2 / 20 °C

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

12.1: pyridine / 20 °C

With pyridine; tert.-butylhydroperoxide; 18-crown-6 ether; 4 A molecular sieve; sodium methylate; potassium acetate; mercury(II) trifluoroacetate; pyridinium p-toluenesulfonate; sodium hydride; pyridinium chlorochromate; bis(acetylacetonate)oxovanadium; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; acetone; 3.1: Ferrier's carbocyclization;
DOI:10.1039/b006170k