Acetic acid (4S,4aR,6R,7R,8R,8aS)-6-allyloxy-7-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2-(4-methoxy-phenyl)-4-methyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester

Base Information

Chemical Name:Acetic acid (4S,4aR,6R,7R,8R,8aS)-6-allyloxy-7-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2-(4-methoxy-phenyl)-4-methyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester
CAS No.:827611-35-8
Molecular Formula:C₂₈H₂₉NO₉
Molecular Weight:523.54
Hs Code.:

Acetic acid (4S,4aR,6R,7R,8R,8aS)-6-allyloxy-7-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2-(4-methoxy-phenyl)-4-methyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester

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Chemical Property of Acetic acid (4S,4aR,6R,7R,8R,8aS)-6-allyloxy-7-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2-(4-methoxy-phenyl)-4-methyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester

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Technology Process of Acetic acid (4S,4aR,6R,7R,8R,8aS)-6-allyloxy-7-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2-(4-methoxy-phenyl)-4-methyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester

There total 8 articles about Acetic acid (4S,4aR,6R,7R,8R,8aS)-6-allyloxy-7-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2-(4-methoxy-phenyl)-4-methyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-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:

: 2186-92-7
p-Anisaldehyde dimethyl acetal

: 428499-65-4
allyl (6S)-3-O-acetyl-2-deoxy-6-C-methyl-2-phthalimido-β-D-glucopyranoside

: 827611-35-8
Acetic acid (4S,4aR,6R,7R,8R,8aS)-6-allyloxy-7-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2-(4-methoxy-phenyl)-4-methyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester

Guidance literature:: With 4 A molecular sieve; camphor-10-sulfonic acid; In toluene; at 90 ℃;
DOI:10.1016/S0008-6215(01)00295-6

Reference yield:

: 428499-79-0
allyl 3-O-acetyl-6-O-(tert-butyldimethylsilyl)-2-deoxy-2-phthalimido-β-D-glucopyranoside

: 827611-35-8
Acetic acid (4S,4aR,6R,7R,8R,8aS)-6-allyloxy-7-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2-(4-methoxy-phenyl)-4-methyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester

Guidance literature:: Multi-step reaction with 7 steps

1.1: PPTS

2.1: nBu₄NF / tetrahydrofuran

3.1: 64 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 0 °C

4.1: CuCN / tetrahydrofuran / -45 - 20 °C

4.2: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 0 °C

5.1: iBu₂AlH; ZnCl₂ / tetrahydrofuran / -78 °C

6.1: p-TsOH / methanol

7.1: camphorsulfonic acid; 4 Angstroem molecular sieves / toluene / 90 °C

With oxalyl dichloride; 4 A molecular sieve; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; zinc(II) chloride; In tetrahydrofuran; methanol; dichloromethane; toluene; 3.1: Swern oxidation / 4.2: Swern oxidation;
DOI:10.1016/S0008-6215(01)00295-6

Reference yield:

: 428499-63-2
Acetic acid (2R,3R,4R,5S,6S)-2-allyloxy-3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-formyl-5-(tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yl ester

: 827611-35-8
Acetic acid (4S,4aR,6R,7R,8R,8aS)-6-allyloxy-7-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2-(4-methoxy-phenyl)-4-methyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: CuCN / tetrahydrofuran / -45 - 20 °C

1.2: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 0 °C

2.1: iBu₂AlH; ZnCl₂ / tetrahydrofuran / -78 °C

3.1: p-TsOH / methanol

4.1: camphorsulfonic acid; 4 Angstroem molecular sieves / toluene / 90 °C

With 4 A molecular sieve; camphor-10-sulfonic acid; diisobutylaluminium hydride; toluene-4-sulfonic acid; zinc(II) chloride; In tetrahydrofuran; methanol; toluene; 1.2: Swern oxidation;
DOI:10.1016/S0008-6215(01)00295-6