(2R,4aR,5S,7R,8aR,9aS,10aS)-7-Allyl-5-benzyloxy-10a-methyl-2-phenyl-octahydro-1,3,8,10-tetraoxa-anthracene

Base Information

Chemical Name:(2R,4aR,5S,7R,8aR,9aS,10aS)-7-Allyl-5-benzyloxy-10a-methyl-2-phenyl-octahydro-1,3,8,10-tetraoxa-anthracene
CAS No.:629645-75-6
Molecular Formula:C₂₇H₃₂O₅
Molecular Weight:436.548
Hs Code.:

Synonyms:(2R,4aR,5S,7R,8aR,9aS,10aS)-7-Allyl-5-benzyloxy-10a-methyl-2-phenyl-octahydro-1,3,8,10-tetraoxa-anthracene

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Chemical Property of (2R,4aR,5S,7R,8aR,9aS,10aS)-7-Allyl-5-benzyloxy-10a-methyl-2-phenyl-octahydro-1,3,8,10-tetraoxa-anthracene

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Technology Process of (2R,4aR,5S,7R,8aR,9aS,10aS)-7-Allyl-5-benzyloxy-10a-methyl-2-phenyl-octahydro-1,3,8,10-tetraoxa-anthracene

There total 7 articles about (2R,4aR,5S,7R,8aR,9aS,10aS)-7-Allyl-5-benzyloxy-10a-methyl-2-phenyl-octahydro-1,3,8,10-tetraoxa-anthracene 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%

: 100-39-0
benzyl bromide

: 630102-83-9
(2R,4aR,5S,7R,8aR,9aS,10aS)-7-Allyl-10a-methyl-2-phenyl-octahydro-1,3,8,10-tetraoxa-anthracen-5-ol

: 629645-75-6
(2R,4aR,5S,7R,8aR,9aS,10aS)-7-Allyl-5-benzyloxy-10a-methyl-2-phenyl-octahydro-1,3,8,10-tetraoxa-anthracene

Guidance literature:: With potassium hydride; In tetrahydrofuran; at 20 ℃;
DOI:10.1016/j.tetlet.2003.09.003

Reference yield:

: 131310-61-7
(2R,4aR,6S,7R,8aS)-6-Methyl-2-phenyl-6-vinyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol

: 629645-75-6
(2R,4aR,5S,7R,8aR,9aS,10aS)-7-Allyl-5-benzyloxy-10a-methyl-2-phenyl-octahydro-1,3,8,10-tetraoxa-anthracene

Guidance literature:: Multi-step reaction with 7 steps

1.1: O₃ / methanol / -78 °C

1.2: Me₂S / methanol

2.1: Zn powder; satd. NH₄Cl / tetrahydrofuran / 0 °C

3.1: O₃ / CH₂Cl₂ / -78 °C

3.2: PPh₃ / CH₂Cl₂

4.1: pyridine; DMAP / CH₂Cl₂ / Heating

5.1: 65 percent / BF₃*OEt₂ / acetonitrile / 0 °C

6.1: 98 percent / NaOMe / methanol / 20 °C

7.1: 100 percent / KH / tetrahydrofuran / 20 °C

With pyridine; dmap; boron trifluoride diethyl etherate; sodium methylate; potassium hydride; ammonium chloride; ozone; zinc; In tetrahydrofuran; methanol; dichloromethane; acetonitrile; 2.1: Barbier allylation;
DOI:10.1016/j.tetlet.2003.09.003

Reference yield:

: (2R,4aR,6R,7R,8aS)-7-Hydroxy-6-methyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine-6-carbaldehyde

: 629645-75-6
(2R,4aR,5S,7R,8aR,9aS,10aS)-7-Allyl-5-benzyloxy-10a-methyl-2-phenyl-octahydro-1,3,8,10-tetraoxa-anthracene

Guidance literature:: Multi-step reaction with 6 steps

1.1: Zn powder; satd. NH₄Cl / tetrahydrofuran / 0 °C

2.1: O₃ / CH₂Cl₂ / -78 °C

2.2: PPh₃ / CH₂Cl₂

3.1: pyridine; DMAP / CH₂Cl₂ / Heating

4.1: 65 percent / BF₃*OEt₂ / acetonitrile / 0 °C

5.1: 98 percent / NaOMe / methanol / 20 °C

6.1: 100 percent / KH / tetrahydrofuran / 20 °C

With pyridine; dmap; boron trifluoride diethyl etherate; sodium methylate; potassium hydride; ammonium chloride; ozone; zinc; In tetrahydrofuran; methanol; dichloromethane; acetonitrile; 1.1: Barbier allylation;
DOI:10.1016/j.tetlet.2003.09.003