Benzoic acid (2R,3S,4R,6R)-4-dimethylamino-6-(1-hydroxy-9,10-dioxo-9,10-dihydro-anthracen-2-ylmethoxy)-2-methyl-tetrahydro-pyran-3-yl ester

Base Information

Chemical Name:Benzoic acid (2R,3S,4R,6R)-4-dimethylamino-6-(1-hydroxy-9,10-dioxo-9,10-dihydro-anthracen-2-ylmethoxy)-2-methyl-tetrahydro-pyran-3-yl ester
CAS No.:309722-48-3
Molecular Formula:C₃₀H₂₉NO₇
Molecular Weight:515.563
Hs Code.:

Synonyms:Benzoic acid (2R,3S,4R,6R)-4-dimethylamino-6-(1-hydroxy-9,10-dioxo-9,10-dihydro-anthracen-2-ylmethoxy)-2-methyl-tetrahydro-pyran-3-yl ester

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Chemical Property of Benzoic acid (2R,3S,4R,6R)-4-dimethylamino-6-(1-hydroxy-9,10-dioxo-9,10-dihydro-anthracen-2-ylmethoxy)-2-methyl-tetrahydro-pyran-3-yl ester

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Technology Process of Benzoic acid (2R,3S,4R,6R)-4-dimethylamino-6-(1-hydroxy-9,10-dioxo-9,10-dihydro-anthracen-2-ylmethoxy)-2-methyl-tetrahydro-pyran-3-yl ester

There total 3 articles about Benzoic acid (2R,3S,4R,6R)-4-dimethylamino-6-(1-hydroxy-9,10-dioxo-9,10-dihydro-anthracen-2-ylmethoxy)-2-methyl-tetrahydro-pyran-3-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: 65.0%

: 24094-45-9
digiferruginol

: 309722-45-0
Benzoic acid (2R,3S,4R)-6-acetoxy-4-dimethylamino-2-methyl-tetrahydro-pyran-3-yl ester

: 309722-48-3
Benzoic acid (2R,3S,4R,6R)-4-dimethylamino-6-(1-hydroxy-9,10-dioxo-9,10-dihydro-anthracen-2-ylmethoxy)-2-methyl-tetrahydro-pyran-3-yl ester

: 309722-47-2
Benzoic acid (2R,3S,4R,6S)-4-dimethylamino-6-(1-hydroxy-9,10-dioxo-9,10-dihydro-anthracen-2-ylmethoxy)-2-methyl-tetrahydro-pyran-3-yl ester

Guidance literature:: With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; In tetrahydrofuran; at 0 ℃; for 0.666667h;
DOI:10.1016/S0960-894X(00)00410-8

Reference yield:

: 9,10-dimethoxy-9,10-dihydroanthracen-1-ol

: 309722-48-3
Benzoic acid (2R,3S,4R,6R)-4-dimethylamino-6-(1-hydroxy-9,10-dioxo-9,10-dihydro-anthracen-2-ylmethoxy)-2-methyl-tetrahydro-pyran-3-yl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 98 percent / Sc(OTf)3 / H₂O; tetrahydrofuran / 7 h / 25 °C

2: 59 percent / CAN / acetonitrile; H₂O / 0.25 h / -17 °C

3: 24 percent / TMSTOf; 4 Angstroem sieves / tetrahydrofuran / 0.67 h / 0 °C

With ammonium cerium(IV) nitrate; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; scandium tris(trifluoromethanesulfonate); In tetrahydrofuran; water; acetonitrile; 1: Hydroxymethylation / 2: Oxidation / 3: Glycosylation;
DOI:10.1016/S0960-894X(00)00410-8

Reference yield:

: 2-hydroxymethyl-9,10-dimethoxy-9,10-dihydro-anthracen-1-ol

: 309722-48-3
Benzoic acid (2R,3S,4R,6R)-4-dimethylamino-6-(1-hydroxy-9,10-dioxo-9,10-dihydro-anthracen-2-ylmethoxy)-2-methyl-tetrahydro-pyran-3-yl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 59 percent / CAN / acetonitrile; H₂O / 0.25 h / -17 °C

2: 24 percent / TMSTOf; 4 Angstroem sieves / tetrahydrofuran / 0.67 h / 0 °C

With ammonium cerium(IV) nitrate; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; In tetrahydrofuran; water; acetonitrile; 1: Oxidation / 2: Glycosylation;
DOI:10.1016/S0960-894X(00)00410-8