(1S,4S,6R,7R)-benzoic acid 4-benzoyloxymethyl-6-hydroxy-2-oxabicyclo[2.2.1]hept-7-yl ester

Base Information

Chemical Name:(1S,4S,6R,7R)-benzoic acid 4-benzoyloxymethyl-6-hydroxy-2-oxabicyclo[2.2.1]hept-7-yl ester
CAS No.:544444-34-0
Molecular Formula:C₂₁H₂₀O₆
Molecular Weight:368.386
Hs Code.:

Synonyms:(1S,4S,6R,7R)-benzoic acid 4-benzoyloxymethyl-6-hydroxy-2-oxabicyclo[2.2.1]hept-7-yl ester

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Chemical Property of (1S,4S,6R,7R)-benzoic acid 4-benzoyloxymethyl-6-hydroxy-2-oxabicyclo[2.2.1]hept-7-yl ester

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Technology Process of (1S,4S,6R,7R)-benzoic acid 4-benzoyloxymethyl-6-hydroxy-2-oxabicyclo[2.2.1]hept-7-yl ester

There total 7 articles about (1S,4S,6R,7R)-benzoic acid 4-benzoyloxymethyl-6-hydroxy-2-oxabicyclo[2.2.1]hept-7-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: 83.0%

: 544444-33-9
(1R,4S,6R,7R)-benzoic acid 7-benzoyloxy-6-(tert-butyldiphenylsilanyloxy)-2-oxabicyclo[2.2.1]hept-4-ylmethyl ester

: 544444-34-0
(1S,4S,6R,7R)-benzoic acid 4-benzoyloxymethyl-6-hydroxy-2-oxabicyclo[2.2.1]hept-7-yl ester

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 12h;
DOI:10.1021/ol034326z

Reference yield:

: 544444-28-2
(1R,4R)-4-Benzyloxymethyl-4-hydroxymethylcyclopent-2-en-1-ol

: 544444-34-0
(1S,4S,6R,7R)-benzoic acid 4-benzoyloxymethyl-6-hydroxy-2-oxabicyclo[2.2.1]hept-7-yl ester

Guidance literature:: Multi-step reaction with 7 steps

1.1: 76 percent / DMAP; Et₃N / CH₂Cl₂ / 20 °C

2.1: 94 percent / OsO₄; N-methylmorpholine N-oxide monohydrate / acetone; H₂O / 20 °C

3.1: 95 percent / Et₃N; DMAP / CH₂Cl₂ / 5 °C

4.1: 87 percent / formic acid / palladium black / methanol / 4 h / 75 °C

5.1: Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

6.1: K₂CO₃ / methanol / 5 - 20 °C

6.2: 53 percent / Et₃N / CH₂Cl₂ / 0 °C

7.1: 83 percent / TBAF / tetrahydrofuran / 12 h / 20 °C

With dmap; osmium(VIII) oxide; formic acid; tetrabutyl ammonium fluoride; potassium carbonate; 4-methylmorpholine N-oxide; triethylamine; palladium; In tetrahydrofuran; methanol; dichloromethane; water; acetone;
DOI:10.1021/ol034326z

Reference yield:

: 544444-38-4
[(1R,4R)-1-Benzyloxymethyl-4-(tert-butyl-diphenyl-silanyloxy)-cyclopent-2-enyl]-methanol

: 544444-34-0
(1S,4S,6R,7R)-benzoic acid 4-benzoyloxymethyl-6-hydroxy-2-oxabicyclo[2.2.1]hept-7-yl ester

Guidance literature:: Multi-step reaction with 6 steps

1.1: 94 percent / OsO₄; N-methylmorpholine N-oxide monohydrate / acetone; H₂O / 20 °C

2.1: 95 percent / Et₃N; DMAP / CH₂Cl₂ / 5 °C

3.1: 87 percent / formic acid / palladium black / methanol / 4 h / 75 °C

4.1: Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

5.1: K₂CO₃ / methanol / 5 - 20 °C

5.2: 53 percent / Et₃N / CH₂Cl₂ / 0 °C

6.1: 83 percent / TBAF / tetrahydrofuran / 12 h / 20 °C

With dmap; osmium(VIII) oxide; formic acid; tetrabutyl ammonium fluoride; potassium carbonate; 4-methylmorpholine N-oxide; triethylamine; palladium; In tetrahydrofuran; methanol; dichloromethane; water; acetone;
DOI:10.1021/ol034326z